Explore every episode of the podcast The GTMnow Podcast
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Title
Pub. Date
Duration
How Datarails Grew 30x in 5 Years (90% Outbound → 90% Inbound) | Aviv Canaani (CRO & CMO)
21 oct. 2026
00:40:17
Today marks Aviv Canaani’s 5-year anniversary at Datarails! When he first joined Datarails five years ago, the company was 90% outbound, with analysts emailing inbound leads to SDRs once a week. Today it’s 90% inbound, 30x bigger, $70M Series C, and The Information named it the #1 startup of the year.
Transcript: Full interview transcripts can be found by episode at https://gtmnow.com/tag/podcast/
What you’ll learn: - How Datarails flipped from 90% outbound to 90% inbound, and why they doubled down on inbound after the 2022 crash - The Gong-inspired brand playbook: why “98% of marketing is noise” and how to be the 1% people care about - Why niche memes for 0.1% of the market work (FP&A vs. accounting in-jokes) - How to prove brand ROI: the four-way attribution model (HubSpot, open-form website question, SDR ask, Gong calls) - Why his VP of Brand is the only report with no revenue KPIs, and how he measures brand instead (engagement from the ICP) - The marketer-to-CRO path, and why he thinks one person owning the whole funnel is the future - The “revenue architecture” waterfall model: working backward from a number to channels, meetings, and cost - Why they killed their own category and relaunched as a “Finance OS,” and how to pull off category creation - How he hires: the “biggest accomplishment” question, and screening for ownership over blame - Why he automates everything in sales so reps only show up, follow up, and sell
Sophie Buonassisi, Partner at GTMfund LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ X: https://x.com/sophiebuona
About the guest: Aviv Canaani is the CRO and CMO of Datarails, an FP&A platform the company now positions as a “Finance OS.” He joined roughly five years ago as its first marketing leader (VP of Marketing), later took over sales, and was promoted to CRO, overseeing the full revenue funnel across marketing, sales, growth, and partnerships. Under his tenure Datarails grew about 30x and was named a top startup of the year by The Information.
About GTMnow: The media brand, GTMnow, shares how the best companies get built, told from every perspective: founders, operators and investors, at every stage of company building. GTMnow is owned and operated by VC firm, GTMfund.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
The ex-engineer who says sales beats product | George Kurdin (CEO, Monk)
14 oct. 2026
00:32:51
George was a professional poker player, then CEO of a company that sold to Logitech for around $100M, and now he’s the CEO of Monk, an AI company automating accounts receivable.
Monk is an API company solving the other side of the ledger from Ramp: getting B2B invoices paid. George gets candid about the go-to-market mistakes he made (“50 more than I expected”), why vertical companies win on in-person workshops, the proprietary “harness” that he argues is the real moat in applied AI, the extreme-accountability culture he runs with 16 people and almost no meetings, and his sharpest tactical advice on fundraising, websites, and co-founder relationships.
Brought to you by: Nooks - discover how revenue agents can transform your GTM at https://nooks.ai/gtmfund
What you’ll learn: - Why sales and marketing is “tier zero,” and why he used to believe the opposite (“if you build it, they will come” is wrong) - Two lessons from pro poker that transfer to building: stay disciplined through variance, and adapt or get destroyed - Why go-to-market has never been more nuanced, and why vertical companies are winning with in-person workshops and lunch-and-learns over cold email - The pre-seed website bet: why spending big on a cohesive visual identity early lifted one company’s close rate ~50% - The “harness” thesis: why owning your own evals, guardrails, and tests (not just calling the models) is the moat in applied AI - How to run extreme accountability: everything in Slack, blameless retros, almost no meetings, 16 people - Why they reverse-engineered into a huge-TAM problem on purpose (recruiting, and not getting disrupted by the frontier labs) - Why hard ROI (dollars in your pocket) now beats “time savings” as an AI value prop - Fundraising: compress the process to create FOMO, and why how you run the raise signals how you run the company - Why the co-founder relationship matters more than the idea, and how to invest in it like a marriage
About the guest: George is the co-founder and CEO of Monk, an API company that automates accounts receivable (collections and cash application) for B2B businesses using AI. He was previously CEO of Streamlabs, which sold to Logitech (reported around $100M) in 2019, and before his operating career he was a professional poker player for about five years. Monk is based in New York and has raised roughly $28M, including a Series A. His co-founder is Joe.
About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Legora's CRO: $3.5M to $200M+ ARR, the Fastest Direct Sales Motion | Patrick Forquer
06 oct. 2026
00:51:46
Legora went from $3.5M to over $100M in revenue in about a year, the fastest any company has ever scaled a direct-sales motion from zero to $100M. Then, they doubled revenue in less than 6 months and hit $200M ARR.
Patrick spent seven years at Braze, from the early days through IPO, before joining Legora (a vertical legal-AI company founded by Max, backed by Benchmark and Redpoint) at $3.5M in revenue. He shares the scaling journey. He also gets tactical on the three things he looks for before joining a company, why speed-to-value is the number-one leading indicator of revenue performance, the pilot that lets customers keep everything they build even if they walk, how he structures forward-deploy across legal engineers and traditional FDEs, the Jude Law and Aaron Judge campaigns and whether they paid off, the "8 Mile" objection-handling play, and the shift to consumption pricing.
Brought to you by: Nooks - discover how revenue agents can transform your GTM athttps://nooks.ai/gtmfund
About the guest: Patrick Faucher is the CRO of Legora. He joined at roughly $3.5M in revenue and helped scale it past $100M in about a year, the fastest any company has taken a direct-sales motion from zero to $100M. Now, they’ve hit $200M ARR. Before Legora he spent seven years at Braze, from the early days through its path to IPO.
About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Lessons from building 113 AI agents and reinventing a GTM function with AI | Meagan (CMO, Samsara)
29 sept. 2026
00:43:45
The CMO of Samsara joins GTMnow to walk through exactly how she ran an AI transformation inside a public company, from a 2.5 week boot camp to 113 agents in production, all while keeping headcount flat and pushing pipeline and revenue up.
Meagan has led teams through platform shifts before (PLG, social, Covid) at MongoDB, DocuSign, Nieman, and now Samsara, and she argues AI is categorically different: not a new channel, but a production shift that changes how the work itself gets done. She gets tactical on the change-management sequence (learn by doing before you cap anything), how agents live in Slack for every function, the ABM pages that went from 2-3 weeks to under 30 minutes, the KPIs she tracks, how she interviews for AI fluency, and her message to anxious operators: this is a chance to leapfrog, not a threat.
What you'll learn:
Why AI is a production shift, not just a new channel, and what that changes about running a team
The change-management order that works: let people learn and play before you put cost caps on
Inside the 2.5-week AI boot camp (vibe-coded LMS, hands-on agent build, present-back) that trained half the org
Why she democratized agent-building into every function instead of centralizing an AI team
How 113 agents run in Slack across events, sales, ADR support, and creative
The rebrand that hit the market in 3.5 weeks instead of six months
ABM landing pages from 2-3 weeks to under 30 minutes, and content from weekly to 10 a day
How she keeps headcount flat: backfill differently, raise the bar on output
How she interviews for AI fluency, and why you can't earn a top calibration score without building agents
Her advice to anxious operators: build agents to leapfrog leadership, don't wait
Thank you to our sponsor: @NooksHQ - discover how revenue agents can transform your GTM at nooks.ai/gtmfund
About the guest: Meagan is the Chief Marketing Officer of Samsara, a public company on the NYSE. She has led marketing through major platform shifts at MongoDB, DocuSign, and Nieman, and has a background in MIS and computer science, starting her career as an IT engineer before moving into marketing.
About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Inside LinkedIn: buyer behavior, how to social sell, why warm intros get 3x the response, why only 45% of sellers are seen as trustworthy and the 4 behaviors that separate top sellers | Catherine Flynn (LinkedIn Sales Navigator)
23 sept. 2026
00:41:45
Information has never been more abundant, and trust has never been harder to earn. That's the tension at the heart of LinkedIn's new research, "The Trust Advantage," and Catherine, who leads marketing for LinkedIn's Sales Solutions business (Sales Navigator), joins Sophie Buonassisi on GTMnow to unpack it. The headline gap: 86% of B2B buyers say expertise is what builds trust, but only 45% describe the sellers they meet as trustworthy.
Catherine has spent 25+ years in marketing, including 13 at Meta, and now runs a global team out of Singapore. She argues AI has made "spray and pray" easier than ever, which is exactly why the winning move is doing less, more relevant outreach. She breaks down the four behaviors that separate top sellers, why warm introductions convert so much better, what a seller's LinkedIn profile should actually say, and how putting your expertise out publicly now helps both you and your company rank in AI search.
What you'll learn: - The trust gap: why 86% of buyers want expertise but only 45% find sellers trustworthy, and how to close it - Why expertise in a first conversation means leading with their problem, not your product - The case for less outreach: more signal means you can be far more selective - The four top-seller behaviors: signal-based selling, early multithreading, timely engagement (hours not weeks), and genuinely personalized outreach - Why warm intros win: ~3x higher email response and ~2x higher connection-acceptance than cold - The most underrated entry point: executive sponsors and former customers who moved companies - What a seller's LinkedIn profile should be (a point of view, not a resume), and why profile views are a top buying signal - The algorithm and discoverability: how posting even once a week, and engaging on others' posts, compounds - Why LinkedIn is now the most-cited domain for professional queries in AI search, and what that means for you - Hiring in the AI era: adaptability and generalists over specialists, and "throw your hat over the wall"
Connect with Catherine: LinkedIn: https://www.linkedin.com/in/catherineflynn/
Host: Sophie Buonassisi, SVP at GTMnow LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ X: https://x.com/sophiebuona
About the guest: Catherine leads marketing for LinkedIn's Sales Solutions business, home of Sales Navigator. She has 25+ years in marketing, including consumer and agency roots and roughly 13 years at Meta/Facebook, and is based in Singapore, where much of the Sales Solutions business is being built across APAC.
About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Why More AI Won't Grow Your Revenue (and What Will) | Loreal Lynch (CMO, Nooks)
15 sept. 2026
00:29:29
The CMO of Nooks (and former CMO of Jasper) joins GTMnow to explain why buying more agents won't grow revenue unless you rebuild the process underneath, and what the human-plus-agent revenue team truly looks like.
Loreal has had a front-row seat to two AI waves: first at Jasper, where AI reshaped marketing content, and now at Nooks, building toward what she calls the revenue agents category. She breaks down why the tools in today's GTM stack were built for humans to click through, not for agents to execute; why the org chart and the process both have to be rethought from the ground up; and why the real shift isn't reps prompting AI, but AI prompting reps. She also gets into the misconception that agents are easy to build, the CMO-CRO alignment model she runs with her counterpart Hannah, and why the marketing pendulum is swinging back from pure performance to brand.
What you'll learn: - Why bolting AI tools onto pre-AI processes fails, and what a real revenue operating system requires - The iceberg model of human vs. agent work, and why the waterline keeps rising - Why the future flips: AI stops waiting for prompts and starts prompting the rep - Augmentation over replacement: if an agent makes a rep 10x, you hire more reps, not fewer - The results some teams see: ~3x meetings booked and ~2x pipeline on the same headcount - Why "agents are easy to build" is a trap once you need shared data, governance, and calling/email infrastructure at scale - What stays human: judgment, narrative, and reading the room (the surf-small-talk story) - The CMO-CRO alignment model: shared pipeline goals instead of fighting over sourced-lead credit - Why marketing's pendulum is swinging back from performance to brand in the AI era - Why starting with a wedge (the dialer) and its conversational data beats selling a broad platform
Chapters: 00:00 Cold open: augmentation not replacement, and AI that prompts the rep 01:14 Welcome, and why she left Jasper's AI wave for Nooks 03:26 Seeing AI from every side: customer, board, now operator 04:27 The iceberg: human work above the water, agent work below 05:13 What humans do best vs. what agents do best 07:14 The real question isn't how many agents, it's who prompts whom 07:31 Augmentation over replacement: make a rep 10x, hire more 08:37 The results some teams see, and what's next 09:56 Why bolting AI onto old processes fails|12:06 The misconception that agents are easy to build 13:58 Going AI-native inside her own marketing org 15:10 The framework for what goes to headcount vs. agents 16:19 What stays human: judgment, context, and the naming story 17:32 CMO-CRO alignment: shared systems and shared metrics 19:43 How she and her CRO run pipeline without sourced-lead targets 21:40 What's changed, and what still works: the pendulum back to brand 23:42 What she's excited to build at Nooks 25:10 Who's winning with Nooks: the AI-native early adopters 27:06 Rapid fire: leadership, impact over activity, no time for bad wine 28:25 Who Nooks is hiring, and where to find Loreal
Connect with Loreal Lynch: LinkedIn: https://www.linkedin.com/in/lorealesque/
Host: Sophie Buonassisi, SVP at GTMnow LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ X: https://x.com/sophiebuona
About the guest: Loreal Lynch is the Chief Marketing Officer of Nooks, a revenue agents platform that started with an AI dialer and expanded across the sales engagement stack. She was previously CMO of Jasper, and earlier held marketing leadership roles at Salesforce, Tableau, and Stripe. Nooks' customers include Cursor, Replicate, Deel, and HubSpot.
About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Building an AI-Era Sales Machine | Chris McDonough (VP Sales, Campfire)
10 sept. 2026
00:42:28
Chris McDonough has joined four companies right before they exploded. At the first, Motive, he was employee 40 and watched revenue go from $800K to $30M in about 100 days. The VP of Sales at Campfire joins Sophie Buonassisi on GTMnow to break down what he learned riding hypergrowth over and over, and why he thinks AI is about to split the sales profession in two.
Chris gets tactical on the whole arc: how a two-week decision to sign a lease and move to SF changed his trajectory, what a federal mandate taught him about compelling events, why your career growth is tied directly to how fast your company grows, and how he now builds an AI-native sales org from scratch at Campfire (an AI-native ERP taking on the legacy giants). He also makes the contrarian case that AI won't replace reps but will widen the gap between them, why AI outbound is mostly spam for complex B2B, and why a strong SDR bench is existential.
What you'll learn:
The $800K-to-$30M-in-100-days story, and what a compelling event really looks like
Why your career trajectory is tied to your company's growth rate ("you can't be a VP if there's no one to be VP of")
The contrarian AI take: not labor replacement, but a top 30% worth triple and a bottom 20% that's hard to employ
What he hires for now: not just skill, but whether you can self-learn from AI on day one
How to build an AI-native sales org with no tech debt (the deal dashboard that grades every call against every win and loss)
Why AI outbound mostly becomes a spam tool in complex B2B, and why the SDR bench matters more
Why he leaves once a company is big enough to run Workday, and goes back downmarket
How to sell into the "real economy," where nobody cares about your hot VC and references are hyper-local
Regrettable churn: the retention metric behind Samsara's run, and why top reps compound
One-way vs. two-way doors: how to make fast decisions at 70-80% of the data
Chapters: 00:00 Intro 01:17 Welcome, and a career of joining companies right before they explode 01:51 Employee 40 at Motive, and the two-week decision that changed everything 04:19 The federal mandate, and the hiring class that got promoted in 30 days 05:33 Why career growth is tied to company growth rate 07:12 The mandate story: from selling nothing to 70 demos a week 10:19 Was it the wrong decision? Believing through the objection 10:56 What 800-900 demos in 3 months does to a seller 12:11 Samsara: scaling an office 0 to 100, and 250 interviews in 90 days 13:42 The contrarian hiring philosophy: the 10x seller and the widening gap 15:59 Why he left Verkada for Campfire, and the "Workday rule" 18:41 Building an AI-native sales org with no tech debt 21:14 What Campfire is: AI-native ERP and one of software's last moats 25:25 Expanding the TAM and the recession-proof case 26:12 Selling into the real economy: hyper-local references, not hot logos 28:26 His honest take on AI outbound and AI SDRs 30:49 The SDR org as your existential talent bench 31:56 The metric he obsesses over: regrettable churn 33:45 Who Campfire is hiring, and "will Claude kill this company?" 35:33 Rapid fire: leadership, execution over competitors, one-way vs. two-way doors 40:19 Where to find Chris, and how to actually DM your way into a job
About the guest: Chris McDonough is VP of Sales at Campfire, an AI-native ERP company competing with legacy incumbents like NetSuite. He was previously at Verkada, and earlier helped scale Motive (formerly KeepTruckin) from $800K to roughly $100M in revenue and Samsara through hyperscale, opening new-market offices in Nashville and Atlanta.
About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Inside Electric's AI Relaunch, from a 3X Founder | Ryan Denehy (Founder & CEO, Electric)
27 août 2026
00:45:23
The founder and CEO of Electric, Ryan Denehy joins GTMnow to explain why and how he rebuilt Electric as an AI-native software company.
Ryan gets specific on why he split the business in half, how the pivot forced a total change in distribution (from direct sales to embedded channel partnerships with payroll platforms), and why a new product doesn't just need a new channel, it can unlock ones that were impossible before.
He also shares the ADP partnership that put Electric behind 1,700 reps, the near-death moments (including the night he almost wired his seed round back to investors), how to actually get acquired by a public company, and the cold-outreach framework he's used since making extreme-sports videos at 17.
What you'll learn: - Why he rebuilt a working company AI-native, and the five-step playbook for a "total reinvention" - Why product-market fit is as much about distribution as the product, and the Sirius XM lesson behind it - How going AI-native collapsed his unit price and made channel-led growth possible for the first time - Why the winner-take-all gap between AI companies is so much wider than in classic SaaS - The embedded-partnership motion behind ADP, Justworks, and TriNet deals (300+ customers onboarded in a day) - How to actually get acquired by a public company (hint: people buy companies, corp dev doesn't) - Why the quietest near-death threat is a splashy senior mis-hire, not a market crash - The cold-outreach framework he's run since cold-emailing pro athletes at 17
Chapters: 00:00 Intro 01:04 A 3x founder who sold two companies to public acquirers 01:33 What Electric is, and why "AI" was in the name in 2016 04:40 What a "wholesale rewrite" meant 06:38 Why go AI-native 08:12 The reinvention playbook 13:08 Why they blew the whole thing up 13:48 Distribution as product-market fit: the Sirius XM lesson 15:37 How AI collapsed the price and unlocked channel sales 18:19 The winner-take-all gap between AI companies 20:35 From direct sales to channel 23:00 The three-year channel payoff 25:17 Rebuilding the product and signing the payroll platforms 26:27 The new-category pitch 29:29 Behind the scenes for ADP, Justworks, and TriNet 30:02 Almost wiring the seed money back 32:00 The day everything changed at once 33:52 The quiet damage of a senior mis-hire 35:48 Two prior companies: go-to-market above all 38:18 How to get acquired by a public company 42:55 Extreme-sports videos at 17, and the outreach framework 44:47 Where to find Ryan and Electric
Connect with Ryan Denehy: LinkedIn: https://www.linkedin.com/in/ryandenehy/ X: https://x.com/DenehyXXL Electric: https://electric.ai
Host: Sophie Buonassisi, SVP at GTMnow LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ X: https://x.com/sophiebuona
About the guest: Ryan Denehy is the founder and CEO of Electric, an AI-native IT management platform now embedded in payroll and HR products including ADP Team Management, Justworks, and TriNet. A three-time founder, he previously built and sold companies to USA Today and Groupon. Electric is backed by investors including Notable Capital and Slack.
About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
What the Top 1% of Sellers Do Differently | Ross Rich (CEO, Accord)
25 août 2026
00:51:53
Ross Rich is the co-founder and CEO of Accord and spent five years leading go-to-market and partnerships at Stripe. He talks to hundreds of CROs and serves thousands of reps, so he has an unusually clear view of what the top performers actually do differently.
His starting point: roughly the top 20%, often closer to 10%, of any sales team drives most of the revenue. Every leader says they want to move the middle 60%, and Ross doesn't think AI is doing it. Tools like Claude and Codex make the people who already have the taste and judgment far more efficient, and the gap widens from there. What closes it is unglamorous and human: a leader with a point of view, a shared language simple enough to stick, a field-friendly process, and only then the technology to reinforce it.
Ross gets specific on what "best" means for a seller (trust and EQ first, then frameworks learned so cold they run subconsciously), the disconnect between what CROs think they're buying and what reps actually receive, the "no-ask note" for multithreading into a CRO, why he sells through his own executives instead of around them, and the biggest lesson of his founder journey: market beats product.
What you'll learn: - What separates the top 10% of reps from everyone else, and why AI is widening that gap instead of closing it - The two ingredients of a great seller: the "give a shit factor" you can't fake, then plays run so subconsciously you can get creative - The waiter analogy that explains great salesmanship in one sentence - Why the people, process, technology order is the one most teams get backwards in the AI rush - The disconnect between a CRO's multimillion-dollar investment in the field and what reps actually receive: a 76-page laminate, more Salesforce fields, none of it touching the customer - Why the best methodology is simply the one that gets used, and why debating how many Ps are in MEDDPICC is optimizing the fringes - "Unavoidable excellence": how to take what your top performers do organically and make it standard across the team - The "no-ask note" for multithreading into a CRO by showing respect instead of asking for time - Why CROs own revenue and not tools, and how to sell through their rev-ops and enablement leaders - "Show, don't tell": leading with peer references at stage two when everyone can sound the same and ship a surface-level solution - The founder-led sales handoff mistake Ross has made twice, and the curse of knowledge behind it - Why market beats product, via April Dunford's positioning and the surfer, surfboard, wave framing
Connect with Ross Rich: LinkedIn: https://www.linkedin.com/in/rossrich/
Host: Sophie Buonassisi, SVP at GTMnow LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ X: https://x.com/sophiebuona
About the guest: Ross Rich is the founder and CEO of Accord, a platform that operationalizes value selling (quantified business cases, mutual action plans, stakeholder mapping, account planning) in a field-friendly way. Before founding Accord, he spent over five years at Stripe leading go-to-market and partnerships. Accord's customers include Freshworks and Samsara.
About GTMnow: GTMnow is the media arm of GTMfund, sharing how the best in tech build, scale and invest.
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Will Salesforce Win the AI Era Like It Won Cloud? | Kris Billmaier
11 août 2026
00:43:41
Is Salesforce the dominant player in the AI platform shift, or the incumbent about to be disrupted? Kris Billmaier, EVP and GM of Agentforce Sales and Growth Products, sat down with Sophie Buonassisi at Salesforce Tower to answer that directly.
Kris runs the business behind Sales Cloud's 26-year run and its rebrand into Agentforce Sales. He makes the case that CRM is becoming "agentic revenue orchestration," that the category needs a new name, and that the future is headless. For Salesforce, that means surfaced inside Slack, ChatGPT, Gemini, and wherever sellers actually work. He also shares the internal numbers, including an engagement agent that worked the leads Salesforce had always ignored and generated over $100M in pipeline in eight months.
What you'll learn: - Why 60% of a seller's time goes to non-selling work, and which agents remove it - The case for renaming the category from CRM to agentic revenue orchestration - What "headless CRM" means, and why Salesforce integrated with ChatGPT and Gemini - How one leader manages 100 reps plus the equivalent of 400 agents - Why the Momentum acquisition matters: "memory fragments" that cut an 8,000-word meeting to the 800 words that count - Why Salesforce is hiring more sellers, not fewer - How hiring shifted from "what did you do" to "how do you build" (and why a PowerPoint is now a red flag) - Pricing in the agent era: seats, flex credits, and a coming leads-worked outcome metric - Why Kris says we're not in a SaaSpocalypse, and how a 70,000-person company still ships weekly
Thank you to our sponsor: Primer unlocks B2C ad channels for B2B marketers with precision targeting and next-gen measurement. GTMnow Network exclusive offer: Extended 45 day trial and 15% off with code GTM15 - just apply the code when you go to upgrade from the free trial. See who’s really in your funnel: sayprimer.com
Chapters: 00:00 Intro 01:12 Welcome, and the Salesforce platform-shift question 02:25 How Salesforce adapted across cloud, mobile, social, and AI 03:32 Why Sales Cloud became Agentforce Sales 05:17 Renaming the category: from CRM to agentic revenue orchestration 06:56 Will anyone log into a CRM again? 08:09 Agentforce in one line, and the seller's Monday morning 09:08 Build vs. buy, vibe coding, and the context moat 11:01 The Momentum acquisition and memory fragments 13:04 Sellers managing teams of agents, and the $100M pipeline story 15:03 The agent stack: prospecting, engagement, pipeline, quoting 16:27 Efficiency, accuracy, and auto-generated forecasts 18:03 Why Salesforce is hiring more sellers 19:16 What the modern sales role looks like 20:08 Sponsor: Primer 21:34 How AI changed hiring: from "what" to "how" 23:48 The window: shipping weekly, not on three annual releases 25:13 What product-market fit means now 26:05 Software vs. services, and the $10T question 28:10 The complexity problem: easy by default, advanced by choice 30:07 Go-to-market evolution and consolidating the stack 32:07 Leading as a player-coach 33:16 Being "chief repetition officer" and educating the field 35:00 How a 70,000-person company stays agile 36:48 The biggest lesson from Marc Benioff 37:57 Pricing: seats, flex credits, and outcome-based metrics 40:53 Are we in a SaaSpocalypse? The full answer 42:08 Where Kris gets his learnings 43:07 World Cup picks
Kris Billmaier (EVP and GM of Agentforce Sales, Salesforce) LinkedIn: https://www.linkedin.com/in/krisbillmaier/ Salesforce Agentforce: https://www.salesforce.com/agentforce
Sophie Buonassisi (Host, SVP at GTMnow/GTMfund) LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ X: https://x.com/sophiebuona
About Kris Billmaier: Kris Billmaier is EVP and GM of Agentforce Sales and Growth Products at Salesforce, where he leads the business formerly known as Sales Cloud. He oversees the company's agentic sales portfolio, including its prospecting, engagement, pipeline, and quoting agents, and the Momentum acquisition that powers its conversational data layer.
About GTMnow: GTMnow shares how the best in tech build, scale and invest. The media brand is owned and operated by venture firm, GTMfund.
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Inside Deel's $1M → $1.5B Sales Machine | Chris Lee
03 août 2026
01:06:43
Chris Lee joined Deel at $1M in revenue. Now, it just hit $1.5B. He joined GTMnow to walk through the pivotal decisions behind that run, including the ones he's never discussed publicly.
Chris (Head of Sales, Americas at Deel) breaks down the "five-star sales experience" framework he built by studying luxury hotels, why speed itself became a reason customers bought, how he's had zero regrettable director-level attrition in 5.5 years, and why they hire people with the job title "Ghostbuster" to keep a 7,000-person company moving like a 30-person startup.
What you'll learn: - The five-star sales experience framework, and how to map your own process from three-star to five - Why every new sales leader at Deel spends their first 30 days taking inbound and selling - How speed became the reason Coinbase chose Deel over a legacy vendor with no references to show - The hire-slow, fire-fast principle behind zero regrettable director attrition in 5.5 years - Why "tell me about a time" interview questions optimize for the best liar, and the scenario-based alternative - What a "Ghostbuster" is, and how the role fights operational decay as you scale - Leading a sales team through public crisis: cry, quit, or fight - The trillion-dollar thesis: why 95% of the world's workers sit outside the US market - Why Chris went back to first-principles systems thinking instead of fiddling with AI tools
Thank you to our sponsor: Primer unlocks B2C ad channels for B2B marketers with precision targeting and next-gen measurement. GTMnow Network exclusive offer: Extended 45 day trial and 15% off with code GTM15 - just apply the code when you go to upgrade from the free trial. See who’s really in your funnel: sayprimer.com
Chapters: 00:00 Intro 00:58 Welcome to GTMnow 01:33 From Granular (agtech, employee #11) to a DuPont acquisition 05:30 The failed recruiting startup he launched in January 2020 07:17 How he found Deel, and applying to the wrong role on purpose 09:48 The first-30-days lesson from CEO Alex Bouazizi: go sell 11:44 What Deel actually does today 13:14 Scaling a distributed sales org remotely 15:41 Building rapport on a global remote team 17:35 From transactional SMB to multi-product enterprise 20:16 Sales-led, not product-led, and why consolidation wins 22:45 "Deel speed," and why speed is a reason people buy 25:31 Sponsor: Primer 26:57 Frank Slootman, Amp It Up, and outpacing competitors 29:12 How he got Slootman to open the sales kickoff 30:28 Zero director attrition in 5.5 years, and hire slow, fire fast 33:54 Why "tell me about a time" fails, and the scenario-based alternative 37:46 The five-star sales experience framework 41:54 Bringing enterprise-grade experience to SMB with AI 45:49 The trillion-dollar thesis: 95% of workers are outside the US 47:22 Building 60+ payroll engines: the Amazon Prime parallel 53:02 First-principles systems thinking for sales 59:38 The problem-framing framework he gives his team 01:01:09 The "Ghostbuster" role and fighting operational decay 01:05:25 Where to find Chris
Chris Lee (Head of Sales, Americas at Deel): LinkedIn: https://www.linkedin.com/in/techcontrarian/ X: https://x.com/TechContrarian
Sophie Buonassisi (Host, SVP at GTMnow/GTMfund): LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ X: https://x.com/sophiebuona
About Chris Lee: Chris Lee is Head of Sales, Americas at Deel, which he joined as one of its first sales hires at $1M in revenue and helped scale to $1.5B. Previously he was employee number 11 at Granular, an agricultural tech company acquired by DuPont for $300M.
About GTMnow: GTMnow shares how the best in tech build, scale and invest. The media brand is owned and operated by venture firm, GTMnow is the media arm of GTMfund.
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Inside Merge: The $75M Bet on Open Source AI (Powering OpenAI, Netflix & Uber) | Shensi Ding, CEO
22 juil. 2026
00:47:18
The Co-Founder & CEO of Merge joins GTMnow to break down how she built a company that now powers integrations for OpenAI, Perplexity, Netflix, Uber, Mistral, and enterprise logos like Mastercard, JP Morgan, and Amex, backed by $75M from Accel and NEA.
Shensi gets tactical on the GTM decisions behind that growth: why she went enterprise-first into greenfield, why she's now layering a self-serve motion back on top (20,000+ self-serve orgs, 400+ enterprise customers), how forward-deployed engineers turned a 1% edge case into 5 to 10x usage growth, and why she rebuilt marketing to run like an engineering team. She also gets candid on founder-led sales, the mercenaries-versus-missionaries hiring trap, the open-source model shift and the China question, and why every founder who started pre-AI should build one product 0-to-1 themselves.
What you'll learn: - Why she reversed the standard GTM playbook (enterprise first, then PLG) and how to run both motions at once - How forward-deployed engineers close the 1% edge case that unlocks 5 to 10x enterprise usage - Why marketing now runs like an engineering function at Merge, and how it took her from 1 to 2 dinners a quarter to 3 to 5 a month - Why product got fast and go-to-market became the new bottleneck - How to know when to hire your first salesperson (hint: you should be "dying" first) - The mercenaries-vs-missionaries test, and the "anti-sell" she uses in hiring - The 2026 shift away from "token-maxing," and how model routing cuts AI spend - The truth about open-source (often Chinese) models: where they're built vs. where your data actually lives - Why founders who started pre-AI should build one product 0-to-1 to understand what's now possible
Chapters: 00:00 Intro 01:14 What Merge does: products, workforce, and three core offerings 02:05 Agent Handler, Gateway, and the new Embedded Routing Stack 04:52 The 2026 shift away from "token-maxing" 07:29 Open-source models, the China question, and where data really lives 10:14 How Merge works with open-source model providers 12:00 What she's learned as a first-time founder: get over your ego 13:22 Reversing the GTM playbook: enterprise-first, then PLG 15:50 Running both motions: 20,000+ self-serve, 400+ enterprise 17:31 Why buyer behavior moved to Twitter and brand 19:06 Founder-led sales, and what a real sales process taught her 22:27 When to hire your first salesperson 23:49 Forward-deployed engineers and 5 to 10x usage growth 27:00 Keeping go-to-market up to speed with product 28:33 Rebuilding marketing as an engineering function 30:45 The dinner agent: 1 to 2 a quarter to 3 to 5 a month 31:24 How AI buying reshaped the marketing org 33:54 Maintaining agents: prompts over legacy builders 35:02 Mercenaries vs. missionaries, and the "anti-sell" 40:25 The market view: from hostility to collaboration 42:06 Is a valuation reckoning coming? 43:07 Why she stayed hands-on building Agent Handler and Gateway 45:18 What's next: training your own models off open-source 46:52 Where to find Shensi and Merge
Connect with Shensi Ding: LinkedIn: https://www.linkedin.com/in/shensiding/ X: https://x.com/shensi Merge: https://merge.dev
Host: Sophie Buonassisi, SVP at GTMnow LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ X: https://x.com/sophiebuona
About the guest: Shensi Ding is the co-founder and CEO of Merge, a unified API platform that now spans product integrations, agent tooling, and LLM routing/governance. Merge powers companies including OpenAI, Perplexity, Netflix, Uber, and Mistral, and enterprise customers like Mastercard, JP Morgan, and Amex. The company has raised $75M from Accel and NEA.
Thank you to our sponsor:
Primer unlocks B2C ad channels for B2B marketers with precision targeting and next-gen measurement. GTMnow Network exclusive offer: Extended 45 day trial and 15% off with code GTM15 - just apply the code when you go to upgrade from the free trial.
About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
The Blueprint for a High-Performing Sales Team | Brian Le, Notion
09 juil. 2026
00:45:54
Are your sales compensation plans driving the right behaviors or causing your best reps to quit? In this episode of GTMnow, Brian Le (Global Sales Compensation Partner at Notion) breaks down how to build a scalable sales comp operating system.
Brian shares his firsthand experience scaling Notion's sales comp from 80 to over 400 employees and explains why trust is the ultimate currency in revenue operations. If you are a founder, revenue leader, or sales professional, this breakdown covers everything from structuring pay mix to identifying the earliest signs of comp plan degradation. You will even hear what it takes for top AEs to pull in upwards of $1 million in a single quarter.
In this episode, we cover: 00:00 Intro 01:15 Brian Le's journey through Salesforce, Carta, and Notion 04:33 Why sales comp is the operating system for go-to-market 07:07 Phase 1: Building a scalable comp foundation at Notion 13:50 Transitioning from seat-based to usage-based pricing models 18:15 The 3 core pillars of a successful sales commission plan 22:09 Early warning signs your quota and comp structures are breaking 31:41 The real cost of losing sales reps over bad commission payouts 39:35 How to structure compensation for your first early-stage sales hires 42:39 Will AI agents replace SDRs and sales compensation?
Connect with Brian Le, : LinkedIn: https://www.linkedin.com/in/brianhoangle/
Host: Sophie Buonassisi, SVP at GTMnow LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ X: https://x.com/sophiebuona
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
VC: How a 2-Person Fund Runs Like a Startup (Memos, KPIs, R&D) | Vanessa Larco, Premise (ex-NEA)
08 juil. 2026
00:48:50
"Investing in companies that OpenAI won't kill." That's Vanessa Larco's thesis, and in this VC bonus episode of GTMnow she breaks down exactly how she decides what survives. Vanessa, founder and GP at Premise (formerly a longtime partner at NEA, where she backed Robinhood from seed to IPO), joins Max to get into the nitty gritty of how AI is rewriting venture, distribution, and the entire go-to-market playbook.
She makes the case for why "it's just a wrapper" got a lot of VCs in trouble, why she only backs technical founding teams, and why the old GTM playbook is breaking fastest exactly where you'd least expect it. She also opens up about leaving a big platform to build a two-person fund from a blank canvas, and why she treats the fund itself like a startup.
What you'll learn: - The "OpenAI won't kill it" framework for spotting durable AI companies (and why not everything OpenAI ships actually wins) - Why the "it's just a wrapper" dismissal cost VCs real deals, and the kayak/AWS parallels that explain why - Why Premise only backs technical founding teams, and the shipping speed that becomes the real early moat - How the old go-to-market playbook is breaking, especially in DevTools, and what replaces it - Why someone on the founding team has to "nerd out" on distribution, and why no-playbook moments are where you growth hack - How to run a conviction-based investment committee, and why big funds drift toward consensus whether they like it or not - Why running a fund is just running a startup: fundraising, product, and customer success by another name - The unanswered question Vanessa keeps circling: how to give experienced GTM talent space to rewrite the playbook
Chapters:
00:00 Intro & OpenAI Moats 01:12 GTMnow Intro 01:51 Technical vs. Non-Technical AI Founders 04:37 The Bottleneck of Hiring AI Talent 05:15 Do Old Moats Still Exist? 06:36 Cloud Era Lessons vs. Today's AI Layer 09:18 The Shift to the Distribution Era 11:38 Interview: Vanessa Larco (Premise VC) 12:40 Companies OpenAI Won't Kill 13:37 Consumer Habits vs. Enterprise AI 15:05 Moving Beyond the "Wrapper" Stigma 17:39 Thesis Building vs. Founder Curiosities 20:11 Sourcing & The "Surreal" Community 22:26 Learnings From NEA & Lightspeed 24:06 Rethinking the Investment Memo 26:43 Consensus vs. Conviction Investing 31:26 Running a VC Fund Like a Startup 35:04 Building Internal Automation Tools 37:35 Distribution Moats & DevTools 39:38 Sourcing New GTM Playbooks 41:12 Parallel to the AWS Boom 43:55 Human Psychology vs. AI Tools 47:06 SF's Best Cookie Spots 48:32 Outro
Connect with Vanessa Larco: About the guest: Vanessa Larco is the founder and GP at Premise. Previously a partner at NEA, she backed consumer and fintech companies including Robinhood from seed through IPO. She started her career in product and engineering, was a computer science undergrad, and founded and sold her own startup before moving into venture.
Connect with Max: https://x.com/hackitmax https://www.linkedin.com/in/maxaltschuler/
Connect with Vanessa: https://www.linkedin.com/in/vanessalarco/ https://x.com/veelarco
About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market. This is the VC bonus series, where we host VCs and get into the VC ecosystem.
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Why a $1.2B exit felt like his biggest failure, and the customer-obsession thesis behind Agency
02 juil. 2026
00:52:51
A $1.2 billion exit is the dream. Elias Torres calls it his biggest failure. The Drift co-founder joins Sophie Buonassisi on GTMnow to unpack why the headline number felt hollow, what he learned in the quiet stretch afterward, and why he jumped straight back in to build Agency, an AI company that runs your entire customer organization.
Elias gets honest about identity after the exit, the difference between chasing a title and building something enduring, and the operating thesis behind Agency: a billion-dollar company with fewer than 100 people, where 80 to 90% of the team are engineers and everyone talks to customers. He also gets into distribution as the hardest problem in the AI era, why he only takes money from investors who lead with value (Pat Grady and Brian Halligan back the company), and the two decades he's spent building alongside David Cancel.
What you'll learn: - Why a $1.2B exit can still feel like a failure, and what "enduring" actually means - How to rebuild your identity when the title goes away - The Agency thesis: $1B with under 100 people, and how AI agents make it possible - Why Elias runs the whole company on Agency itself, with no CRM - Why sales may be the last role AI eliminates, and what that means for GTM - How to spot investors who lead with value instead of a pitch deck - Why distribution, not product, is the hardest problem in the AI era - What 20+ years building with David Cancel (Performable, HubSpot, Drift) taught him about partnership
Chapters: 00:00 Intro 02:25 Time off, slowing down, and losing the title 04:00 The inflection point and what comes after a big exit 07:00 What Agency is and the problem it solves 11:00 Why he brought people he's known for years 11:40 Investors who lead with value (Pat Grady and Brian Halligan) 17:30 Building with David Cancel for 20+ years 23:00 The bold claim: $1B with under 100 people 26:00 The go-to-market motion behind it 28:30 "Sales is the last role AI will eliminate" 36:00 High-agency people and how Agency runs itself 42:00 Building distribution in the AI era 51:00 Where to find Elias and Agency
About the guest: Elias Torres is the founder and CEO of Agency, an AI company that provides agents to run a company's customer organization. He previously co-founded Drift (acquired in a $1.2B deal) and held senior roles at HubSpot and Performable, building alongside David Cancel for over two decades. Agency is backed by Pat Grady (Sequoia) and Brian Halligan.
Connect with Elias Torres: LinkedIn: https://www.linkedin.com/in/eliast/ X: https://x.com/eliast
Host: Sophie Buonassisi, SVP at GTMnow LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ X: https://x.com/sophiebuona
About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
From DeepMind to 200 Customers in 20 Countries: Building the Execution Layer for Sales | Adam Liska, CEO of Airspeed
25 juin 2026
00:32:22
The single most expensive sentence in sales is "I'll follow up on that." Adam Liska joins Sophie Buonassisi on GTMnow to break down the "execution gap," the space between knowing what to do in a deal and actually doing it, and why that gap is where most pipeline quietly dies.
Adam left DeepMind's Gemini team in 2022, pre-ChatGPT, to build a native revenue execution platform now serving 200 customers across 20 countries (recently rebranded and fresh off a $20M Series A). In this conversation, he gets specific on what is actually changing in the sales role, what should be automated, and why he thinks this is about to be the golden age for sales reps.
What you'll learn: - Why "I'll follow up on that" is the most expensive promise in revenue, and how the execution gap compounds from rep to manager to CRO - What parts of the rep workflow to automate now (research, CRM updates, business cases, follow-ups) and what stays human - Why AI is squeezing middle management, not reps, and flattening GTM orgs - How per-rep coaching changes when every call is recorded, shared, and analyzed for patterns - The "corrective action" approach to coaching deals on the job, in real time - How to sell globally when borders disappear but local-language talent still matters - Why in-person events drove 70% of early pipeline, and how that compounds with cold calling - How to keep your team at the AI frontier by never locking into a single model - Adam's #1 piece of advice for first-time founders (hint: it starts with your co-founder)
Chapters: 00:00 Why AI won't replace sales reps 00:22 Leaving DeepMind's Gemini team pre-ChatGPT 01:18 What airspeed does and the "execution gap" 02:07 "I'll follow up on that": the most expensive promise in sales 03:28 The $20M Series A and the rebrand from Glyphic 05:30 Why walk away from frontier AI research at DeepMind 07:17 Leading when the frontier models keep changing 08:39 Buy vs. build, and keeping customers at the AI frontier 11:03 Landing the first 200 customers across 20 countries 12:41 Advice for first-time founders 14:04 Selling globally and what AI changes about language 17:07 What the sales rep role looks like in an AI-first world 19:24 How reps and leaders should start automating today 20:51 The channels driving results right now 22:41 How AI makes per-rep coaching actually work 25:14 Building an execution-first culture 27:10 The DeepMind departure story 28:51 Building in London vs. selling in the US 30:43 Adam's favorite AI use case as a busy CEO 31:26 The biggest misconception about AI in sales
Host: Sophie Buonassisi, SVP at GTMnow LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ X: https://x.com/sophiebuona
Guest: Adam Liska, Co-founder and CEO at Airspeed X: https://x.com/adliska LinkedIn: https://www.linkedin.com/in/adliska/
About the guest: Adam is the co-founder and CEO of Airspeed (formerly glyph), a native revenue execution platform that closes the gap between knowing what to do in a deal and executing on it. Before founding the company, he worked at DeepMind on the team that became Gemini.
About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
VC: How Benchmark Picks AI Winners - Max 10 Bets a Year, 5 Partners | Chetan Puttagunta (GP)
24 juin 2026
00:59:24
Benchmark's Chetan breaks down why the path from $0 to $100M has collapsed from five years to under two, and the one thing that is actually getting harder in the AI era: reaching your first million in revenue. In this VC bonus edition of the GTM Now Podcast, he sits down with Sophie Buonassisi to unpack how AI native companies are compressing 180 day sales cycles into 30 days, why direct sales is here to stay, and how value is shifting away from code toward the last mile of customer service.
Using Legora (legal AI) and Manus as case studies, Chetan explains how Benchmark builds conviction fast, why the marginal cost of code trending to zero changes everything, and what separates the founders who win this window from the ones who miss it.
What you'll learn: - Why the first $1M now takes longer than the next $99M in the AI era - How top AI startups compress a 180 day sales cycle into 30 days - The "trusted vendor" playbook for breaking incumbent distribution advantages - Why Legora embedded inside a law firm for a year before launching - How a magical demo plus a tightly scoped pilot collapses six month deals - Why value is moving from the product build to the service and outcome - What Benchmark actually looks for: technical insight that creates demand pull - Why direct sales and forward deployed engineers are exploding in AI - How buying one AI app triggers an enterprise to buy 100 more
Chapters: 00:00 Intro 01:13 Why Max + Paul were furious taking notes on this one 02:10 Benchmark's $2B growth fund and the changing strategy 04:57 POC to trial and the power of direct sales in AI 11:33 Meeting Max early: $0 to $100M in 18 months 15:05 Manus: 0 to $100M in eight months through PLG 17:10 Will the AI native window close? 19:09 Sizing the window: $40B software vs $1T services in legal 21:50 How Benchmark picks the winners 25:31 Turning a 180 day sales cycle into 30 days 30:45 The Legora deep dive: research, pilots, legal engineers 41:46 Why $0 to $100M keeps getting faster 42:29 The harder problem: getting to your first $1M 44:04 When code goes to zero, what do customers pay for? 48:46 Sales led vs PLG in the AI era 51:49 How to spot the right founder 55:18 What company Chetan wishes someone would build 56:48 Investors founders should follow 57:40 Working with Jack Altman at Benchmark
Connect with Chetan Puttagunta: General Partner at Benchmark Twitter/X: https://x.com/chetanp LinkedIn: https://www.linkedin.com/in/chetanputtagunta/
Host: Sophie Buonassisi, SVP at GTMnow Follow Sophie: https://x.com/sophiebuona LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
About the GTMnow Podcast: GTMnow is the media brand of GTMfund, sharing the tactics and strategies behind how the best companies go to market. The VC series brings on top investors to break down what is actually working in go to market today.
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Ads in ChatGPT Are Coming. What B2B Marketers Should Do Right Now | Keith Delaney, CEO Primer
17 juin 2026
00:45:43
LinkedIn CPMs just hit $800. AI is flooding every channel with content. Outbound is dying. So where should B2B marketers actually spend their ad budget right now?
Keith Putnam-Delaney, co-founder & CEO of Primer, joins Sophie to break down the complete state of B2B paid advertising, what's broken, what's working, and where the real opportunities are hiding in 2025.
What you'll learn: - Why LinkedIn & Google search are hitting a ceiling (and what to do instead) - How to get 80% match rates on Meta and 70% on Reddit for B2B audiences - The only moat competitors can't copy: your targeting - Why you need to feed CRM conversion data back to ad platforms - Holdout groups, attribution, and what actually proves paid ROI - The truth about ads in LLMs (ChatGPT, Perplexity, Grok) - B2B influencer marketing: the most undervalued tactic right now - Founder lessons from 6 years and 3 pivots building Primer
Chapters: 0:00 – The paid advertising crisis no one's talking about 2:40 – AI's real impact on ad costs 4:06 – Google Search & AI Overviews: what still works 5:04 – LinkedIn CPMs: $20 to $800 in 18 months 6:39 – Why B2B brands need to be on Meta, Reddit & Instagram 7:01 – What Primer does (80% match rates explained) 9:29 – The device fragmentation problem & attribution 11:16 – Holdout groups: the statistically proven approach 13:30 – Which channel to start with (and minimum spend) 22:18 – Paid ad creative: feed the algorithm with variants 25:14 – B2B influencer marketing & thought leadership ads 30:59 – Why you MUST push CRM data back into ad platforms 33:31 – Ads in ChatGPT & LLMs: what's coming 35:53 – Founder lessons, mental health & iteration
Connect with Keith Putnam-Delaney: Co-founder, CEO of Primer Twitter/X: https://x.com/kcpdelaney LinkedIn: https://www.linkedin.com/in/keithputnamdelaney/
Host: Sophie Buonassisi, SVP at GTMnow Follow Sophie: https://x.com/sophiebuona LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
About Keith Putnam-Delaney: Keith is the co-founder and CEO of Primer (https://www.sayprimer.com/), a B2B paid advertising targeting layer that helps brands unlock high match rates on Meta, Google, Reddit, and beyond. Former brand marketer turned data-driven growth leader.
GTMnow is the media brand of GTMfund, sharing go-to-market insights from the top 1% of revenue operators.
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
He's Seen 300+ Sales Comp Plans. 90% Make the Same Mistake | Siva Rajamani (Everstage CEO)
15 juin 2026
00:57:22
Most sales comp plans are quietly broken, and the people running them have no idea. Siva Rajamani, CEO of Everstage, has visibility into 300+ enterprise comp plans, and he says 90% of companies make the same mistakes. In this episode he breaks down what's going wrong, how to spot it, and what a comp plan that actually drives revenue looks like.
Siva explains why sales compensation is not a back office cost center but the single biggest lever in your go-to-market strategy. It's the glue between what a company intends and what reps actually do. If your reps aren't doing what you want, the answer isn't in a 1-on-1. It's in your comp plan.
We get into the over-complication trap, the hidden math that makes reps refuse your best deals, the base-to-variable ratios that actually work, why your top reps should out-earn almost everyone, and how AI is about to blow open the gap between your best and average sellers.
Chapters: 00:00 Intro 00:30 Siva's RevOps background at Freshworks 04:00 Scaling RevOps from 1 to 25 04:50 Why he left to build Everstage 06:30 Why incentives drive revenue, not tools 08:00 Comp as the glue between intent and action 10:30 The 1 to 2 mistakes almost every team makes 12:00 "If your comp plan needs FAQs, it's a tax code" 14:00 The 60-second test for a broken plan 15:30 Designing comp to retain top talent 16:50 How AI widens the gap between top and average reps 18:00 The $1M sales rep is coming 19:30 Why optimizing for top earners is better on margins 21:30 Quota to OTE ratios that actually work 23:00 Base vs variable: the 50/50 rule and exceptions 24:00 What Everstage does and who it serves 25:30 How Everstage structures its own comp plan 28:00 The rise of the revenue architect 48:00 CPQ and connecting margin to commissions 50:30 When should reps earn commission in the deal cycle 52:30 Six month vs twelve month comp cycles 54:30 The most a sales rep has ever made 55:20 Where to find Siva
Connect with Siva Rajamani: Co-founder, CEO of Everstage Twitter/X: https://x.com/siva_rajamani LinkedIn: https://www.linkedin.com/in/sivasrajamani/
Host: Sophie Buonassisi, SVP at GTMnow Follow Sophie: https://x.com/sophiebuona LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
ABOUT GTMnow
GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
Subscribe for more conversations with the operators and founders behind today's best go-to-market teams.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
"We Don't Fund Good Companies" : A $1.5B VC Explains Why | Ben Lerer, Lerer Hippeau
09 juin 2026
00:55:46
Ben Lerer, Managing Partner and Founder of Lerer Hippeau, has built one of New York's most influential early-stage venture firms across nine funds and nearly $1.5B in AUM. In this VC edition of the GTMnow podcast, Ben sits down with Max and Paul to unpack how he actually picks founders, why he wants to be the "worst investor" at his own fund, and the contrarian belief that backing good, sensible businesses is a mistake.
Ben got his start in media, building Thrillist before it merged into Group Nine, then turned those relationships and that operator empathy into a venture career writing early checks into companies like Warby Parker and Casper. He shares what's changed about winning deals in a more competitive, sharp-elbowed market, how Lerer Hippeau runs its investment committee on conviction rather than consensus, and the process failure behind passing on Peloton.
We also get into the debate every investor is wrestling with right now: the crazy, fast-moving AI-native founder versus the second or third-time operator with deep domain expertise, and why the answer is rarely a silver bullet.
A real venture-nerd conversation on firm building, IC decision-making, founder selection, and what it takes to chase the power law.
Topics covered: - The "worst investor at my own fund" philosophy - Conviction vs. consensus in the investment committee - Why Lerer Hippeau funds "crazy" founders, not good companies - The Peloton miss and what it revealed about process - From Thrillist and digital media to venture capital - AI-native founders vs. domain experts - How to win competitive deals as a smaller firm
Chapters: 00:00 Intro 00:52 Max and Paul on the episode: IC process and founder selection 14:36 Conversation with Ben Lerer begins 15:02 Nine funds, $1.5B AUM, and the early-stage strategy 23:00 From Thrillist to venture: the media springboard 28:00 What's changed in picking founders and winning deals 33:00 How the investment committee grew and evolved 37:40 The "magic" deal and chasing high-conviction bets 50:43 Why Ben wants to be the worst investor at his fund 53:00 Funding crazy people, not good companies 51:35 Yankees or Mets?
Connect with Ben Lerer: https://x.com/BenjLerer LinkedIn: https://www.linkedin.com/in/benlerer/
Connect with Max: https://x.com/hackitmax linkedin.com/in/maxaltschuler
Listen on Apple and Spotify, and subscribe for more GTMnow VC editions.
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
How Esper Is Building the Operating System for Government Policy | Maleka Momand
04 juin 2026
00:31:09
Maleka Momand, co-founder and CEO of Esper, joins Sophie Buonassisi on GTMnow to break down what it actually takes to build and sell software to government. Esper is the operating system for government policy, serving as the system of record for the regulation and internal policy that shapes daily life, from NYPD procedures to nurse practitioner licensing in rural Tennessee.
Maleka shares hard-won lessons from 8 years in GovTech: why winning trust matters more than winning business, why professional services are a moat (not a cost center), and how Esper turns slow, paper-based policy processes into live digital workflows. She also covers the DOGE effect across red and blue states, why enterprise SaaS still has defensible moats in the age of AI, and her advice to founders entering regulated markets.
Whether you're a founder, GTM leader, or operator selling into complex, slow-moving markets, this conversation is packed with practical playbooks on trust, go-to-market, and building durable enterprise software.
Chapters: 00:00 Intro 00:44 Two types of government policy (regulation vs internal) 02:06 The NYPD 3,000-page policy problem 03:23 Digitizing a paper-based, 20-person workflow 04:12 Why policy is infrastructure 05:23 Real impact: Tennessee healthcare & Arkansas hunting licenses 07:45 Esper's ideal customer: complexity, catalyst, volume 08:18 Going to market in GovTech (and why it's slow) 10:16 Advice for founders entering GovTech: win trust first 11:27 Why professional services are a moat 12:38 In-house vs third-party services 13:49 What DOGE actually looks like on the ground 15:11 Is DOGE a tailwind for Esper? 16:36 The new funding round & enterprise SaaS in the age of AI 19:13 From VC to founder: why Maleka made the shift 22:10 Advice for founders: read fiction, not productivity books 24:14 AI, data quality, and the problem with vibe coding 26:43 How Esper uses AI internally (meet "Poly") 27:27 Building a high-agency culture while scaling 29:00 Closing thoughts
Connect with Maleka Momand: Co-founder, CEO of Esper Twitter/X: @MalekaMomand LinkedIn: linkedin.com/in/malekamomand
Host: Sophie Buonassisi, SVP at GTMnow Follow Sophie: https://x.com/sophiebuona LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
ABOUT GTMnow
GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
Subscribe to GTMnow for the latest episodes on AI, founder strategy, fundraising, and go-to-market from the best builders in tech.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
How He Built a $250M Company With Zero Employees | Ben Cera, Polsia
29 mai 2026
00:50:44
One Person, $10M+ ARR, $30M Raised: How Ben Cera Built Polsia (AI Operating System) Solo
Ben Cera, founder of Polsia, just raised $30M at a $250M valuation while running the entire company alone. His AI agent handles his emails, manages customer support, even led his fundraising calls. This is what a solo founder with an AI operating system looks like at scale.
Polsia is an AI operating system that builds and runs companies autonomously. Give it an idea and it builds the product, writes code, conducts research, creates tweets, sets up company infrastructure, and works 24/7 on your behalf. Users are hitting $10M+ ARR using Polsia to scale their businesses.
In this episode we cover: 00:00 - Intro & The Viral Launch Nobody Forgot 01:24 - How He Raised $30M at $250M Valuation with Himself as the Only Employee 02:15 - The Origin Story: Building Polsia from Scratch 04:13 - Why the Controversial Product Name Became Free Marketing ($Millions in Earned Media) 05:55 - What Polsia Actually Does (AI Operating System for Founders) 06:25 - How He Hit $10M+ ARR Running Solo (No Cofounders, No Hires) 10:30 - Building a Company OS That Works 24/7 on Your Behalf 12:00 - The Psychology of Single Founder Mode (Why It Scales Faster) 14:45 - AI Agents Handling Customer Support, Refunds, & Bug Fixes 16:30 - Email Automation: How Polsia Responds to 100% of His Emails 20:15 - The Viral Fundraising Stunt (Live Dashboard + Agent-Led Investor Calls) 25:00 - Why He Let His AI Agent Handle First Meetings with Investors 28:30 - The Self-Fulfilling Prophecy of Distribution (More Visibility = More Traction) 32:15 - How Distribution Strategy Becomes Your Go-To-Market 35:45 - Building in Public While Running Everything Solo 38:00 - Customer Obsession at Scale (Staying Close When You're Alone) 42:56 - Founder Availability: Direct Phone Access to Customers 44:00 - Manufactured Moments That Feel Authentic 50:13 - Why Distribution Isn't an Afterthought Anymore
Key Insights: - One founder + AI operating system beats small teams without leverage (speed, decision-making, equity concentration) - Polsia lets you build multiple products simultaneously without hiring (products work 24/7 on your behalf) - The more controversial your positioning, the more people talk (free marketing from debate) - AI agents can handle 80% of founder work: emails, support, customer refunds, even investor screening - Live dashboards showing real-time growth create self-fulfilling prophecies (transparency = conviction) - Distribution is how you reach product-market fit faster (not an afterthought) - AI agents leading first investor meetings works (validates the product claim + generates buzz) - Customer intimacy at scale = founder still takes direct texts from users - Retention matters more than naming: customers don't complain about the name, they just use it - One person with AI tools > 5 people building without leverage
Why This Matters: This is the playbook for next-generation founders in 2026. Ben shows you how to: scale solo using AI agents, multiply your output without hiring, go viral intentionally, raise capital through distribution, and stay close to customers at scale. If you're a founder thinking about AI leverage, autonomous systems, or scaling lean, this is essential.
Watch This If You're: - Solo founders scaling without a team - Founders interested in AI agents and autonomous systems - Learning about AI-first product development - Studying modern GTM and distribution strategy - Raising capital in 2026 (fundraising case study) - Building products with AI agents doing the work - Curious about the solo founder + AI agent trend - Following autonomous company builders
Connect with Ben Cera: Founder & CEO of Polsia Twitter/X: @bencera LinkedIn: https://www.linkedin.com/in/benbroca/
Host: Sophie Buonassisi, SVP at GTMnow Follow Sophie: https://x.com/sophiebuona LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
ABOUT GTMnow GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
Subscribe to GTMnow for the latest episodes on AI, founder strategy, fundraising, and go-to-market from the best builders in tech.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
The $575B AI Bet (Biggest Since the World Wars) and the New Two-Buyer Reality in Software | Tomasz Tunguz, Theory Ventures
26 mai 2026
00:34:58
AI Infrastructure Spending is Insane: Hyperscalers Betting $575B on the Data Center Race | Tomasz Tunguz
This year's data center infrastructure spending will be the 5th largest infrastructure project in history (bigger than everything except railroads and the two world wars). Tomasz Tunguz breaks down what nobody appreciates about the scale of the AI boom.
Tomasz Tunguz, General Partner at Theory Ventures, and one of the most insightful voices on AI infrastructure, data stacks, and founder strategy.
In this episode we cover: 00:00 - Intro & The Scale Nobody Anticipated 02:13 - Data Center CapEx Could Hit 5-7% of US GDP by 2030 05:21 - For Every $1 AI Companies Make, They Spend $12 on Infrastructure ($575B Bet) 06:20 - Market Share Capture vs. Margin Games: The Chicken Game Big Tech is Playing 09:48 - How the Data Stack & AI/ML Worlds Have Completely Fused 12:33 - Product-Market Fit is No Longer Binary: It's Continuous Now 15:17 - How AI is Changing Venture Capital & Portfolio Management 17:09 - The Future: Image & Video Data is Going to Require MASSIVE Infrastructure 18:25 - Pattern Recognition Across Winning Companies (Domain Expertise is Key) 20:50 - Hot Take: Corporate Org Structure Will Transform in 5 Years 21:00 - Final Advice to Founders: Nobody Knows the Answer
Key Insights: - Hyperscalers are spending ALL free cash flow + borrowing heavily to fund data center CapEx (Meta, Google, Oracle levered 7:1 on cash flow basis) - The dominant metric: intelligence per watt of electricity - Anthropic rumored to have very high gross margins (first wave competition) - Data teams are now reporting to heads of engineering (huge organizational shift) - Inference demand is infinite: models are growing 5-10x in size - Foundation models broke product-market fit: it's now continuous, not static - Second-time founders win because they understand domain history & distribution - PR is now a major distribution channel for AI companies (unlike software era) - Building for images & video is the next frontier (1,000-10,000x larger than text data)
Watch this if you're: - Founders building AI/data companies - Investors analyzing the AI infrastructure play - Product leaders understanding AI's organizational impact - Anyone following the AI market seriously
Connect with Max: https://x.com/hackitmax https://www.linkedin.com/in/maxaltschuler/
Connect with Paul: https://x.com/PaulGTM https://www.linkedin.com/in/paulsirving/
Guest: Tomasz Tunguz, General Partner https://www.linkedin.com/in/tomasztunguz/ https://x.com/ttunguz
Host: Sophie Buonassisi, SVP at GTMnow https://www.linkedin.com/in/sophiebuonassisi/ https://x.com/sophiebuona
ABOUT GTMnow GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
Brought to you by: AngelList From starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure allowed us to scale without sacrificing agility, from onboarding hundreds of LPs seamlessly to handling compliance, capital calls, and reporting as our fund size evolved.
Transcript available under the episode here: https://gtmnow.com/tag/podcast/
Subscribe to GTMnow for the latest episodes! https://gtmnow.com
For inquiries about sponsoring the podcast, email gtmnow@gtmfund.com
GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
SEO Is Not Enough Anymore: Webflow's CEO on the Rise of AEO | Linda Tong
20 mai 2026
00:24:34
The future of websites isn't a builder problem anymore. It's an agent problem.
In this episode of GTMnow, Sophie Buonassisi sits down with Linda Tong, CEO of Webflow, to unpack how the entire web is being rewritten for a world where humans AND AI agents are your audience.
Linda breaks down why Webflow is no longer "just a website builder" (it's an agentic web marketing platform), what the Vidoso acquisition unlocks for AI-generated brand assets, and how the rise of Answer Engine Optimization (AEO) is forcing marketers to rethink content from the ground up. She also shares the practical playbooks her team uses to "vibe" sites into production with the Webflow MCP server, why human creativity is the only real moat left, and how she built her own personal CRM using Claude Code.
If you run a GTM team, lead marketing, or are trying to figure out what your website should even look like in 2026, this one is essential.
WHAT YOU'LL LEARN -Why your website is now the #1 source of truth for humans, bots, and agents -The shift from static sites to continuously optimizing, dynamic experiences -How "vibe coding" with MCP is changing the way teams build on the web -Inside the Vidoso acquisition and what "brand-governed AI" actually means -AppGen: going from prompt to production without losing brand consistency -Answer Engine Optimization (AEO): the non-obvious mistakes marketers are making -How to structure a marketing team made of humans plus agent swarms -The "5 words" exercise every CEO should run inside their company -Linda's personal CRM built with Claude Code (and how Webflow scales internal AI) -Why "unlimited credits" and Builder Days unlock real AI productivity
ABOUT THE GUEST Linda Tong is the CEO of Webflow, the agentic web marketing platform powering some of the most respected brands on the internet. Before stepping into the CEO role, Linda served as President and COO at Webflow, and previously led product at Cisco's AppDynamics and held senior roles at Google.
CHAPTERS 00:00 Intro 01:41 From static to dynamic 03:12 Inside the Vidoso acquisition 05:38 The human moat 07:17 Beyond the website builder 08:55 Structuring human + agent teams 09:58 AppGen, explained 10:45 Prompt to production 12:11 AEO misconceptions 14:40 Holistic AEO strategy 16:38 The 5 words exercise 18:10 Linda's personal CRM 19:31 Central vs. individual AI 20:44 Inside Webflow's Builder Days
Guest: Linda Tong, CEO Webflow https://www.linkedin.com/in/lktong/ https://x.com/YayLT
Host: Sophie Buonassisi, SVP at GTMnow https://www.linkedin.com/in/sophiebuonassisi/ https://x.com/sophiebuona
ABOUT GTMnow GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
Sponsors: .Tech - Domains, where the next generation of builders is planting their flag. Secure your .tech domain today from any registrar of your choice.
Transcript available under the episode here: https://gtmnow.com/tag/podcast/
Subscribe to GTMnow for the latest episodes! https://gtmnow.com
For inquiries about sponsoring the podcast, email gtmnow@gtmfund.com
GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Inside Reevo's $80M Bet to Kill the $10B Frankenstein Stack | David Zhu, Cofounder & CEO
14 mai 2026
00:41:58
AI is rewriting go-to-market and most companies are still operating with a “Frankenstein stack.”
In this episode of GTMnow, we sit down with David, founder & CEO of Reevo, to unpack how AI-native companies will replace legacy GTM systems, why the future of sales teams looks radically different, and how AI agents are becoming the new operating layer for revenue teams.
David shares why Reevo stayed in stealth while building a vertically integrated AI revenue operating system, the problem of institutional knowledge loss in sales organizations, and why the old playbook for SaaS and GTM is breaking in 2026.
We also dive deep into: - AI-native go-to-market strategy - The death of the legacy SaaS tech stack - Revenue operating systems explained - AI agents for sales, marketing, and customer success - How founders should think about AI adoption - Building startups in the age of AI - Why “failure is the cornerstone of innovation” - AI-driven sales productivity and revenue efficiency - Founder-led sales in 2026 - The future of CROs, CMOs, and RevOps - AI copilots, Jarvis-style workflows, and GTM automation - Scaling teams without scaling headcount
If you're a founder, CRO, CMO, GTM leader, SaaS operator, AI builder, or investor trying to understand where B2B software and go-to-market are headed next, this episode is for you.
Timestamps: 00:00 Intro 01:20 Why Reevo built in stealth 04:50 Why AI can finally disrupt GTM tech stacks 09:20 What Reevo actually does 11:10 AI outcomes vs headcount growth 15:00 How AI changes leadership & innovation 19:00 Why legacy GTM teams are vulnerable 23:00 The future of AI-native GTM organizations 29:00 Running an AI-native company internally 34:00 David’s favorite AI workflows & tools 37:40 Advice for introverted founders & leaders
Host: Sophie Buonassisi, SVP Marketing at GTMnow https://www.linkedin.com/in/sophiebuonassisi
Guest: David Zhu, Co-founder and CEO at Reevo https://www.linkedin.com/in/zhuventures/
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
Sponsors: .Tech - Domains, where the next generation of builders is planting their flag. Secure your .tech domain today from any registrar of your choice.
Transcript available under the episode here: https://gtmnow.com/tag/podcast/
Subscribe to GTMnow for the latest episodes! https://gtmnow.com
For inquiries about sponsoring the podcast, email gtmnow@gtmfund.com
GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
VC: "Software Is Basically Worth Zero Now" | Tyler Hogge, Ex-Pelion
12 mai 2026
00:47:40
Tyler Hogge helped take Divvy from zero to a $2.5B acquisition by Bill.com. Now, as General Partner at Pelion Ventures, he argues that charging for software is dead, per-seat pricing is collapsing, and the next decade of venture-scale companies will be built on outcomes, not subscriptions.
In this episode of the GTMnow VC Podcast, Tyler sits down with Max to break down what comes after SaaS pricing, why founder intensity is the only trait that still matters in 2026, and how Pelion concentrates capital into its biggest winners (Cloudflare alone returned over $1B to the fund). He also shares why most startups won't survive going head-to-head with OpenAI and Anthropic, the "bent the odds" contract he signed with Redo's CEO, and the lesson from raising four kids that changed how he leads.
This is an honest, no-fluff conversation about where venture is going as AI commoditizes software.
Chapters: 00:00 Intro 01:14 Intro 18:48 Tyler joins 23:09 "Sell Jesus, sell anything" 27:42 The $2.5B Divvy exit 34:39 The "bent the odds" contract 38:11 Startups vs. OpenAI and Anthropic 39:05 "Software is worth zero" 40:55 The death of per-seat pricing 43:02 Lessons from raising 4 kids 46:44 "LinkedIn is the trailer park"
Connect with Tyler: https://x.com/thogge https://www.linkedin.com/in/thogge/
Connect with Max: https://x.com/hackitmax https://www.linkedin.com/in/maxaltschuler/
Connect with Paul: https://x.com/PaulGTM https://www.linkedin.com/in/paulsirving/
About Tyler Hogge: Tyler Hogge is a General Partner at Pelion Ventures, Utah's oldest and largest venture fund with $500M AUM across eight funds. Before Pelion, Tyler was VP of Product at Divvy, which sold to Bill.com for $2.5B in 2021. Earlier in his career, he was a product leader at Wealthfront under Andy Rachleff and Adam Nash. He's based in Utah and one of the most active venture capitalists on X.
About GTMnow: GTMnow is the media arm of GTMfund, a pre-seed and seed-stage B2B SaaS venture firm backed by an LP base of 300+ C-suite and VP-level operators from the best go-to-market organizations in tech. The GTMnow VC Podcast publishes every other week with the investors and operators shaping the next decade of B2B software.
Brought to you by: AngelList From starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure allowed us to scale without sacrificing agility, from onboarding hundreds of LPs seamlessly to handling compliance, capital calls, and reporting as our fund size evolved.
Transcript available under the episode here: https://gtmnow.com/tag/podcast/
Subscribe to GTMnow for the latest episodes! https://gtmnow.com
For inquiries about sponsoring the podcast, email gtmnow@gtmfund.com
GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
How AI Will Go From Influencing 20% to Making 90% of Your Decisions | Steve Lucas, Boomi CEO
06 mai 2026
00:12:43
Boomi was founded in the early 2000s by Rick Nucci, acquired by Dell in 2010, and then spun out to Francisco Partners and TPG Capital in 2021. Today it powers 30,000+ enterprise customers globally and moves more data per second than the entire Visa card network, times two. What started as an integration platform has evolved into something bigger: the leading data activation company, purpose-built for the agentic AI era.
Steve Lucas took over as CEO in early 2023, just as ChatGPT was about to reshape the entire software landscape. A three-time CEO with nearly 30 years in enterprise software, Steve previously led Marketo through its $4.75B acquisition by Adobe (the largest in Adobe's history at the time), scaled iCIMS into the world's leading talent acquisition cloud, and held senior roles at SAP, Salesforce, Adobe, and BusinessObjects. He's also the author of "Digital Impact: The Human Element of AI Driven Transformation," a book arguing that the AI revolution will stall unless companies fix the fragmentation of their data first.
In this episode, Sophie Buonassisi sits down with Steve at HumanX in San Francisco to unpack why 2026 is the year AI moves from pilot to production, the three diagnostic questions every CEO should ask before deploying agentic AI, and why "change only happens at the speed of trust." Steve also gets candid about the internal protest that erupted when Boomi rolled out its first CSM agent, his prediction that AI will go from influencing 20% of executive decisions to making 90% of them within 2 years, and how he picked up Claude Code on an airplane to vibe-code a contracts agent for his sales team.
If you're a founder, operator, or GTM leader trying to figure out whether your business is actually ready for agentic AI (or just chasing the buzzword), this one is for you.
TIMESTAMPS
0:00 Intro
0:58 Welcome to GTMnow at HumanX
1:10 Why 2026 is when AI moves from pilot to production
2:32 Influencing decisions vs. making decisions: the next 2 years
3:18 Digital Impact: why fragmentation will stall the AI revolution
5:01 "Get your data to the gym": the new slogan
5:20 The 3 questions to know if your company is AI-ready
6:47 Change happens at the speed of trust
7:53 The internal protest behind Boomi's CSM agent
9:32 From integration platform to data activation: the strategic shift
10:50 Steve's most transformative AI workflow as a CEO
11:12 Vibe coding with Claude on an airplane
12:20 Where to follow Steve and Boomi
Host: Sophie Buonassisi, SVP Marketing at GTMnow
linkedin.com/in/sophiebuonassisi
Guest: Steve Lucas, CEO at Boomi
https://www.linkedin.com/in/nstevenlucas/
Visit us on: https://gtmnow.com
Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow
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Transcript available under the episode here: https://gtmnow.com/tag/podcast/
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For inquiries about sponsoring the podcast, email gtmnow@gtmfund.com
GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Okta's CRO: From $850M in Losses to $760M Profit (The AI Agent Bet) | Jon Addison
29 avr. 2026
00:40:18
Okta's CRO Jon Addison joins GTMnow host Sophie to break down the full story behind Okta's remarkable revenue turnaround, the launch of Okta for AI Agents, and the go-to-market playbook that's carrying them from $3B toward a $5B ARR target.
From nearly $850M in operating losses to over $760M in operating income, Okta's transformation is one of the most significant turnaround stories in enterprise SaaS. In this episode, Jon pulls back the curtain on exactly how it happened.
In this episode:
- Why 91% of enterprises are already deploying AI agents but only 10% have a security strategy for them
- How Okta's "AI governance gap" insight became the foundation for their biggest product launch in years: Okta for AI Agents
- The GTM restructure around specialization that unlocked productivity and drove 40% higher average contract value on new product deals
- How Okta became a partner-first company: 95% of their top 100 deals in the last fiscal year were partner-led, and what operationally made that possible
- Why the first discovery call no longer exists, and how sellers need to show up differently in the AI era
- Jon's new internal sales methodology, APEX, built on Command of the Message for the AI era
- How Okta is using AI internally to transform their own go-to-market motion, from conversational intelligence to pre-sales assistants
- What the path to $5B ARR actually looks like: enterprise expansion, international growth, public sector, and the massive new TAM unlocked by non-human identity
- Jon's leadership philosophy: why human-centric selling is becoming more critical as AI takes over the repetitive work
Host: Sophie Buonassisi, SVP Marketing at GTMnow
https://www.linkedin.com/in/sophiebuonassisi
Guest: Jon Addison, CRO at Okta
https://www.linkedin.com/in/jon-addison-3399175
Timestamp:
0:00 - Cold open
1:19 - Welcome + Jon's background: from London to Silicon Valley
1:52 - How Jon got into software and identity management
4:08 - Okta for AI Agents launch announcement
5:04 - 90% of customers live with agents, only 10% confident in securing them
6:31 - What's driving the governance gap in the market
7:53 - Speed of agent innovation must be matched by security and governance
8:36 - 40% higher ACV on deals that include new products
9:43 - Why consolidation around a single identity platform is resonating
11:45 - How AI agents unlock a massive new TAM for Okta
13:05 - Okta's turnaround: from $850M operating losses to $760M operating income
33:47 - The future of identity: SaaS disruption, consolidation cycles, and Okta's position
37:06 - Jon's leadership style: coaching reps and unlocking potential
39:01 - Positive vs. negative leadership and the 1-to-10 touchpoints framework
Visit us on: https://gtmnow.com
Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow
Follow us on X (Twitte
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
VC: Inside a16z's $1.7B Infrastructure Bet | Jennifer Li, General Partner
28 avr. 2026
00:38:18
Jennifer Li, Partner at Andreessen Horowitz (a16z), breaks down why the firm allocated $1.7 billion of its latest $15 billion fund specifically toward AI infrastructure, and what she's betting on next.
Jennifer has backed ElevenLabs from Series A all the way through Series D, watching it grow to an $11 billion valuation. In this episode, she explains what she saw in voice AI before anyone else did, what makes a founder worth backing regardless of the tech, and why the next wave of AI infrastructure is being rebuilt from the ground up.
In this episode:
- Why a16z bet $1.7B on AI infrastructure (and why now)
- The shift from cloud to AI-native infrastructure: storage, compute, orchestration, memory
- How ElevenLabs crossed the uncanny valley in synthetic voice
- Voice agents as the first AI category to truly scale in the enterprise
- What "king-making" in AI go-to-market actually looks like
- The traits that made Jennifer write a check for ElevenLabs on founder conviction alone
- Open source vs. frontier models: what 2027 looks like
- Why world models and vision language models are the next unlock
- AI and human creativity: why directors and authors won't be replaced
- How a 1-2 person studio can now make a full movie
Host: Sophie Buonassisi, SVP Marketing at GTMnow
https://www.linkedin.com/in/sophiebuonassisi
Guest: Jennifer Li, General Partner at Andreessen Horowitz
https://www.linkedin.com/in/jenniferhli/
https://x.com/JenniferHli
Connect with Max:
https://x.com/hackitmax
https://www.linkedin.com/in/maxaltschuler
Connect with Paul:
https://x.com/PaulGTM
https://www.linkedin.com/in/paulsirving
Timestamps:
0:00 - Cold open
1:06 - Max & Paul intro: are we in a bubble?
1:46 - AI vs. dot-com era: the key differences
4:55 - B2B SaaS disruption and value destruction (Thoma Bravo / Medallia)
6:39 - Intercom / Finn: crossing the chasm from legacy to AI-native
8:08 - Introducing Jennifer Lee, a16z General Partner
8:31 - Paul's key takeaway: the distribution era
9:41 - Why speed to default brand has never mattered more
11:33 - The ElevenLabs story: a16z led Series A, B, and C
12:02 - Why the seed strategy still works
13:37 - What the best founders do differently with model capabilities
15:58 - Jennifer Lee joins: why a16z raised $1.7B for infrastructure
16:22 - What existing infrastructure is being rebuilt for AI
19:19 - Specific areas a16z is focused on: models, storage, dev tools, security
20:35 - 90%+ of code now written by agents
21:52 - What Jennifer saw early in the 11 Labs / voice AI space
25:19 - Go-to-market in AI infrastructure: what's working
27:29 - Becoming the default brand: the "Kleenex effect" in AI
28:37 - What makes a founder worth backing on conviction alone
30:48 - Predictions for 2026/2027: open source catching up fast
31:39 - Most exciting new modalities: world models and vision language models
32:07 - AI and human creativity: can they coexist?
34:42 - What's blocking the creative AI future
36:05 - "The best ideas live in the graveyard"
36:57 - Closing advice: make AI tools your friends
Visit us on: https://gtmnow.com
Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow
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Brought to you by: AngelList
From starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
How Figma Scaled From $2M to IPO | Kyle Parrish (First Sales Hire)
22 avr. 2026
00:47:08
Kyle Parrish joined Figma as the first-ever sales hire when the company was doing $2M in ARR and helped scale it to $950M ARR. Figma then went on to IPO (FIG). But the path there was anything but smooth.
In this episode, Kyle breaks down what it actually took to build Figma's enterprise sales motion from scratch, including the no-discount rule that made procurement teams furious, the 40-hour interview weeks when hiring felt impossible to keep up with, and what it was like to lead a 300-person team through a failed $20B Adobe acquisition, and then have their best year immediately after.
We cover: - Why Figma refused to discount, even when Microsoft pushed back - How to hire the right first sales rep as a founder - The PLG to enterprise transition most companies get wrong - What the Adobe deal collapse actually felt like from the inside - How Figma went from 3 products to 8 overnight and launched into an IPO - What great sales look like in the AI era
Timestamp: 0:00 – Intro 1:02 – Guest intro: Kyle Parrish 1:35 – Joining Figma at $2M ARR in 2018 5:01 – First meeting with Dylan (Figma CEO) 6:13 – How to find your first sales hire 9:05 – Stage alignment in early hiring 11:43 – Early-stage operators need "scar tissue" 13:19 – Northstar metric at Figma 14:13 – Obsessing over customer conversations 16:44 – Building Figma's brand through community 17:31 – Scaling the "unscalable" 20:08 – In-person GTM vs. digital 22:47 – Was there a moment Figma might not make it? 24:48 – Pivoting after the Adobe deal collapsed 28:10 – Figma's no-discount rule 31:05 – Enterprise ELAs replacing discounting 34:47 – What makes a great salesperson in the AI era 36:56 – Missionaries vs. mercenaries in AI-era GTM 39:47 – Spotting the next Dropbox or Figma 43:46 – Kyle's post-Figma investing focus 45:58 – Family, travel & what's next
Guest: Kyle Parrish, former VP Sales at Figma LinkedIn: https://www.linkedin.com/in/kparrish8/ X: https://x.com/KyleHParrish
Host: Sophie Buonassisi, SVP Marketing at GTMnow LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ X: https://x.com/sophiebuona
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
Sponsors: Nooks - the AI workspace for outbound teams: https://www.nooks.ai/gtmfund .Tech - Domains, where the next generation of builders is planting their flag. Secure your .tech domain today from any registrar of your choice.
Transcript available under the episode here: https://gtmnow.com/tag/podcast/
Subscribe to GTMnow for the latest episodes! https://gtmnow.com
For inquiries about sponsoring the podcast, email gtmnow@gtmfund.com
GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
How AI Killed the Discovery Call | Sam Senior, Founder & CEO of TestBox
16 avr. 2026
00:57:06
AI isn't just changing how we sell. It's changing how buyers make decisions before they ever talk to you.
Sam, Founder and CEO of TestBox, joins Sophie on GTMnow to break down exactly what's happening to the B2B software buying process right now, and what go-to-market leaders need to do about it immediately.
If you're a founder, CRO, or AE wondering why your pipeline feels different, this conversation will give you a clear framework for what's happening and what to do next.
What we cover:
Why 70-80% of purchase decisions are already made before the first call (and it's accelerating)
The shift from discovery calls to validation calls, and how to prepare
CEO (AI-version of SEO): how LLMs are shaping what buyers believe about your product
The "day one shortlist" shrinking from 3-4 vendors to 1-2 vendors
Agent-to-agent procurement: Sam's timeline for when AI agents fully take over buying
Why the mid-funnel is actually getting longer, not shorter
The "Fake Nothing, Prove Everything" campaign that went viral post-Series A
How TestBox runs 15 AI experiments per week across the entire company
Using Google Vertex video analysis to read prospect body language on sales calls
How to build an AI-first culture without burning out your team
Books: The 15 Commitments of Conscious Leadership, No Ego, Courageous Marketing, Good to Great
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
VC: Your First VC Meeting Will Be Agent-to-Agent | Auren Hoffman (Flex Capital)
15 avr. 2026
00:57:15
Auren Hoffman (Flex Capital) joins the GTMnow podcast to share some of the most contrarian takes in tech today, from why AI moats are gone, to why your next VC meeting will be with a bot, to why AI is secretly going to trigger a baby boom.
In this episode: - Why Auren runs 500+ AI agents to source deals, and what that means for founders raising capital - The "agent-to-agent" meeting prediction: by end of 2026, first VC conversations will be fully automated - Why every software moat has been "blown up" and what Salesforce, LinkedIn & DocuSign need to do to survive - The OpenAI x The Hustle acquisition breakdown: why it's the smartest (and cheapest) distribution play in AI - Why missing a great deal is 10x more painful than making a bad one, Auren's honest VC mistake framework - The baby boom thesis: why AI, IVF, self-driving cars & cheaper energy could reverse the fertility decline - Why companies won't sign yearly SaaS contracts anymore, and what that means for every B2B founder
Auren Hoffman is the founder of Flex Capital, SafeGraph, and LiveRamp. He's an early backer of Replit, Perplexity, Rippling, Vercel, Coinbase, Chime, and AppLovin.
Connect with Max: https://x.com/hackitmax https://www.linkedin.com/in/maxaltschuler
Connect with Auren: https://x.com/auren https://www.linkedin.com/in/auren/ https://www.youtube.com/@summationpod
GTMnow shares how the best in tech build, scale and invest.
Visit gtmnow.com for more episodes, The GTMnow Newsletter editions, and other content.
GTMnow is run by GTMfund - we are an early-stage venture firm made up of 350+ go-to-market executives from the fastest-growing companies.
Chapters: 00:00 - Intro 01:05 - GTMfund Q1 recap 02:38 - OpenAI x The Hustle breakdown 06:18 - Redpoint's optimal VC deployment period 11:24 - Auren Hoffman intro 13:04 - Why am I seeing this deal? 26:26 - Sizing up founders at Replit, Perplexity & Rippling 28:49 - What separates great founders 32:10 - 500+ AI agents for deal sourcing 33:40 - Agent-to-agent VC meetings by 2026 45:13 - Every software moat is blown up 49:09 - Who kills Salesforce next? 51:30 - Why no one signs yearly SaaS contracts anymore 51:50 - AI will trigger a baby boom 56:22 - Thinking generationally
Visit us on: https://gtmnow.com Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow Follow us on X (Twitter): https://x.com/GTMnow_ Follow us on YouTube: https://www.youtube.com/@GTM_now Follow us on TikTok: https://www.tiktok.com/@gtmnow_ Follow us on Instagram: https://www.instagram.com/gtmnow_/
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
How One Hackathon Took Zapier’s AI Usage From 10% to 97% | CEO of Zapier
08 avr. 2026
00:39:13
Wade Foster is the CEO of Zapier, a company that sits between 7,000+ apps and runs millions of automations every single day. That gives him a front-row seat to how companies are actually adopting AI, not just talking about it.
In this episode, Wade breaks down the exact decisions he made at Zapier to go from 10% AI usage to 97% company-wide, why agents and workflows are not the same thing, and what most leaders are getting completely wrong about AI fluency.
What you'll learn:
The difference between agents and workflows (and when to use which)
What triggered Zapier's internal "Code Red" after GPT-4 launched
The one-week hackathon that took AI adoption from 10% to 50% overnight
The AI fluency rubric Zapier built: Unacceptable, Acceptable, Adaptive, Transformative
Why leaders who aren't using AI are the biggest bottleneck in their companies
How to measure AI ROI: floor raisers vs ceiling raisers
How AI now handles 50% of Zapier's customer support tickets
Wade's personal "advisory council" of AI sub-agents he uses for every major decision
Why building a company today is 10x cheaper but distribution is 10x harder
The truth about fundraising: you're selling your company, not raising money
How Zapier stayed profitable by only hiring when it hurt
3:16 - Workflows vs. Agents: What's the difference?
6:09 - Zapier's Code Red moment
8:55 - The hackathon that moved AI adoption from 10% to 50%
12:06 - Making AI fluency a hiring requirement
13:47 - Building the AI fluency rubric
16:40 - Why leaders are the biggest AI bottleneck
18:12 - Revenue impact of going AI-first
22:09 - Would Wade build Zapier differently today?
23:20 - Is Zapier's moat at risk from agents?
24:59 - Staying profitable with minimal capital
28:37 - The riskiest contrarian bet that paid off
31:52 - Wade's 3 personal AI workflows
36:53 - Favorite books for founders
GTMnow is the media brand of GTMfund, sharing go-to-market insights from working with hundreds of portfolio companies backed by 350+ of the best GTM executives.
Subscribe for weekly episodes with the operators, founders, and investors behind the fastest-growing software companies.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
VC: Investing at Inception in the Age of AI Agents | Ed Sim (Founder & GP, Boldstart)
01 avr. 2026
00:49:46
Ed Sim has been a VC for 30 years. He's backed companies like Clay, Front, BigID, and Snyk. He writes What's Hot in Enterprise IT every single Saturday, 489 weeks in a row. And right now, he says this is the most exciting and terrifying moment he's ever seen in his career.
In this episode, Max and Ed break down what's actually happening inside startups and boards right now, why the old playbooks are dead, and what separates the companies that will survive this AI shift from the ones quietly getting killed by it.
Discussed in this episode
Why engineering is no longer your bottleneck (and what is)
The 5 P's Ed uses to evaluate every inception-stage investment
The autonomous enterprise thesis and what it means for how companies are built
Why AI-native leadership is now a survival reqxtuirement, not a nice to have
The full Clay story: $600K to $100M ARR, how they stayed lean, and what actually unlocked growth
The 3 CH's framework for being a great board partner to founders
Why the best founders today are inside the AI jet stream, not chasing it
What every board meeting sounds like right now
Episode highlights0:00 Intro &
1:05 Episode Preview: Ed Sim & Key Takeaways
3:10 The Jet Stream Analogy: Two Types of Companies
5:43 How GTM Operators Should Evaluate Companies Like Angel Investors
7:20 The Collapsing of Moats & AI-Native Business Opportunities
10:00 Rebuilding Industries vs. Selling Software to Them
15:00 Why Old GTM Playbooks Are Dead
17:46 Ed Sim's Background: From Cutco to 30 Years in VC
21:43 The Five P's of Inception Investing
23:04 How to Evaluate Potential & TAM in a Fast-Changing Market
25:40 Staying Ahead of the Jet Stream as a Founder
26:32 The Autonomous Enterprise Thesis
28:44 Agent of the Week: How Companies Should Adopt AI Agents
29:10 How Agents Are Changing Engineering Bottlenecks
31:15 What Incumbents Must Do to Survive the AI Wave
32:53 Intercom, Snowflake & How Legacy Companies Are Adapting
36:43 The Clay Story: How They Found Their Footing
38:33 The Three C's of Working With Founders (Cheer, Challenge, Chill)
40:07 Clay's Growth Trajectory: $600K to $100M+ ARR
41:10 Clay's Agency GTM Model & Community Moat
43:50 Ed's Fund Model: $500K to $15M Checks at Inception
46:57 What's Hot in Enterprise IT & Venture Right Now
48:03 Closing Remarks
Key takeaways1. Engineering is no longer your bottleneck. Your people are. Code is shipping faster than your sales, marketing, and customers can absorb it. The constraint has flipped completely and most companies haven't noticed yet.
2. Painkillers beat vitamins every time. The only startups worth backing at inception are solving a hair-on-fire problem someone desperately needs fixed, not a nice-to-have they can live without.
3. The 3 CH's of being a great board partner. Know when to Cheer (when founders are getting beaten up), when to Challenge (when they feel invincible), and when to Chill (when they just need breathing room to figure it out). Elliot used all three with Clay to perfection.
4. If your CEO came from sales, you are in trouble. Surviving this AI shift requires product-driven, agent-native leadership at the top. The companies that adapted, Snowflake, Intercom, Atlassian, all changed leadership first.
5. The best founders are inside the AI jet stream, not chasing it. The question Ed asks every founder today: are you struggling to keep up, or are you the one constantly shipping and adapting faster than anyone can copy you?
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The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
How Sophos Scales Customer Success for 600,000 Customers in a 24/7 Cyber Threat Environment, with Teresa Anania, SVP of Customer Experience
24 mars 2026
00:41:57
This episode was recorded prior to Teresa Anania’s move to Chief Customer Officer at Verint. At the time of recording, she was SVP of Customer Experience at Sophos.
Teresa Anania (CCO at Verint, formerly CCO at Sophos) joins GTMnow to share how she's built customer success into a true revenue engine at a company serving 600,000 customers across over $1 billion in annual revenue, and why the old reactive, relationship-based CS model is no longer cutting it.
At Sophos, the threat landscape is compounding fast. AI is accelerating the speed and sophistication of attacks, which means response times, customer journeys, and success motions all have to evolve in lockstep in order to keep up. Teresa has spent her career at companies like Zendesk, Autodesk, and ON24 building the operational frameworks that make that possible at scale.Mentioned Resources: Cleverbridge: Merchant of Record for Software & SaaSGuest links:
- HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at https://www.hockeystack.com/
- Nooks - the AI workspace for outbound teams, where AI agents handle prospecting, research, and sequencing so reps can focus on conversations. Learn more at https://www.nooks.ai/
- Cleverbridge – the digital commerce platform helping enterprises optimize post-sale revenue through renewals, winbacks, and add-ons with buyer-friendly purchasing experiences. Learn more at https://grow.cleverbridge.com/lp/digital-commerce
Transcript available under the episode here:
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Bonus Episode: GTMfund Hires a New Partner!
23 mars 2026
00:22:29
Jason Demant just joined GTMfund as Partner, Head of Networks after 6 years at Foundation Capital where he reviewed over 1,000 emerging manager funds and invested in 100+.In this episode, Max (GP), Paul (GP), and Jason break down what separates the VC firms that survive from the ones that quietly die, why the best founders today are skipping mega funds at pre-seed, and what LPs are excited in about emerging managers.What we cover:
The real reason raising from mega funds at pre-seed can backfire
Why less than 10% of VC firms ever make it to Fund 3
What makes an emerging manager fundable (sourcing, founder support, durability)
The media flywheel that gives certain funds an unfair advantage
How LPs should think about mega funds vs. emerging platforms (the barbell approach)
Why founders are the ones now choosing their investors, not the other way around
GTMnow is the media extension of GTMfund, a venture capital firm investing in early-stage B2B companies. Every episode features operators, investors, and founders on the front lines of go-to-market.
10:41 Building a VC Firm Is Like Building a Startup
12:31 Emerging Managers vs. Mega Funds (a16z, Lightspeed)
14:01 Why Top Founders Are Picking Emerging Managers for Early Rounds
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
Inside ServiceNow’s $10B Go-to-Market Engine with Paul Fipps
17 mars 2026
00:40:59
NEW: @Paul Fipps (President of Global Customer Operations at @ServiceNow) joins GTMnow to break down how ServiceNow built the customer engine behind $10B+ in revenue and 20%+ growth for five consecutive years.
From CIO at Under Armour overseeing a 300 million-member connected fitness ecosystem, to now leading global sales, customer success, field marketing, and partners at one of the most disciplined GTM organizations in enterprise software, Paul has seen what it takes to scale from both sides of the table.
In this conversation, you'll learn:
- Why complacency is a bigger threat than competition at scale
- How to detect churn long before it shows up in a report
- What a CIO cancelling 900 AI pilots tells you about where enterprise AI is actually headed
- How ServiceNow unified sales, customer success, field marketing, and partners into one GTM motion so customers never feel the org chart
- Why ServiceNow monitors customer health daily — and what signals their teams actually track
- How community became a core GTM advantage, not just a marketing channel
- How ServiceNow’s AI Control Tower governs agents across the enterprise stack
- Inside “Now on Now”: how ServiceNow generated $335M in annualized AI productivity gains using its own platform
- How integrating Claude into the GTM workflow cut account planning from days to minutes
- What DTC product thinking from Under Armour unlocked in enterprise GTM
- How ServiceNow shifted from 6-month product releases to monthly innovation cycles
- Paul’s advice for building a world-class GTM organization: put the best people in the right seats
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
What Wins When Anyone Can Build Anything with Brett Queener, Partner at Bonfire Ventures
17 mars 2026
00:59:43
Brett Queener (Partner at Bonfire Ventures) joins GTMnow to share what three decades across Siebel, early Salesforce, co-founding, and seed-stage investing has taught him about what actually wins now that software is cheaper and faster than he ever imagined.
Brett was one of the earliest GTM hires at Salesforce when it had seven employees. He helped build the go-to-market playbook that defined a generation of SaaS: enterprise segmentation, sales motion design, product marketing, the whole works. He then co-founded SmartRecruiters, angel invested in companies like Outreach and Pando, and eventually joined Bonfire Ventures as a Partner to do early-stage investing the way he thinks it should be done: hands-on, operator-led, and built around founders who are ruthless about execution.
From starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure allowed us to scale without sacrificing agility — from onboarding hundreds of LPs seamlessly to handling compliance, capital calls, and reporting as our fund size evolved.
As we expanded from Fund I to Fund II, AngelList took care of the back-office operations, allowing us to stay focused on what matters most: investing in world-class founders and building the strongest go-to-market network in venture.
They’ve scaled with us across funds and into the future.
00:00 – Brett's career: Siebel, Salesforce employee #7, co-founder, angel investor, seed-stage VC06:58 – The big shift: from passive CRUD apps to agentic software that does the work for you08:07 – "Failing upwards" and what the fastest-growing companies taught Brett about investing in people10:58 – Why Brett moved into VC: 25 years of operators whose collective worth hit $25B16:50 – What Brett looks for in founders now and how it's changed over 6-7 years18:05 – Why anybody can build anything: Brett builds a fully functional travel app in 15 minutes19:20 – The last remaining
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
AI at the Edge: How Armada is Taking Compute Everywhere the Cloud Can't Go | Dan Wright (CEO of Armada)
10 mars 2026
00:27:54
Dan Wright (Co-founder & CEO of Armada) joins GTMnow to unpack what it actually takes to bring AI infrastructure to the places the cloud was never built to reach.
The cloud covers about 30% of the world. The other 70% (think: oil rigs, the Arctic tundra, military ships, remote mines) is where some of the most critical decisions happen, making latency a life-or-death and billions of dollars difference. Armada is building the infrastructure for that part of the world: modular, ruggedized AI data centers that go to the data, instead of the other way around.
From the first offshore edge computing deployment with the US Navy, to cutting avalanche response times in Alaska from over a day to real time, to sovereign AI installations in Saudi Arabia with Aramco and Microsoft, Armada is redefining what operating at the edge even means.
In this episode, we cover:
- Why cloud infrastructure was built for a pre-AI world and what that gap costs
- How Starlink turned every remote location into a potential AI cluster
- What "distributed intelligence" means and why it's the founding principle behind Armada
- The global race for AI sovereignty and why modular compute is the linchpin
- How Armada goes to market when a product demo involves shipping a 40-foot container to a desert (yes, really)
- Why customer champions are better than any sales rep
- The Microsoft partnership and how Armada extends Azure to places Azure could never go on its own
- Category creation lessons from building a company before the market had a name for the industry
- What's next: SpaceX, sovereign AI, and why Dan thinks humans are on the moon in two years (yes, REALLY)
HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at https://www.hockeystack.com/
Nooks - the AI workspace for outbound teams, where AI agents handle prospecting, r
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM: Lessons from Figma, Dropbox, and Building Iconic Brands in the Age of AI with Figma’s CMO, Sheila Vashee
03 mars 2026
00:30:43
NEW: @Sheila Vashee (CMO of @Figma) joins GTMnow to share how she thinks about brand building across every stage. From selling brownies at age eight, to second marketing hire at Dropbox scaling to $1B+ in annualized revenue, to now leading marketing at one of the most beloved software brands in the world, Sheila has seen it all.
In this conversation, you’ll learn what brand actually means (hint: it's not your logo), how PLG companies make the leap to enterprise, why being obsessively close to your customers is a compounding advantage, and how AI is reshaping the marketing playbook without replacing the human craft that sets great brands apart.
- HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at https://www.hockeystack.com/
- Granola - the AI notepad that turns meetings into action by capturing context, decisions, and next steps automatically. Head to https://www.granola.ai/gtmfund and get three months free with the code GTMFUND.
00:00 – The brownie stand: why brand building started at age eight
03:55 – How Sheila defines brand: it's what people say when you're not in the room
05:08 – Joining Dropbox as the second marketing hire
06:07 – Space Race: the campaign that defined Dropbox's early strategy
06:56 – What consumer marketing taught her about driving revenue
08:29 – Measuring brand ROI through match market testing
09:15 – How Figma thinks about brand building at a macro level
11:21 – The PLG-to-enterprise equation: what Figma did early that Dropbox waited too long on
15:02 – Why building the enterprise team is both operational and optical
17:12 – How Figm
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
VC: 116 Quarters on Quota and What Every Sales Leader Should Be Tracking, with Bill Binch, Operating Partner at Battery Ventures
03 mars 2026
00:52:24
Bill Binch (Operating Partner at Battery Ventures) joins GTMnow to share the operational frameworks he's built across 116 quarters on quota, and what actually changes when you move from driving revenue to advising an entire portfolio.
Before Battery, Bill was employee #16 at Marketo, where he led sales from zero revenue through IPO and a Vista Equity acquisition. He then served as CRO at Pendo, helping scale ARR to nearly $100M in only three years. His career spans some of the most defining sales organizations in enterprise software, from Oracle to PeopleSoft.
From starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure allowed us to scale without sacrificing agility — from onboarding hundreds of LPs seamlessly to handling compliance, capital calls, and reporting as our fund size evolved.
As we expanded from Fund I to Fund II, AngelList took care of the back-office operations, allowing us to stay focused on what matters most: investing in world-class founders and building the strongest go-to-market network in venture.
They’ve scaled with us across funds and into the future.
00:00 – Bill's career path: Oracle, Marketo employee #16, Pendo CRO, and choosing Arizona over tech hubs
15:01 – Battery's approach: why there's no one-size-fits-all playbook
19:56 – Outreach's accidental sales experiment: remote vs. in-person results
21:23 – What nobody tells you about the transition from CRO to operating partner
23:01 – Gold watch and slippers? Why ope
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM: BREAKING: Inside Nooks’ Launch: Why AI-Native Sales Tools Are Challenging Legacy Platforms, with Co-Founder & CEO Dan Lee
24 févr. 2026
00:32:03
Dan Lee (Co-Founder & CEO of Nooks) joins GTMnow to give a behind the scenes on how Nooks is launching a new Agent Workspace and AI Sequencing layer designed to operate across the full action set of a rep’s day — calls, emails, research, prospecting, and strategy.
The conversation explores why top of funnel is changing the fastest, why traditional sequencing tools optimize the “move” but not the strategy, and how AI systems that learn from rep behavior can compound advantage over time. As adoption deepens, automation can move from ~40% of outbound execution toward 70% and beyond, while switching away resets that intelligence.
We also discuss the broader category shift: customers pushing AI-native tools to take on incumbents, the rise of agent workspaces as the new interface for GTM teams, and why calls remain the most data-rich channel in outbound compared to silent email non-responses.
Sponsors:
Granola - the AI notepad that turns meetings into action by capturing context, decisions, and next steps automatically. Head to https://www.granola.ai/gtmfund and get three months free with the code GTMFUND.
HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at https://www.hockeystack.com/
00:00 – Announcing the Agent Workspace and AI sequencing product
01:25 – Why sales is fundamentally human (even in the AI era)
02:39 – The Agent Workspace as the human–AI interface
02:56 – Why legacy sequencing tools were built for a manual world
04:14 – The sales chess analogy: understand the board before making the move
05:02 – Reps spend too much time "making the move"
06:00 – Nooks as a simulati
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM: The End of GTM Sprawl: How HockeyStack is Rebuilding Go-to-Market Around AI, with Co-Founder Emir Atli
17 févr. 2026
00:34:56
Emir Atli (Co-founder and CRO of HockeyStack) joins GTMnow to share how go-to-market is shifting in the AI era — from fragmented tools and GTM sprawl to unified, AI-native platforms built on a single data foundation.
Originally known for attribution and market intelligence, HockeyStack is evolving into a central operating system for go-to-market, spanning marketing, sales, and post-sales through AI agents, blueprints, and an execution layer.
We also explore weekly GTM sprints, founder-led content as a pipeline driver (even with <100 followers), and the long-game mindset behind building a generational company from age 20 after YC.
In this episode, we cover:- Why you can’t layer AI onto legacy GTM — you must rebuild GTM around AI
- The “sprawl crisis” and why siloed tools break without a single data foundation
- HockeyStack’s evolution from attribution to a unified GTM operating system
- AI agents, blueprints, and the shift from reporting to execution
- Why consolidation is moving from tools to full buyer journey control
- The case for a winner-takes-all GTM platform
- How AI increases leverage across reps, managers, and pipeline reviews
- Weekly GTM sprints and faster iteration cycles in the AI era
- Founder-led content as a core growth engine and pipeline driver
- LinkedIn as a top channel for MQL-to-opportunity and deal acceleration
- The 10-year mindset, YC lessons, and building a generational company
Sponsor:
Granola - the AI notepad that turns meetings into action by capturing context, decisions, and next steps automatically. Head to https://www.granola.ai/?via=gtmfund&dub_id=ytmcNnCjtlqCbgH5 and get three months free with the code GTMFUND.
00:00 – The GTM sprawl crisis and why AI breaks in siloed systems
01:50 – From attribution to a GTM operating system
02:41 – Launching AI agents, blueprints, and the execution layer in 2026
03:57 – Building a single data foundation across the buyer journey
05:09 – Why GTM must be rebuilt around AI (not layered with tools)
06:23 – Doing "more with more" and increasing management leverage
07:30 – Tool consolidation vs controlling the buyer journey
08:48 – 2026–2028: the great GTM consolidation wave
09:01 – The case for a winner-takes-all GTM platform
10:10 – Moat: data foundation + application layer
11:
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
VC: How VCs Evaluate Technical Founders (TAM, Moats & Diligence), with Amanda Robson, Founder and GP of Modern Technical Fund
17 févr. 2026
00:56:17
Amanda “Robby” Robson (Founder of Modern Technical Fund) joins GTMnow to break down how she evaluates companies at the very earliest stages and why discipline matters more than ever in today’s market.
Amanda has spent over a decade in venture before launching Modern Technical Fund, investing across verticals ranging from security and compliance to developer tools at firms like Norwest and Cowboy Ventures. Her investment thesis is centered on backing elite technical founders early and helping them translate deep engineering talent into real products, real customers, and real momentum.
In this conversation, we unpack how Amanda thinks about founder quality, market timing, and risk when there’s limited data and plenty of noise, which is more critical than ever in an AI-heavy investing environment.
From starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure allowed us to scale without sacrificing agility — from onboarding hundreds of LPs seamlessly to handling compliance, capital calls, and reporting as our fund size evolved.
As we expanded from Fund I to Fund II, AngelList took care of the back-office operations, allowing us to stay focused on what matters most: investing in world-class founders and building the strongest go-to-market network in venture.
They’ve scaled with us across funds and into the future.
Subscribe to GTMnow for the latest episodes! https://gtmnow
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM: How Intercom Built the Highest-Performing AI Agent on the Market Using Outcome-Based Pricing with Archana Agrawal, President at Intercom
10 févr. 2026
00:46:29
Archana Agrawal (President of Intercom) joins GTMnow to share how Intercom (founded in 2011) successfully restructured its product, pricing, and go-to-market to become AI-native at a speed and scale most legacy SaaS companies haven’t achieved.
Their agent, Fin, now handles 80%+ of support volume, resolves 1M customer issues per week, and has grown from $1M to $100M+ ARR with a $0.99 outcome-based pricing model backed by up to a $1M performance guarantee if resolution targets aren’t met.
In this episode, we cover:
- Why customer support is fundamentally a 24/7 business
- How Fin now handles 80%+ of customer queries through automation
- Why human empathy often breaks down in real-world support workflows
- How AI makes instant, individualized service possible for the first time
- Why Intercom put a million-dollar guarantee behind its resolution rate
- What it takes to confidently price software on outcomes
03:23 – What Fin is and how it changes customer support
05:27 – How Fin scaled to a 6
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM: Why Most Founders Build the Wrong Company (And Realize It Too Late), with Lou Shipley, Former CEO and Co-Author of Unlikely Entrepreneurs
03 févr. 2026
00:45:42
Lou Shipley (three-time CEO, Harvard Business School professor, and author of Unlikely Entrepreneurs) joins GTMnow to break down why most founders struggle to turn good ideas into great companies.
Lou has led companies through acquisitions, teaches sales and go-to-market at Harvard, and has spent decades studying what actually separates companies that scale from those that stall.
In this conversation, we unpack why understanding customer pain and learning how to sell are still the two most important founder skills, especially as product moats decline and go-to-market becomes the real differentiator.
In this episode, we discuss:
- Why understanding customer pain matters more than having a great idea
- Why early selling should optimize for learning, not revenue
- Why founders can’t outsource sales too early
- How distribution becomes a competitive advantage at scale
- What makes “unlikely entrepreneurs” outperform expectations
- Why small, high-quality teams beat large organizations
- Why churn is a symptom, not the root problem
- How product-market fit quietly changes as companies grow
- Why founders must evolve from heroic sellers to system builders
- How culture becomes a real go-to-market asset
Lou also shares lessons from teaching sales at Harvard, profiling 13 unlikely entrepreneurs, and working with founders who realized too late that they were building the wrong company for the wrong customer.
If you’re a founder, operator, or investor trying to avoid costly early mistakes and build a company that actually scales, this episode will give you a clearer mental model for what matters most.
Timestamps:
00:00 – What actually makes a company great
00:26 – Why early selling is about learning, not revenue
01:47 – Why founders misunderstand customer pain
02:06 – “If you build it, they will come” is a lie
02:33 – Distribution as the real moat
02:58 – What makes an “unlikely entrepreneur” succeed
06:15 – Why age and experience increase founder success
07:01 – Curiosity, coachability, and risk elimination
09:29 – Why founders can’t outsource sales too early
15:26 – Pattern recognition vs short-term ARR
21:10 – Founder-led sales vs scalable systems
29:12 – Leadership, culture, and delegation
33:18 – Founder evolution from $1M to $100M
38:24 – When product-market fit starts to break
39:15 – Why churn is a lagging indicator
39:54 – Why small teams outperform large ones
44:22 – Lessons from Unlikely Entrepreneurs
45:23 – Final advice for founders
Sponsors:
HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at hockeystack.com
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM: Why AI Is Killing Your Outbound and Making In-Person GTM Inevitable, with Healey Cypher, CEO at BoomPop
28 janv. 2026
00:47:08
Healey Cypher (multi-time founder and CEO of BoomPop) joins GTMnow to unpack one of the fastest growing channels for company growth: in-person events.
As AI floods digital channels with perfectly personalized messages, trust is becoming harder to earn online. Healey explains why events, dinners, and in-person experiences are becoming a premium GTM channel, not a nice-to-have, and how founders can use them intentionally for distribution, alignment, and acquisition.
In this episode, we discuss:
- Why in-person events are becoming a premium GTM channel in an AI-first world
- How founders can de-risk distribution before building the product
- The most common internal missteps that derail startups early
- Why offsites are the new HQ for remote and hybrid teams
- How to design offsites that drive alignment, not just fun
- What makes a dinner actually work — including overlooked details like acoustics
- How teams use events for customer acquisition and partnerships
- Why kindness and positivity can be a real leadership advantage
Healey also shares a powerful insight from Sam Altman that reframes how we should think about AI’s impact on trust and human connection.
If you’re interested in scaling events as a growth channel, this episode will give you all the details you need and an understanding of what is working in today’s world.
Timestamps:
00:00 – Why founders underestimate distribution
03:30 – Product vs distribution: what actually matters early
06:45 – Why most startups fail from internal misalignment
10:30 – Culture, communication, and focus as scaling constraints
14:40 – Hybrid work broke alignment
17:45 – Why offsites are becoming the new HQ
21:30 – Events as a go-to-market strategy
25:00 – AI, outbound fatigue, and inbox trust collapse
28:40 – “In-person experiences are becoming a premium”
32:30 – How to use events for customer and partner acquisition
36:15 – What makes a high-impact event vs a wasted one
39:50 – Dinners, summits, and unforgettable experiences
43:30 – Leadership, kindness, and “don’t be a jerk”
47:40 – Mental state as a competitive advantage
52:30 – Final reflections and advice for founders
Sponsors:
HockeyStack - the AI platform that unifies GTM data to help teams convert, expand, and scale. Learn more at hockeystack.com
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM: Why Most Go-To-Market Motions Collapse at Scale, with Jeanne DeWitt Grosser, COO at Vercel
22 janv. 2026
00:45:07
Why do so many go-to-market motions fall apart right when a company starts to scale?
In this episode of GTMnow, Sophie Buonassisi sits down with Jeanne DeWitt Grosser, former GTM leader at Google and Stripe and now COO at Vercel, to unpack why GTM fragility is one of the most underdiagnosed risks in startups and scaling companies.
This is a deep, operator-level conversation about what actually breaks in sales, why AI won’t magically fix it, and how the best teams treat go-to-market like a product that must be designed, tested, and iterated.
If you are a founder, operator, or investor navigating growth, this episode will give you clearer mental models for building GTM that actually holds up under pressure.
In this episode, we cover:
Why most GTM motions fail at scale, even with strong products
What it really means to treat go-to-market like a product
How AI changes execution without changing fundamentals
The rise of the forward deployed engineer
Why “lost on price” is usually a lie
What great sales reps still do better than anyone in the AI era
How to think about joining companies “early” without getting timing wrong
Listen if GTM feels fragile, unpredictable, or overly dependent on heroes.
Timestamps
00:00 – Introduction
01:00 – “Yes is great. No is great. Maybe will kill you.”
02:00 – Why go-to-market should be treated like a product
04:45 – Designing the experience of being sold to
06:30 – Using AI to debug GTM process failures
09:00 – Why “lost on price” usually isn’t about price
12:00 – What go-to-market engineering actually is
16:00 – The rise of the forward deployed engineer
20:45 – AI, agents, and what still needs human judgment
25:45 – What great sales reps do differently in the AI era
29:30 – Why GTM roles are becoming more consultative
33:30 – Will there be an AI reckoning?
38:00 – What “joining early” really means
42:00 – Career lessons from Google, Stripe, and Vercel
44:00 – Closing thoughts
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
VC 3: Investing Philosophy for 2026: What Founders Should Know
20 janv. 2026
01:11:40
Mark Goldberg is a Managing Partner and Co-Founder at Chemistry, a new early-stage venture firm with a $350M debut fund backing standout software companies from Seed to Series A. Prior to Chemistry, Mark was a Partner at Index Ventures, where he led early-stage investments across software and fintech for nearly a decade. Before Index, Mark was one of the first business hires at Dropbox, helping the company navigate hypergrowth.
Discussed in this episode
Why Mark studied international relations, and why venture feels like “the liberal arts of jobs”
Index’s US “invisibility” era and what that taught him about building a new firm
The Chemistry spinout thesis: “take great multi-stage DNA, reconstitute it with focus”
Fund design: pre-seed → seed → A, light reserves, and concentrated doubling-down
Culture principles: excellence, performance, “no one takes themselves too seriously”
Conviction-based investing vs consensus IC, and why omissions are the real killer
The hardest lesson in venture: managing co-founder dynamics (and when to just listen)
Episode highlights
00:00 — “A+ people want to work with A+ people.”
01:46 — GTMfund’s 2026 prediction: big players come roaring back (Google, Meta, Microsoft, Uber/Waymo).
14:51 — GTMfund platform metrics: thousands of support items, intros, hires, and fundraising connects.
26:29 — Why Mark left Index to build Chemistry: big-fund lessons, rebuilt with focus.
33:39 — Chemistry’s strategy: early-stage focus, light reserves, and building for “product-market discovery.”
44:05 — “Venture doesn’t scale well.” Why Chemistry stays small to avoid bureaucracy.
49:59 — Events that actually work: chess tournaments, surfing, and hobby-driven gathering > happy hours.
54:56 — Investment process: conviction, not consensus—optimize for outliers, not averages.
1:10:32 — Hardest lesson in venture: co-founder dynamics, and learning when to listen (not “advise”).
Brought to you by: AngelList
From starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure allowed us to scale without sacrificing agility — from onboarding hundreds of LPs seamlessly to handling compliance, capital calls, and reporting as our fund size evolved.
As we expanded from Fund I to Fund II, AngelList took care of the back-office operations, allowing us to stay focused on what matters most: investing in world-class founders and building the strongest go-to-market network in venture.
They’ve scaled with us across funds and into the future.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.
GTM 174: The 7% Rule: How AI Is Rewriting Customer Success Budgets (From 10% to 7%) with Abbas Haider Ali
14 janv. 2026
00:52:41
Abbas Haider Ali is SVP of Customer Success at GitHub, where he leads a 550+ person post-sales organization supporting a $2B+ ARR business serving over 150 million developers, including more than 90% of the Fortune 100.
Previously, Abbas was VP of Customer & Partner Success at Twilio following its acquisition of Segment, and has held executive roles at xMatters, Opnet Technologies, Managed Objects, and IBM. He is also a General Partner at GTM Operators Network, investing from seed through growth, and is deeply committed to mentorship and advancing underrepresented leaders in tech.
Discussed in this episode:
Why “AI-led growth” can hide churn and value erosion
Lagging vs leading indicators for retention endurance
Why the CS investment benchmark is shifting from 10% → ~7%
A simple “waterfall” for allocating post-sales budget: support → onboarding → outcomes
How to “lever up” the envelope with premium support + professional services
Why expansion (not renewals) is the early signal of product-market fit
The rise of AI-powered specialized generalists in post-sales
When forward deployed engineers make sense (and when they’re just a fad)
Episode highlights
00:00 — Why customer expansion is the real signal of product-market fit
00:50 — Lagging revenue vs. leading indicators of endurance
04:11 — Why the CS benchmark dropped from 10% to 7%
08:41 — How AI moved from internal efficiency to customer-facing leverage
11:41 — Why retention cost matters more than CAC in the AI era
14:17 — The simplest framework for allocating the 7% CS budget
18:53 — Founder-led CS, design partners, and early-stage PMF myths
23:16 — The rise of AI-powered specialized generalists
30:00 — When forward-deployed engineers actually make sense
49:31 — The one rule for building a durable SaaS company
This episode is brought to you by our sponsor: HockeyStack
If you run go-to-market, you already know the problem: your data lives everywhere. Spreadsheets, CRMs, sales calls, ad platforms… yet you’re still guessing what to do next.
HockeyStack is the AI platform for modern GTM teams. It unifies all your sales and marketing data into a single system of action. Built-in AI agents help teams prospect the right accounts, improve conversions, close and expand deals, and scale what works. That’s why teams like RingCentral, Outreach, ActiveCampaign, and Fortune 100 companies rely on HockeyStack to eliminate wasted spend, take better decisions, and make space to think.
The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.