Welcome to In Depth, a podcast from The First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. Hosted by Brett Berson, a partner at First Round, In Depth will cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found. We hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com
Site
RSS
Apple
Data updated on 31/08/2026
Recent rankings
Latest chart positions across Apple Podcasts and Spotify rankings.
Shared links between episodes and podcasts
Links found in episode descriptions and other podcasts that share them.
The fastest way to learn is to run two competing bets | Jay Parikh (EVP CoreAI, Microsoft)
Thursday, August 27, 2026 • Duration 01:02:29
In the latest episode of Executive Function, Brett sits down with Jay Parikh, Executive Vice President of CoreAI at Microsoft. Before joining Microsoft, Jay spent over a decade as Facebook's global head of engineering, scaling the company from a few hundred engineers to billions of users, then ran the cybersecurity company Lacework as CEO through its acquisition by Fortinet. In this conversation, he breaks down the five ingredients of great engineering leadership, discusses why he'd rather run two competing bets in parallel than forecast a winner, and explains why company culture remains more important than ever for teams to get right.
In today's episode, we discuss:
The five ingredients that separate excellent engineering leadership from the rest
How to protect your team from large shifts in public perception
The mindset shift organizations need to maintain speed at scale
How every layer of the organization needs to stay connected to the customer
Why Jay runs "brain trusts" of senior ICs with zero managers in the room
References
Akamai: https://www.akamai.com/
AWS: https://aws.amazon.com/
Facebook: https://www.facebook.com/
George Conrades: https://www.linkedin.com/in/georgeconrades/
Mark Zuckerberg: https://x.com/finkd
Microsoft: https://www.microsoft.com/
Paul Sagan: https://www.linkedin.com/in/paul-sagan-59654a1/
Tom Leighton: https://www.linkedin.com/in/tleighton/
Where to find Jay
LinkedIn: https://www.linkedin.com/in/jayparikh/
Twitter/X: https://x.com/jayparikh
Where to find Brett
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
Where to find First Round Capital
Website: https://firstround.com/
First Round Review: https://review.firstround.com/
Twitter/X: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast
Timestamps
00:00 Introduction
00:36 How leadership changes through exponential growth
02:21 The five ingredients that define excellent engineering leadership
07:51 What actually drives culture at a company as it scales
12:05 The physics behind why everything slows down at scale
18:57 The fastest team of Jay's career, and why size mattered
22:44 Why every team should think like an FDE
26:20 Managing a team through wild swings in public perception
29:07 What's different about leading through the steepest S-curve moments
33:58 Why onboarding well means going slow to go fast
37:41 Is AI actually new, or is history just repeating?
41:35 What actually counts as a "big bet" worth taking
45:01 The concrete big bets that reshaped Facebook's entire technology stack
47:35 Why vertical integration keeps being the right call as companies scale
51:46 How being a startup CEO reshaped Jay as a leader
1:01:26 Why Jay overruled Zuckerberg's instinct to skip efficiency
What startups get wrong about enterprise | Lindsey Scrase (COO, Checkr)
Thursday, July 30, 2026 • Duration 01:08:12
In the latest episode of Executive Function, Brett sits down with Lindsey Scrase, COO of Checkr. Before joining Checkr as CRO and later stepping into the COO seat, Lindsey spent nearly a decade at Google Cloud as global managing director for SMB, mid-market, and startups. In this conversation, she breaks down why moving upmarket into enterprise trips up so many startups looking to scale, how Checkr rebuilt its sales compensation model to keep pace with growth, and where AI is already reshaping her operations and go-to-market teams.
In today's episode, we discuss:
Why operators who thrive at massive-scale companies often struggle when they join a startup
The hard-won lessons from Checkr's early enterprise push that nearly failed
Why Checkr’s C-suite meets every morning with no specific agenda
The surprising challenges moving from CRO to COO
How Checkr turned AI experiments into operating systems
References
Amazon: https://www.amazon.com
Checkr: https://checkr.com
Claude: https://claude.com
Daniel Yanisse: https://www.linkedin.com/in/yanisse/
DoorDash: https://www.doordash.com
Google: https://www.google.com
Lovable: https://lovable.dev
Microsoft: https://www.microsoft.com
Where to find Lindsey
LinkedIn: https://www.linkedin.com/in/lindsey-scrase-0702442/
Twitter/X: https://twitter.com/Lscrase
Where to find Brett
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
Where to find First Round Capital
Website: https://firstround.com/
First Round Review: https://review.firstround.com/
Twitter/X: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast
Timestamps
00:00 Introduction
00:06 Why big-company executives often struggle in startups
02:18 What Checkr's first CRO needed to accomplish
03:33 How to take on an entrenched category leader
06:58 Why leaders underestimate how hard the jump to enterprise really is
10:23 Separating a true deal-blocker from a customer's nice-to-have request
18:30 Why Lindsey hired enterprise-scarred sales leader over a market leader's résumé
22:08 The biggest challenges of moving from CRO to COO
28:03 Why Checkr names a single decision-maker for every major decision
34:42 Why Checkr rebuilt their sales compensation model
40:39 What actually separates a team's best seller from everyone else
45:03 Inside Checkr’s daily, no-agenda, c-suite meeting
50:23 How following data can sometimes lead you in the wrong direction
57:27 Why hitting 130% of a goal isn’t always a good thing
58:57 Where AI has changed how Checkr's teams operate day to day
1:04:33 Advice for all aspiring COOs
How Gamma pulled off their AI pivot | Jon Noronha (Co-founder and CPO of Gamma)
Friday, July 24, 2026 • Duration 01:02:51
In this episode of In Depth, Brett sits down with Jon Noronha, co-founder and CPO of Gamma, the AI-native presentation platform used by more than 100 million people. In this conversation, he walks through Gamma’s distinct eras of product-market fit: from a pre-AI struggle with a year of runway left, to an overnight AI-fueled explosion, to today’s unplanned scramble into enterprise sales. Jon also unpacks his hard-won lessons on horizontal versus vertical bets, monetizing AI products, and why nailing onboarding turned out to be the whole game.
In today's episode, we discuss:
Why Gamma's all-in AI launch in March 2023 saved their startup
How fixing a simple onboarding problem accidentally uncovered Gamma’s entire product-market fit
Why Jon bet Gamma on a horizontal product against the advice of nearly every investor
How Gamma's daily signups climbed from hundreds to over 100,000 with zero paid marketing
What building three pricing tiers taught Jon about monetizing AI
References
Canva: https://www.canva.com/
Corgi: https://www.corgi.insure/
Facebook: https://www.facebook.com/
Gamma: https://gamma.app/
Google: https://www.google.com/
Linear: https://linear.app/
Loom: https://www.loom.com/
Microsoft: https://www.microsoft.com/
Notion: https://www.notion.com/
Optimizely: https://www.optimizely.com/
Salesforce: https://www.salesforce.com/
Slack: https://slack.com/
Zoom: https://www.zoom.us/
Where to find Jon Noronha
LinkedIn: https://www.linkedin.com/in/jonnoronha/
Twitter/X: https://twitter.com/thatsjonsense
Where to find Brett
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
Where to find First Round Capital
Website: https://firstround.com/
First Round Review: https://review.firstround.com/
Twitter/X: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast
Timestamps:
00:00 Introduction
01:47 Gamma’s three-era journey to product-market fit
03:41 Spotting the blank page problem pre-ChatGPT
05:11 How Gamma survived with only one year of runway
07:17 How onboarding fixes revealed the whole product
09:31 Choosing horizontal over investors' vertical playbook
13:41 Prototyping by hand before AI coding
15:36 How Gamma builds with future models in mind
20:06 The Kool-Aid mistake of a late PowerPoint export
24:31 Why the presentation industry hadn't evolved since 1987
33:30 How Gamma solves evals for taste, not just data
40:21 Jon's hardest lessons monetizing AI since 2023
44:16 The fast leap from prosumer to enterprise
47:01 Why product still beats distribution
52:06 The metric that proved product-market fit
57:36 Pricing advice for prosumer AI founders
59:01 The toils and realities of founder life
Why Plaid’s COO cold-calls new hires | Eric Sager (COO of Plaid)
Thursday, July 16, 2026 • Duration 01:09:04
In the latest episode of Executive Function, Brett sits down with Eric Sager, COO of Plaid, following stints as CRO of Bluevine and Head of Sales at Square. During his seven-year tenure at Plaid, Eric has helped lead the business through a pandemic, Visa's collapsed acquisition, a fintech downturn, and the AI boom. In today’s conversation, he unpacks how he kept teams focused during turbulent times, why he refuses to run at 100% capacity, and how he re-architected the go-to-market function as Plaid scaled.
In today's episode, we discuss:
How Plaid stayed focused after the Visa acquisition fell through and then raised at nearly 3x the price
Why great COOs deliberately make themselves obsolete
Why Eric treats speed, risk, and cost as a three-way trade-off, and why sometimes going slower wins
How refusing to run at 100% capacity helped Plaid win OpenAI, Perplexity, and Replit
Why Eric personally cold-calls brand-new employees
References
Bain & Company: https://www.bain.com
Bluevine: https://www.bluevine.com
Chase: https://www.chase.com
Citibank: https://www.citi.com
Eyal Lifshitz: https://www.linkedin.com/in/eyallifshitz/
Françoise Brougher: https://x.com/FrancoiseBr
Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1/
Jack Dorsey: https://x.com/jack
Michael Mankins: https://www.linkedin.com/in/michaelcmankins
OpenAI: https://openai.com
Perplexity: https://www.perplexity.ai
Plaid: https://plaid.com
Replit: https://replit.com
Sarah Friar: https://www.linkedin.com/in/sarah-friar/
Square: https://squareup.com
Visa: https://www.visa.com
William Hockey: https://www.linkedin.com/in/william-hockey-04536710
Zach Perret: https://www.linkedin.com/in/zperret/
Where to find Eric Sager
LinkedIn: https://www.linkedin.com/in/eric-sager-a529516
Where to find Brett
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
Where to find First Round Capital
Website: https://firstround.com/
First Round Review: https://review.firstround.com/
Twitter/X: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast
Timestamps
00:00 Introduction
00:40 Leading a company through turbulent times
04:24 How to build a resilient team culture
08:33 How Plaid avoids bureaucracy, while operating at scale
10:58 The speed-quality tradeoff: Going faster isn't always better
15:32 When to move from generalists to specialized customer segments
20:14 Why Plaid has one owner for entire customer relationships
22:06 The "quarterback" model: one owner, experts on call
24:08 Why you should never run your org at 100% capacity
29:47 "Always available, never needed": the support mantra
36:49 Eric’s unusual "hit by a bus" test to measure job success
43:57 Why Eric cold calls brand-new employees
52:14 Eric's week: 25% ecosystem, 50% business, 25% team
55:15 How to spot fake mission alignment in interviews
59:04 The one thing a founder has that no hire can replicate
How Supabase became the essential infrastructure for the AI era | Paul Copplestone (Co-founder, CEO)
Thursday, June 25, 2026 • Duration 59:53
In this episode of In Depth, Brett sits down with Paul Copplestone, co-founder and CEO of Supabase, the open-source Postgres platform now serving more than seven million developers. Before Supabase, Paul launched a Thumbtack-style marketplace in Southeast Asia and co-founded an office-management startup called Nimbus, experiences that taught him to separate fundraising from building and to find product-market fit before blitzscaling. He breaks down how a single tagline change for Supabase unlocked product-market fit, why he runs a fully distributed async team with near-zero attrition, and how he turned PLG signals into a product-led sales motion comped only on incremental uplift.
In today's episode, we discuss:
How changing one tagline helped Supabase go to #1 in Hacker News - an early sign of product market fit
Why Paul ran Supabase like it had only $100K in the bank despite raising real money
How Supabase rode three distinct AI waves, from pgvector to Bolt and Lovable, to Claude Code
Why Supabase built a sales team comped only on the incremental uplift over a control group
What the Toyota production system's "kaizen" taught Paul about unblocking a scaling team
References:
Ant Wilson: https://www.linkedin.com/in/ant-wilson-46179937
Bolt: https://bolt.new/
Claude Code: https://www.anthropic.com/claude-code
Codex: https://openai.com/codex/
Entrepreneurs First: https://www.joinef.com/
Firebase: https://firebase.google.com/
Lovable: https://lovable.dev/
MongoDB: https://www.mongodb.com/
Next.js: https://nextjs.org/
PostgreSQL: https://www.postgresql.org/
Supabase: https://supabase.com/
Thumbtack: https://www.thumbtack.com/
Y Combinator: https://www.ycombinator.com/
Where to find Paul:
LinkedIn: https://www.linkedin.com/in/paulcopplestone
Twitter/X: https://x.com/kiwicopple
Where to find Brett:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
Where to find First Round Capital:
Website: https://firstround.com/
First Round Review: https://review.firstround.com/
Twitter/X: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast
Timestamps:
00:00 Introduction
01:32 Why Paul's earlier startups were never destined to be huge
07:14 Unlearning the "tall poppy" mindset and going all-in on async
09:54 Reverse-engineering why Supabase was an outstanding idea
12:04 The accidental Hacker News launch and tagline lesson
13:58 Where the early roadmap came from: demand vs. technical taste
17:28 Skill vs. luck, and operating like you have $100K in the bank
21:42 What actually makes a great developer experience
23:10 Solving the "graduation problem" Firebase never could
24:58 The role of open source in Supabase's success
26:10 The three distinct AI tailwinds: From pgvector to Claude Code
35:24 Supabase’s egoless, hyper-competitive open-source culture
42:58 A tactical playbook for raising capital
48:37 Product-led sales comped on incremental uplift only
59:27 The production philosophy behind Supabase’s operations
How to build a beloved tech brand | Sheila Joglekar Vashee (CMO, Figma)
Thursday, June 4, 2026 • Duration 01:00:48
In today's conversation, Brett sits down with CMO of Figma, Sheila Joglekar Vashee. Previously the second marketing hire at Dropbox, where she helped scale the company past $1 billion in revenue, she now leads marketing at Figma fresh off its IPO. In an industry that has spent a decade trying to turn marketing into something closer to hedge fund trading, Sheila argues the art was always the point — we just stopped talking about it. She unpacks how to run marketing as a portfolio of moonshots, why giving teams different goals breeds dysfunction, how to scale taste across an organization, and why old playbooks are obsolete, even as the fundamentals hold.
In today's episode, we discuss:
How to run marketing like a portfolio of moonshots
The value of disruptive energy for senior marketers
Why "Ubiquity is the opposite of cool"
How to actually scale taste across an organization
What great marketing looks like in the AI era
Referenced:
Apple: https://www.apple.com/
Dennis Woodside: https://www.linkedin.com/in/dennis-woodside-341302/
Dropbox: https://www.dropbox.com/
Dylan Field: https://www.linkedin.com/in/dylanfield/
Figma: https://www.figma.com
Francoise Brougher: https://www.linkedin.com/in/francoise-brougher-341a72/
Gap: https://www.gap.com/
Google Chrome: https://www.google.com/chrome/
Harley-Davidson: https://www.harley-davidson.com/
HubSpot: https://www.hubspot.com/
Notion: https://www.notion.com/
Opendoor: https://www.opendoor.com/
Pinterest: https://www.pinterest.com/
Square: https://squareup.com/
The Web Is What You Make of It (Dear Sophie): https://www.youtube.com/watch?v=pzOBOuyr-EU
Urban Outfitters: https://www.urbanoutfitters.com/
Yamini Rangan: https://www.linkedin.com/in/yaminirangan/
Where to find Sheila:
LinkedIn: https://www.linkedin.com/in/sheilavashee/
X: https://x.com/sheilavashee
Where to find Brett:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986644/
X: https://x.com/brettberson
Where to find First Round Capital:
Website: https://firstround.com/
First Round Review: https://review.firstround.com/
Twitter/X: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast
Timestamps:
00:00 Introduction
00:07 What excellent marketing actually is in 2026
01:36 Why giving teams different goals creates dysfunction
02:36 The most important decision Sheila made as CMO last year
04:26 The real difference between an SVP and a CMO
06:05 Marketing is one engine - not separate pieces
07:15 The tension between brand and growth
09:25 The decisions a CMO should never be making
09:55 Running marketing like a portfolio of moonshots
12:46 "Ubiquity is the opposite of cool"
15:11 Why a few companies get a flywheel of momentum
16:44 The Silicon Valley clock and irrational perception cycles
19:25 How to actually scale taste across an org
21:09 What changes for a CMO in a post-LLM world
23:15 Why the artistic side of marketing never really left
26:05 Whether taste can ever be encoded in software
27:15 Telling an optimistic, yet realistic story about AI
30:50 You need to make people care
32:11 What surprised Sheila about being a public-company CMO
33:46 Why Figma won enterprise where Dropbox couldn't
35:25 Sheila’s favorite campaign ever
37:10 Why announcement videos full of humans, lack humanity
38:55 Playbooks are obselete, but the fundamentals are not
40:25 Why marketing in 2026 demands disruptive energy
41:54 How Sheila architects her week
48:55 Where corporate politics actually come from
53:55 "Sheila, are you going to change the world in this job?"
58:09 What's unique about the CMO and CEO relationship
Why old-school sales work still wins in the AI era | Graham Moreno (Head of GTM, Parallel)
Thursday, May 21, 2026 • Duration 01:02:13
In the latest episode of Executive Function, Brett sits down with Graham Moreno, Head of GTM at Parallel Web Systems. Before Parallel, Graham scaled Windsurf's GTM organization from three sellers to seventy-five in under a year, served as President through the Cognition acquisition, and earlier built and led enterprise sales teams at Grafana Labs and MongoDB. In this conversation, he unpacks why the AI-era backlash against structured enterprise sales misreads the data, how to design a process that raises the floor for ordinary reps without capping the ceiling for stars, and why selling to AI-native customers compresses an eight-week cycle into five business days.
In today's episode, we discuss:
Why in-person enterprise rollouts still beat product-led motions
Building a robust sales process that still leaves room for unscripted moments
Why the three highest-leverage early sales hires aren't sellers at all
The case for outsized commission accelerators for star sellers — and the kind of person they attract
Why most AI companies are skipping the in-person sales work that enterprise customers actually want
References:
Ahead: https://www.ahead.com
Amazon: https://www.amazon.com
Anthropic: https://www.anthropic.com
Attio: https://www.attio.com
Augment Code: https://www.augmentcode.com/
Cognition: https://cognition.ai
Cursor: https://cursor.com
Dani McCabe: https://www.linkedin.com/in/danielle-mccabe/
Datadog: https://www.datadoghq.com
GitHub Copilot: https://github.com/features/copilot
HubSpot: https://www.hubspot.com
Jeremy Powers: https://www.linkedin.com/in/jeremypowers/
JPMorgan: https://www.jpmorgan.com
Matt McClernan: https://www.linkedin.com/in/mattmcclernan/
MongoDB: https://www.mongodb.com
Nicole Rettinger: https://www.linkedin.com/in/nicole-rettinger-23b20465/
Notion: https://www.notion.com
OpenAI: https://openai.com
Parag Agrawal: https://www.linkedin.com/in/paragagr/
Parallel: https://parallel.ai
Snowflake: https://www.snowflake.com
University of Chicago: https://www.uchicago.edu
Windsurf: https://windsurf.com
Where to find Graham:
LinkedIn: https://www.linkedin.com/in/grahammoreno/
Where to find Brett:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
Where to find First Round Capital:
Website: https://firstround.com/
First Round Review: https://review.firstround.com/
Twitter/X: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast
Timestamps:
00:00 Introduction
00:32 Has the sales playbook changed in the AI era?
02:13 Why "showing up" beats letting the marketplace decide
06:50 Why great salespeople sell to engineers and executives in one motion
11:37 Selling to AI-native buyers who grew up on ChatGPT
13:49 Same seller, different tempo: 8 weeks vs. 8 business days
15:57 How AI-native buyers handle build vs. buy decisions
17:48 The rep who taught a champion's son guitar over Zoom
19:03 Raising the floor without capping the ceiling
22:09 Why too much process narrows the kind of seller you attract
25:46 The three pillars of GTM excellence
31:00 Building peers who are 80% aligned, not 100%
38:03 Whether AI is changing what good enablement looks like
41:35 Selling against direct and implied competitors at once
42:45 Instrumenting the funnel from stage zero to close
45:57 Why post-sales should always roll up to the revenue leader
48:19 The case for outsized commissions
52:02 The 96 hours of panic before Cognition acquired Windsurf
53:04 How far out should a GTM leader be planning?
57:53 What a normal week looks like in hypergrowth
Why founders should bet on first-time executives | Praveer Melwani (CFO, Figma)
Thursday, May 14, 2026 • Duration 43:48
In this latest episode of Executive Function, Brett sits down with Praveer Melwani, CFO at Figma. Praveer joined Figma in 2017 as the company's first business operations and finance hire—when the team was around 30 people and not yet charging for the product—and stepped into the CFO seat in 2022, helping to lead the company’s IPO in 2025. In today’s conversation, Praveer breaks down the step functions that took him from IC to CFO, why Figma started acting like a public company three years before IPO, and how AI is rewriting capital allocation and the CFO job itself.
In today's episode, we discuss:
What separates a world-class finance leader from a traffic-cop CFO
How Praveer went from Figma's first biz ops hire to CFO of a public company in nine years
Why Figma started acting like a public company three years before its IPO
What Praveer has learned working alongside Dylan Field for nine years
Why Figma intentionally cut its 90% gross margin to invest in AI
References:
Adobe: https://www.adobe.com
Brendan Mulligan: https://www.linkedin.com/in/brendanmulligan
Cloudflare: https://www.cloudflare.com
Dropbox: https://www.dropbox.com
Dylan Field: https://www.linkedin.com/in/dylanfield/
Fidelity: https://www.fidelity.com
Figma: https://www.figma.com
GIC: https://www.gic.com.sg
NerdWallet: https://www.nerdwallet.com
Shaunt Voskanian: https://www.linkedin.com/in/shauntvoskanian/
Where to find Praveer:
LinkedIn: https://www.linkedin.com/in/praveer-melwani
Where to find Brett:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
Where to find First Round Capital:
Website: https://firstround.com/
First Round Review: https://review.firstround.com/
Twitter/X: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast
Timestamps:
00:00 Introduction
02:13 From banking to Dropbox to Figma
04:14 The phase shift when Figma's COO left
05:36 Hiring leaders in functions you don't understand
07:18 Selling the exec team on AI consumption pricing
09:48 Using Claude Code to learn new things as CFO
11:36 Building an internal board of peer CFOs
13:52 Inside Figma's CFO job description
16:38 What separates good CFOs from world-class CFOs
18:42 Capital allocation and risk in a post-ChatGPT world
21:45 Why Praveer wants to take more bets
24:32 How AI is materially changing the CFO role
25:36 The nine-year working relationship with Dylan Field
29:12 How deeply in the details should a CFO be?
31:47 What Dropbox taught Praveer about building strong teams
33:24 Praveer’s first-principles test for hiring VPs
38:47 Why Figma acted like a public company in 2022
Why great product leaders should stop obsessing over the roadmap | Diya Jolly (CPO & CTO of Xero)
Thursday, April 30, 2026 • Duration 49:54
In the latest episode of Executive Function, Brett is joined by Diya Jolly, Chief Product and Technology Officer at Xero. Before Xero, Diya was CPT at Okta and led YouTube's advertising monetization products at Google. In this conversation, she unpacks her three-bucket framework for delegating decisions, why the most important part of a CPO’s role is to drive team-wide ambition, and why the best executives need to spend half their time thinking, not doing.
In today's episode, we discuss:
Why a CPO's number one job is raising their team’s ambition, not shipping features
How to demand the best from your team without creating a fear-based culture
Why organizational politics is actually an incentives problem
How Diya is “militant” with her calendar to carve out dedicated thinking time
Why you should avoid chasing titles in your career - and what to chase instead
References:
Google: https://www.google.com
Melio: https://meliopayments.com
Okta: https://www.okta.com
Sukhinder Singh Cassidy: https://www.linkedin.com/in/sukhinders/
Xero: https://www.xero.com
Where to find Diya:
LinkedIn: https://www.linkedin.com/in/diyajolly
Where to find Brett:
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
Where to find First Round Capital:
Website: https://firstround.com/
First Round Review: https://review.firstround.com/
Twitter/X: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast
Timestamps:
00:12 How an excellent CPO makes an impact on the business
02:01 How the CPO role shifts under founders vs hired CEOs
03:38 Influencing a founder without going deferential
07:37 How adding value to customers is always a net positive
08:45 Why roadmaps need more risk in the AI era
12:30 How to shelter innovation teams from the existing system
15:12 What's different about being a great CPO in 2026
17:34 How AI has changed the concept of an app
18:28 It’s essential for CPOs to fly at a low altitude
20:34 How misaligned incentives cause organizational politics
25:13 Being demanding without creating a fear-based culture
28:10 Why raising ambition is a CPO's number one job
31:39 The boss who taught Diya to keep raising the bar
32:43 The hardest part of being a CPO
35:28 The three buckets Diya uses to delegate
36:30 How Diya protects deep-work time on her calendar
42:45 Xero’s game-changing early bet on AI insights
44:58 How far into the future should CPOs plan for?
47:14 What it takes to be an excellent C-suite member
48:53 Why ambitious PMs should chase impact, not titles
50:28 The four bottlenecks that stall career growth
Inside Artemis' "AI vs AI" war | Shachar Hirshberg & Dan Shiebler (Co-founders, Artemis)
Tuesday, April 21, 2026 • Duration 56:59
In this episode of In Depth, First Round Partner Josh Kopelman sits down with Shachar Hirshberg and Dan Shiebler, co-founders of Artemis, the AI-native security platform that just emerged from stealth with $70M in combined seed and Series A funding. Shachar and Dan unpack how they built a 30-person team in seven months, why AI-native companies are outperforming their AI-enabled counterparts, and why they plan to stay on a texting basis with every customer, even at scale.
In today's episode, we discuss:
How to interview for AI fluency when building an AI-native startup
Why founder-market fit is a critical early signal for startup success
The surprising lesson Dan learned from founder-led sales
How Dan and Shachar are instilling customer-obsession into Artemis’ culture
How the two co-founders approach conflict and decision-making
References:
Abnormal: https://abnormal.ai
Amazon Web Services (AWS): https://aws.amazon.com
Anthropic: https://www.anthropic.com
Artemis: https://artemissecurity.com
CrowdStrike: https://www.crowdstrike.com
Demisto (now Cortex XSOAR): https://www.paloaltonetworks.com/cortex/cortex-xsoar
OpenAI: https://openai.com
Palo Alto Networks: https://www.paloaltonetworks.com
Todd Jackson: https://www.linkedin.com/in/toddj0/
Where to find Shachar Hirshberg:
LinkedIn: https://www.linkedin.com/in/shachar-hirshberg/
Where to find Dan Shiebler:
LinkedIn: https://www.linkedin.com/in/dan-shiebler-10219b42/
Where to find Josh:
LinkedIn: https://www.linkedin.com/in/jkopelman/
Twitter/X: https://x.com/joshk
Where to find First Round Capital:
Website: https://firstround.com/
First Round Review: https://review.firstround.com/
Twitter/X: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast
Timestamps:
00:00 Introduction
00:06 What Artemis does and why now
02:51 Shachar’s AWS and Palo Alto playbook
05:15 Dan’s founder journey: From Twitter to Abnormal
08:51 Why founder-market fit is critical for startups
11:38 Finding the right moment to take the leap and build
13:52 The hiring process that powers a startup in stealth
16:58 Building a team centered on AI capabilities
21:48 How AI implementation changes dashboard metrics
23:22 The ICP they chased and the one they ignored
26:44 The magic of closing the first customers
27:49 The surprising signals of early product-market fit
32:06 Critical lessons from founder-led sales
33:51 Why the first product should make founders uncomfortable
36:03 Hiring 30 people while still in stealth
42:08 “Should we be arguing more?”
43:37 How the AI security market is evolving
49:03 Why AI-native beats AI-enabled company structure
51:09 The most surprising moments as a first-time founder
Discover shows related to In Depth, based on actual content similarities. Explore podcasts with similar topics, themes, and formats, backed by real data.
