The GTMnow Podcast – Details, episodes & analysis

Cassie Young is a General Partner at Primary Venture Partners, a $1B AUM early-stage firm in New York backing category-defining SaaS, fintech, and vertical software companies. Before investing, she spent 15 years as a GTM operator, serving as Chief Revenue Officer at Sailthru and later Chief Customer & Commercial Officer at Marigold (Campaign Monitor, Sailthru, and other martech brands), where she scaled global sales, marketing, and customer success organizations.

Today, Cassie leads investments while also running Primary’s Impact program, giving founders access to a 30-person team across talent, GTM, and strategic finance, and she continues to teach operators through programs like Pavilion and Duke’s Innovation & Entrepreneurship board.

Discussed in this episode:

• How Cassie “accidentally” became a VC after 15 years in GTM leadership.
• The career advice Bill Gurley gave her that changed her trajectory.
• Why Primary refuses to say “platform” and instead built a 30-person Impact team.
• How she actually sources pre-seed/seed founders before they leave their jobs.
• Primary’s 5-part Founder Outcomes Framework (vision, talent, JDCE, and more).
• The difference between real traction vs. “happy ears” and fake design partners.
• Why she’s picky on GTM/AI tools and looks for step-change, not incremental gains.
• How operators can actually break into VC (hint: it’s all about doing the work).

Episode highlights

00:35 — Clay, usage-based pricing, and the $100M ARR rocketship

09:10 — The real story on AISDR: where AI reps actually work (and where they really don’t)

14:02 — Inside “The Gross Retention Apocalypse” and why AI experimental budgets are a ticking time bomb

22:46 — How Cassie accidentally became a VC and the Bill Gurley advice that changed her career path

27:17 — Why Primary hates the word “platform” and how Cassie built a 30-person Impact team for founders

36:10 — Cassie breaks down her 5-part founder outcomes framework (including “jaw-dropping customer experience”)

46:01 — Avoiding “happy ears”: how founders should really use design partners and MedPick-style rigor

57:48 — Time to value as the new north star and why nailing a tight wedge beats peanut-buttering features

1:01:29 — So you want to be a VC: Cassie’s playbook for operators to break into venture (without delusion)

Brought to you by: AngelList

How did we build the GTMfund back office? Easy!

We leveraged AngelList’s Rolling Fund product for Fund I, which was the perfect vehicle to scale up GTMfund in its first iteration. This structure allowed us to build our network, and add revenue leaders while we raised and deployed capital simultaneously, which was crucial for getting early points on the board and building relationships with founders.

For Fund II, we transitioned to a traditional closed-end fund structure through AngelList. This time with institutional investor support. This model allowed us to be more intentional about our portfolio construction. We worked closely with the AngelList team throughout this process, and they were incredible — always there to support us and our LPs every step of the way.

If you’re raising a fund or are looking to migrate your fund, we highly recommend you check them out. You can do so at www.angellist.com/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.

Dave Boyce is a go-to-market–focused technology executive, author of Freemium, and longtime SaaS operator and board member. Over two decades leading and advising B2B companies, he’s helped founders navigate the shift from sales-led to product-led, from gut-driven to instrumented, and now from manual GTM to AI-assisted systems. Today, Dave teaches revenue architecture and PLG through Winning by Design’s Growth Institute, works with leadership teams on Bow Tie–based growth models, and is all-in on how AI will reshape GTM as a true engineered system.

Discussed in this episode

• Why classic sales & marketing playbooks haven’t caught up to how modern buyers actually buy.
• How the Bowtie model exposes the real levers of growth that funnels hide.
• Why PLG-style thinking is now essential even for sales-led and enterprise motions.
• The 3 first principles of freemium: empathy, generosity, and metrics.
• Where AI can reliably outperform humans across the customer journey, and where it absolutely shouldn’t.
• How to design hybrid human + AI workflows using a clear data model, not vibes.
• What RevOps should own in a modern revenue architecture (and why it can’t just serve the CRO narrative).
• Hard-earned founder lessons from Fundly on reinvention, calling bets early, and letting go of old branches.

Episode highlights

00:00 — GTM is still running 20-year-old playbooks

01:29 — “Sales, marketing, CS… the last unengineered engine”

03:20 — The myth of “just add more heads”

05:50 — The Fundly story: reinvention, too late

08:30 — Why Freemium had to be written

11:01 — Three first principles of freemium

15:25 — Mapping AI across the entire customer journey

19:29 — “Automate the predictable, humanize the exceptional”

25:18 — What the Bowtie exposes that funnels hide

27:25 — Building a “minimum viable Bowtie

This episode is brought to you by our sponsor: ZoomInfo

ZoomInfo is the GTM Intelligence Platform built for sales, marketing, and RevOps.

By unifying data, workflows, and insights into a single system, ZoomInfo helps revenue teams find and engage the right buyers, launch go-to-market plays faster, and drive predictable growth. With industry-leading accuracy and depth of data, it gives your team the intelligence advantage to win in competitive markets.

It’s trusted by the fastest-growing companies and has become the category leader in GTM Intelligence.

Learn more at zoominfo.com.

Follow Dave Boyce (Guest)

• LinkedIn: https://www.linkedin.com/in/boycedave
• Substack: https://daveboyce.substack.com

Where to Find GTMnow

• Website: https://gtmnow.com
• LinkedIn: https://www.linkedin.com/company/gtmnow
• X (Twitter): https://x.com/GTMnow_
• YouTube: https://www.youtube.com/@GTM_now
• Podcast Directory: https://gtmnow.com/tag/podcast

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.

Guy Yalif is Chief Evangelist at Webflow and a veteran B2B marketing leader with 20+ years across Twitter, Yahoo, BrightRoll, and as co-founder/CEO of Intellimize (acquired by Webflow). He champions AI-driven optimization for sites and content, bringing a rare blend of aerospace-engineer rigor and operator experience from four successful exits to help teams win the shift from SEO to AEO.

Discussed in this episode

• Why AEO is an evolution of SEO (and what truly changes)
• The shift from keywords to “clusters of questions” as the new topic model
• Webflow’s four-part AEO framework: content, technical, authority, measurement
• Tactics that moved the needle: adding FAQs + schema; prioritizing freshness
• Why PR/brand and plain-text mentions matter more to AI engines
• How to measure AEO: presence in questions, share of voice, and sentiment
• Where to start: two moves any founder can ship this week
• Risks of ignoring AEO and the early-adopter advantage

Episode highlights

00:21 — “Your SEO resources are your AEO resources. This is an evolution, not a reset.”

01:15 — Webflow’s AEO promise: answer engines are a massive arbitrage—akin to early SEO/SEM/mobile.

03:00 — Why “ranking for keywords” is obsolete; topics = clusters of questions across the funnel.

07:49 — The 4-part AEO framework: content, technical (schema & structure), authority, measurement.

10:11 — Case study: Add ~6 FAQs + inline schema to product pages → half of new citations came from 6 pages; +24% organic in 2 weeks.

15:23 — If you only do two things: (1) answer questions comprehensively, (2) add schema metadata.

21:46 — Webflow data: AI-search traffic converts ~6x better than non-branded organic; unbranded share grew from 0% → 42% in a year.

24:02 — How buyers actually use LLMs in-flow; why your website still matters (to humans and machines).

29:58 — The learning curve is back: why AEO is resetting the playing field and rewarding curiosity.

This episode is brought to you by our sponsor:

ZoomInfo is the GTM Intelligence Platform built for sales, marketing, and RevOps.

By unifying data, workflows, and insights into a single system, ZoomInfo helps revenue teams find and engage the right buyers, launch go-to-market plays faster, and drive predictable growth.

With industry-leading accuracy and depth of data, it gives your team the intelligence advantage to win in competitive markets.

It’s trusted by the fastest-growing companies and has become the category leader in GTM Intelligence.

Learn more at zoominfo.com.

Follow Guy Yalif:

• LinkedIn: https://www.linkedin.com/in/gyalif/
• X (Twitter): https://x.com/gyalifX (formerly Twitter)
• Webflow author page: https://webflow.com/people/guy-yalif

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.

Leena Joshi is Co-Founder & CEO of CloseFactor, a GTM strategy and execution platform that helps enterprise tech hone in on the exact right prospective customers and accelerates their conversion by helping your sales and marketing teams be contextually relevant to them. 

She has led GTM teams at high scale B2B companies such as Splunk, VMware, Redis and has a unique perspective on the convergence of sales and marketing into an efficient, high performing GTM organization.

What You Will Learn:

• The differences in go-to-market motions across different stages of organizations. 
• The theme for the year is go-to-market convergence.
• Leena's experience finding the right go-to-market motion at CloseFactor. 
• Creating an outbound motion through inbound tracking. 
• How selling value is a tactic that is working for CloseFactor.

Highlights:
(14:08) Maintaining focus on the ICP in the early days, including turning revenue down.

(23:13) The importance of curiosity and a beginner's mindset.

(25:38) Finding a leader who has your back.

(28:19) Building a top-down sales strategy while maintaining a bottoms-up approach.

(32:28) The importance of hiring the right salespeople and balancing long-term and short-term thinking in sales.

(32:56) One thing revenue leaders believe to be true that Leena thinks is bull$***.

(36:03) One thing that is working for Leena in go-to-market right now.

Guest Speaker Link:
LinkedIn: www.linkedin.com/in/ljoshi/
Website: www.closefactor.com/

Host Speaker Links:
LinkedIn: www.linkedin.com/in/ssbarker/
Newsletter: thegtmnewsletter.substack.com/

Sponsor:
Common Room enables you to turn any buyer activity into pipeline. It ingests all of your product usage data, intent data, social activity, community conversations, and CRM insights to automatically surface high-intent leads and timely, relevant context so your sales reps can convert more customers and hit revenue targets faster. You can try it for free today, or book a demo to go deeper at www.commonroom.io.

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.

Mike Molinet is the Co-Founder of Branch (branch.io), where he was COO and President, leading the company to $100M in ARR. He oversaw all things GTM there, including G&A and Product. Now, he is the Co-Founder of Thena (thena.ai), a seed-stage startup backed by Lightspeed and First Round, where they're helping companies service and engage their customers in Slack. After taking Branch to $100M, he's doing it all over again, this time with a lot of learnings.

What You Will Learn:

• The different micro-phases within each stage of growth (0-1M ARR, 1-10M ARR, etc) and how leaders need to level up and adapt through each one.
• Hiring the right roles at the right time - AES vs leaders.
• Maintaining an open and learning mindset even with growing success.
• Relinquishing control as you scale while still providing oversight.
• Balancing product requests from large customers vs your overall roadmap.

Highlights:
(7:21) How your success comes from the people you hire and retain. 

(9:10) Evolving through micro phases through rapid growth. 

(15:50) Threading the needle on when to ask design partners for money in the early 0 to $1M stage. 

(23:11) Heuristic framework of evaluation for taking on bespoke build requests. 

(31:29) How hiring great people makes you feel excited to relinquish control.

(43:20) One thing revenue leaders believe to be true that Mike thinks is bull$***.

Guest Speaker Link:
LinkedIn: www.linkedin.com/in/mikemolinet/
Website: www.thena.ai

Host Speaker Links:
LinkedIn: www.linkedin.com/in/ssbarker/
Newsletter: thegtmnewsletter.substack.com/

Sponsor:
Common Room enables you to turn any buyer activity into pipeline. It ingests all of your product usage data, intent data, social activity, community conversations, and CRM insights to automatically surface high-intent leads and timely, relevant context so your sales reps can convert more customers and hit revenue targets faster. You can try it for free today, or book a demo to go deeper at www.commonroom.io.

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.

Eran Aloni is the Executive Vice President of Product Strategy and Ecosystem at Gong.  
He has been a leader at Gong for eight years, previously holding titles of Chief Customer Officer and Chief Operating Officer. 

What You Will Learn:

• Eran's career advice to younger go-to-market professionals. 
• Two stages of AI advancements and which is more valuable. 
• The role that data sets have in AI progressions. 
• How to continuously solicit team feedback to level up as a leader. 

Highlights:
(6:55) How AI solutions are still only scratching the surface in terms of driving deep, strategic value for customers.

(10:00) The competitive advantage players have with their access to rich, proprietary data sets to train AI. 

(18:12) Eran's biggest personal surprise from growing with Gong has been constantly challenging himself to develop new skills as the company scales.

(23:15) A story about early feedback Eran received as a young leader and how it shaped his future leadership.

(28:19) Why having core operating principles permeate through all levels of an organization builds trust.

(34:03) One thing revenue leaders believe to be true that Eran thinks is bull$***.

(37:22) One thing that is working for Eran in go-to-market right now. 

Guest Speaker Link:
LinkedIn: www.linkedin.com/in/eranaloni/

Host Speaker Links:
LinkedIn: www.linkedin.com/in/ssbarker/
Newsletter: thegtmnewsletter.substack.com/

Sponsor:
Common Room enables you to turn any buyer activity into pipeline. It ingests all of your product usage data, intent data, social activity, community conversations, and CRM insights to automatically surface high-intent leads and timely, relevant context so your sales reps can convert more customers and hit revenue targets faster. You can try it for free today, or book a demo to go deeper at www.commonroom.io.

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.

To cap off the year, we have another special episode. Be warned: It's a spicy one! 

At the end of every weekly podcast episode, host Scott Barker asks guests the same two questions. Last week, you heard the compilation of guest responses to the first question. This week, you’ll hear the compilation of their responses to the second question:

What is one widely held belief that revenue leaders have that you think is bull$*** or no longer serving us?

What You Will Learn:

• The perspectives of go-to-market leaders that are counter to many others. 

 
Host Speaker Links:
LinkedIn: www.linkedin.com/in/ssbarker
Newsletter: thegtmnewsletter.substack.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.

We have a very special episode this week. 

At the end of every weekly podcast episode, host Scott Barker asks guests the same two questions. 

Today, you’ll hear the compilation of their responses to one of the questions. 

Spoiler alert: you’ll get to tune into the other question next week, which is slightly spicier as it’s full of hot takes. 

What You Will Learn:

• What’s working and learnings for these go-to-market leaders. 
• The questions that 50+ go-to-market leaders answer in this episode: 
  1. What’s one tactic or strategy that’s working for you or the companies that you’re serving?
  2. If you can sum up your learnings in a few sentences, whether it’s something discussed on the podcast or general learnings you would want to impart in folks, what would those sentences be?

Highlights:
(2:36) The first question above. 

(25:50) The adaptation to the question, which is question #2 above.

Host Speaker Links:
LinkedIn: www.linkedin.com/in/ssbarker
Newsletter: thegtmnewsletter.substack.com

Sponsor:
Today’s episode is sponsored by Demandbase, Demandbase helps B2B companies hit their revenue goals using fewer resources. How? By using the power of AI to identify and engage the accounts and buying groups most likely to purchase. They combine your sales and marketing data with our validated B2B data and AI to create Account Intelligence that informs every step of your buyer’s journey. They deliver accurate company, contact, technographic, engagement, and intent data right where you work every day – CRM, collaboration tools, browsers, and more. Start spotting opportunities earlier and orchestrate smarter sales and marketing motions with Demandbase. See this live in action: https://www.demandbase.com/product-tour/sales-intelligence/

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.

Daniel Weiner is a former agency executive turned Founder. He started YouShouldTalkTo in 2020 amidst the madness of the pandemic and 3 years later has turned it into a 7-figure business. He also hosts a podcast and private CMO dinners in Atlanta. Outside of work he enjoys all things food/cooking, playing basketball, and working on renovating his loft.

What You Will Learn:

• How to assess what type of external support is the best fit is for you (agency/fractional/freelancer). 
• Insight behind the story of founding a company during the 2020 pandemic. 
• Why your network is your net worth and tactics for navigating business with this philosophy. 
• Advice for posting on LinkedIn consistently. 
• A playbook for vetting agencies upfront andmaking process as efficient as possible.

Highlights:
(3:18) Starting with a strong foundation in order to partner with external support. 

(4:43) The danger of asking peers which agencies / fractional / freelancer partners they work with.

(18:39) The two biggest mistakes that brands make.

(22:22) The use case for fractional work compared to agency work.

(28:04) Daniel's journey starting YouShouldTalkTo, which began in 2020. 

(34:16) The biggest lesson learned in growing his business.

(36:18) Advice for posting on LinkedIn, derived from three years of putting out content.

(40:46) Tactical advice for vetting agencies upfront and how to make the process as efficient as possible.

(48:16) One thing revenue leaders believe to be true that Daniel thinks is bull$***.

(50:00) One thing that is working for Daniel in go-to-market right now. 

Guest Speaker Link:
LinkedIn: www.linkedin.com/in/danielweiner
Podcast: podcast.youshouldtalkto.com
Website: www.youshouldtalkto.com

Host Speaker Links:
LinkedIn: www.linkedin.com/in/sophiebuonassisi
Newsletter: thegtmnewsletter.substack.com

Sponsor:
Today’s episode is sponsored by Flex, a finance super app built around a credit card with unique Net-60 day terms that enables businesses to make an investment today and pay it back 60 days later with zero percent interest. If your business growth is constrained by the cashflow you need for inventory, advertising, or something else, Flex could provide you with an interesting growth lever.

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.

May Habib is CEO and Co-Founder of Writer, the full-stack generative AI platform for enterprises. Writer empowers your entire organization to accelerate growth, increase productivity, and ensure compliance. 

May has worked in NLP and ML for 10 years, and before Writer, she founded and built Qordoba, a localization software company. She is an expert in AI-driven language generation, AI-related organizational change, and the evolving ways we use language online.

She sits on the board of TechWadi, an organization that bridges MENA-based entrepreneurs with Silicon Valley-based VC and talent networks, and is a MELI Fellow with the Aspen Institute.

May graduated from Harvard University and spends her time between San Francisco, where Writer is based, and London, where her two children live.

What You Will Learn:

• May's perspective on the economy now compared to that of 2008/2009. 
• Writer's decision to make PLG table stakes and how they leverage their motion to secure enterprise customers. 
• AI use cases - what they are and how they continue to progress. 
• Tips for recruiting the best possible team members and how patience factors into that. 
• Career insight from years of operating. 

Highlights:
(6:12) May’s learnings from Lehman Brothers and the economic crisis of 2008/2009.

(14:11) How much attention the average business leader should spend thinking about AI and how much of a near-term impact AI will have.  

(25:17) Writer's PLG motion, including self-serve and sales-assisted, and how it's used to turn small downloads into big enterprise accounts.

(31:07) A consultative sales process and messaging considerations. 

(36:56) May's strategy for recruiting A players. 

(42:55) Personal career learnings distilled by May.

Guest Speaker Link:
LinkedIn: https://www.linkedin.com/in/may-habib/

Host Speaker Links:
LinkedIn: www.linkedin.com/in/ssbarker/
Newsletter: thegtmnewsletter.substack.com/

Sponsor:
Today’s episode is sponsored by Flex, a finance super app built around a credit card with unique Net-60 day terms that enables businesses to make an investment today and pay it back 60 days later with zero percent interest. If your business growth is constrained by the cashflow you need for inventory, advertising, or something else, Flex could provide you with an interesting growth lever.

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.