In Depth

In this episode of In Depth, Todd sits down with Jean-Denis Greze, co-founder and CEO of Town, the AI work assistant that gives every employee their own agent. Before Town, Jean-Denis spent seven years as CTO of Plaid and led engineering teams at Dropbox, where he and Todd first worked together. In this conversation, they dive into what it takes to build in tech's hottest category while competing with Microsoft, Google and the frontier labs, why Town bet on work agents over personal agents, and how to get agents to share the right information with each other.

In today's episode, we discuss:

•

The edge that keeps Town competitive with Google and Microsoft

•

How user feedback adjusted Town’s product

•

Why Jean-Denis believes people will start delegating decision-making to AI

•

What a multiplayer AI assistant world looks like

•

Why Town started rolling back its guardrails after users approved 95% of agent actions

References:

•

Anthropic: https://www.anthropic.com/

•

Bret Taylor: https://www.linkedin.com/in/brettaylor/

•

Dropbox: https://www.dropbox.com/

•

Facebook: https://www.facebook.com/

•

Figma: https://www.figma.com/

•

Glean: https://www.glean.com/

•

Google: https://www.google.com/

•

HubSpot: https://www.hubspot.com/

•

Instinct: https://instinct.com/

•

Meta: https://www.meta.com/

•

Microsoft: https://www.microsoft.com/

•

OpenAI: https://openai.com/

•

Plaid: https://plaid.com/

•

Salesforce: https://www.salesforce.com/

•

Sierra: https://sierra.ai/

•

Slack: https://slack.com/

•

Town: https://www.town.com/

Where to find Jean-Denis:

•

LinkedIn: https://www.linkedin.com/in/jeandenisgreze

•

Twitter/X: https://x.com/jgreze

Where to find Todd:

•

LinkedIn: https://www.linkedin.com/in/toddj0/

•

Twitter/X: https://x.com/tjack

Where to find First Round Capital:

•

Website: https://firstround.com/

•

First Round Review: https://review.firstround.com/

•

Twitter/X: https://x.com/firstround

•

YouTube: https://www.youtube.com/@FirstRoundCapital

•

This podcast on all platforms: https://review.firstround.com/podcast

Timestamps:

00:00 Introduction

01:28 Competing in the AI agent race

03:23 Why people will run two AI assistants

07:01 Why personal AI hits a ceiling and work AI doesn't

09:08 What made always-on agents possible now

15:54 Building on labs that compete with you

17:57 Pricing tokens instead of outcomes

22:52 How Town's users drive new features

25:08 Why Town is actually an AI onboarding platform

27:15 What a design-minded co-founder brings

29:13 The one-agent-per-person debate

30:59 Why Town pivoted from tax to AI assistants

32:01 Designing an agent people can trust

35:27 How multiplayer changes privacy

44:33 Why AI should choose what you share with coworkers

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

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

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

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

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

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

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

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

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

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

In this latest episode of Executive Function, Brett sits down with Christopher Payne, who spent a decade as President and COO at DoorDash, helping scale the company from roughly 70 employees to the dominant food delivery platform in the US. Before DoorDash, Christopher held senior operating roles at Amazon and eBay, where he led a sweeping overhaul of marketplace search. In this conversation, he unpacks what it actually takes to run an atoms-based business versus a software company, shares his "plate spinning" framework for allocating executive attention across a complex org, and makes the case for top-down goal setting over the bottom-up alternative.

In today's episode, we discuss:

• How prior industry experience can be a liability when you're trying to reinvent the market
• How executives can practically focus their attention to stay close to product details
• What charisma actually looks like in executives—and why it's a staple trait to have
• The business case for setting ambitious goals top-down, not bottom-up

References:

• Amazon: https://www.amazon.com/
• Anthropic: https://www.anthropic.com/
• Cheesecake Factory: https://www.thecheesecakefactory.com/
• Cursor: https://cursor.com/
• Dartmouth College: https://home.dartmouth.edu/
• David Risher: https://www.linkedin.com/in/jdavidrisher
• DoorDash: https://www.doordash.com/
• eBay: https://www.ebay.com/
• Granola: https://www.granola.ai/
• Hulu: https://www.hulu.com/
• Jason Kilar: https://www.linkedin.com/in/jasonkilar
• Jeff Bezos: https://x.com/JeffBezos
• Lyft: https://www.lyft.com/
• Microsoft: https://www.microsoft.com/
• Tinder: https://tinder.com/
• Tony Xu: https://www.linkedin.com/in/xutony
• Travis Kalanick: https://www.linkedin.com/in/traviskalanick
• Uber: https://www.uber.com/
• University of Oregon: https://www.uoregon.edu/
• Wharton School: https://www.wharton.upenn.edu/

Where to find Christopher Payne:

• LinkedIn: https://www.linkedin.com/in/christopherpayne
• Twitter/X: https://x.com/chrispa

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

00:14 Why atoms businesses challenge bits executives

02:35 Hiring executives with a builder mentality

06:52 Great executives never outgrow the details

08:05 How ciabatta bread revealed a core DoorDash issue

10:48 How executives can scale their own impact

14:22 One-size-fits-all management is a myth

19:01 Enduring business lessons from Jeff Bezos

20:56 “I was fired from Tinder after six months”

25:38 Why specializing too early is a leadership trap

27:41 Are competitive cultures essential for success?

31:00 Lessons from Amazon’s hypergrowth

35:20 Why having industry experience can be a liability

38:46 Companies spend too much time on job interviews

40:19 The skills executives need for hypergrowth

43:34 Why AI will likely flatten organizations

45:20 Teaching COO 101: What it takes to be world-class

50:55 Why bottom-up goal setting kills ambition

55:29 How charismatic leaders help teams in tough times

58:23 The number-one sign of high-functioning executive teams

1:02:02 How first-time COOs can increase their chance of success

In the latest episode of Executive Function, Brett sits down with Katie Burke, who recently became COO of Harvey after joining as Chief People Officer. Before Harvey, Katie spent 11 years in HR leadership at HubSpot, where she built one of tech's most distinctive cultures. In this conversation, she unpacks her marketing-minded approach to HR, why she hired deliberately from hospitality rather than corporate backgrounds, and why developing culture should be a strategic priority for any organization.

In today's episode, we discuss:

• Why HR leaders should think like marketers
• The 2.5-year cultural hangover after a layoff
• The protein vs. sugar rule for employee feedback
• What it means to be the executive team’s own HR business partner
• What the Chief People Officer owes the board and what they don't

References:

• Amazon: https://www.amazon.com
• Anique Drumright: https://www.linkedin.com/in/anique-drumright-53978a1a/
• Brian Halligan: https://www.linkedin.com/in/brianhalligan/
• Carmel Galvin: https://www.linkedin.com/in/carmelgalvin/
• eBay: https://www.ebay.com
• Gabe Pereyra: https://www.linkedin.com/in/gabepereyra
• Harvey: https://www.harvey.ai
• HubSpot: https://www.hubspot.com
• Jacqui Canney: https://www.linkedin.com/in/jacquicanney
• Klaviyo: https://www.klaviyo.com
• Lorrie Norrington: https://www.linkedin.com/in/lorrienorrington/
• Maggie Landers: https://www.linkedin.com/in/maggiecohenlanders/
• Rippling: https://www.rippling.com
• ServiceNow: https://www.servicenow.com
• Winston Weinberg: https://www.linkedin.com/in/winston-weinberg/

Where to find Katie:

• LinkedIn: https://www.linkedin.com/in/katie-burke-965767a/
• Twitter/X: https://x.com/katieburkie

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

00:23 Why HR begins with thinking like a marketer

01:58 “Don't ask for a seat at the table. Build the table.”

02:29 Radical transparency after Hubspot’s IPO

05:14 How HubSpot’s people function drove strategy

07:01 The trickiest part of the Chief People Officer role

10:00 Be the Michael Jordan of your exec team

12:14 Why people leaders need to create “graceful exits”

16:49 The inevitable two-year layoff hangover

23:31 The workplace shouldn’t be Disneyland

26:05 “Our job is not to make you happy every day”

34:28 Being a Chief People Officer isn’t for the faint of heart

35:04 How “Berry-Gate” taught HubSpot to manage feedback

40:51 Chief People Officers should be demanding, by design

42:01 Why “frequent flyers” are a new-hire red flag

44:54 Unpacking the role of the VP of People

49:94 Which company decisions fall to the Chief People Officer?

49:11 The most common challenges of scaling a company

51:39 The differences between HubSpot and Harvey

53:17 How AI is changing the people function

1:04:28 Why Katie shares her own performance reviews

1:06:22 How to manage a disagreement with the CEO

Jay Kreps is the co-founder and CEO of Confluent, the company built around Apache Kafka — the open-source data streaming platform he originally built while at LinkedIn. In this conversation, Jay shares his full journey: how Confluent grew from a scrappy group of engineers with no go-to-market experience into a publicly traded enterprise software company. He makes the case that the difference between what a company can do, and what it must do, is one of the most underrated building levers; illustrated through his years spent pushing Confluent towards a cloud product, in the face of widespread opposition.

In this episode, we discuss:

• Why moving from software engineer to CEO requires almost an entirely new skillset
• The product marketing pyramid Jay built to explain Kafka to the world
• How Confluent bludgeoned its way to a cloud-first business when the early product was “embarrassing”
• The critical difference between what a company can do and what it must do
• What keeps scaling companies from becoming "Chipotle”

References:

• Amazon Web Services: https://aws.amazon.com/
• Apache Kafka: https://kafka.apache.org/
• Benchmark: https://www.benchmark.com/
• Confluent: https://www.confluent.io/
• Jun Rao: https://www.linkedin.com/in/junrao
• LinkedIn: https://www.linkedin.com/
• McKinsey & Company: https://www.mckinsey.com/
• MySpace: https://www.myspace.com/
• Neha Narkhede: https://www.linkedin.com/in/nehanarkhede
• Oracle: https://www.oracle.com/
• Red Hat: https://www.redhat.com/
• Snowflake: https://www.snowflake.com/

Where to find Jay:

• LinkedIn: https://www.linkedin.com/in/jaykreps/
• Twitter/X: https://x.com/jaykreps

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:

01:18 Making the leap from engineer to CEO

03:33 The 80% rule: what a CEO actually needs to know

04:54 Scaling different business disciplines

09:31 How Confluent’s story began in LinkedIn

12:13 The growing need for scalable data tech

13:37 What the early Kafka product looked like

16:38 Kafka’s underwhelming open-source launch

18:38 The blog post that accelerated Kafka’s adoption

20:16 Why so many marketing messages fail

28:08 The decision to build Confluent

34:24 Planning to fundraise before building the product

39:19 Confluent’s early years: Tough product decisions

47:07 The underrated growth lever question for companies

55:46 Why founder optimism is an overrated trait

1:00:29 What should founders give up as they scale?

1:02:47 Why people become trapped in a failure mindset

1:08:33 The Chipotle problem: Losing excellence at scale

In the latest episode of Executive Function, Brett is joined by Jeremy Epling, CPO of security and compliance platform Vanta. Jeremy details his career journey, unpacking what it took to make the jump from tenured Microsoft executive to startup CPO. He also shares hard-won insights: how to maintain shipping velocity as headcount explodes, how to manage performance without the safety net of big-company process, and what it means to run a product org where the buck truly stops with you.

In today's episode, we discuss:

• The mindset shift that made Jeremy's transition to startup CPO work
• Why it’s essential for the CPO to stay connected to details
• The rule to ensure teams ship fast while growing quickly
• Why rigid hierarchies derail quality decision-making
• How Jeremy uses open office hours for the entire company

References:

• Christina Cacioppo: https://www.linkedin.com/in/ccacioppo/
• Dropbox: https://www.dropbox.com
• GitHub: https://www.github.com
• Ironclad: https://www.ironcladapp.com
• Jensen Huang: https://www.linkedin.com/in/jenhsunhuang/
• Lovable: https://lovable.dev
• Microsoft: https://www.microsoft.com
• Nat Friedman: https://www.linkedin.com/in/natfriedman/
• NVIDIA: https://www.nvidia.com
• Span: https://www.span.app/
• v0: https://v0.dev
• Vanta: https://www.vanta.com

Where to find Jeremy:

• LinkedIn: https://www.linkedin.com/in/jeremy-epling-j40/
• Twitter/X: https://x.com/jeremy_epling

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

00:09 Why most big-tech executives fail at startups

05:38 Great product leaders stay in the details

09:21 The biggest mindset shift from VP to CPO

16:24 Revenue and product teams are always at odds

18:00 The key to a quality CPO and CRO relationship

23:21 Stop making your team fetch rocks

25:54 Who ultimately oversees the quality bar?

32:27 Why rigid hierarchies kill great companies

36:38 How to leave actionable, detailed feedback

38:55 Great CPOs should avoid comfort metrics

47:27 A glimpse into Jeremy’s working week

49:07 The case for weekly 1:1s

55:13 Why ICs are the unsung heroes of a company

58:25 Jeremy’s most formative career moments

1:07:55 The hardest skills Jeremy had to learn

1:09:31 Why great managers know when to push

Keller Cliffton is the co-founder and CEO of Zipline, the world's largest commercial autonomous delivery system, which today serves 5,000 hospitals across multiple countries and saves an estimated 17,000 lives per year. In this episode, Keller breaks down his extreme hiring philosophy that has powered Zipline for over a decade. He also walks through Zipline’s full origin story: from a near-dead home robot startup to a scrappy bet on drone blood delivery in Rwanda, to 135 million autonomous miles flown.

In today's episode, we discuss:

• Why Zipline hires teenagers over PhDs
• Why the best startup employees are "heat-seeking missiles for pain"
• The 5 leadership attributes Zipline has never shared publicly
• The brutal firing advice that shaped Keller’s leadership
• How Rwanda’s health minister changed Zipline’s trajectory

References:

• Airbnb: https://www.airbnb.com
• Alfred Lin: https://www.linkedin.com/in/linalfred/
• Amazon: https://www.amazon.com
• Apple: https://www.apple.com
• Brian Chesky: https://www.linkedin.com/in/brianchesky/
• Cleveland Clinic: https://my.clevelandclinic.org
• Netflix: https://www.netflix.com
• Paul Kagame: https://www.linkedin.com/in/paulkagame/
• Reflect Orbital: https://www.reflectorbital.com
• Sequoia Capital: https://www.sequoiacapital.com
• SpaceX: https://www.spacex.com
• Sphero: https://www.sphero.com
• Tesla: https://www.tesla.com
• University of Washington: https://www.washington.edu
• Walmart: https://www.walmart.com
• Zipline: https://www.zipline.com

Where to find Keller:

• LinkedIn: https://www.linkedin.com/in/kellerrc/
• Twitter/X: https://x.com/Keller

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

02:11 Why Zipline doesn't hire for experience

06:04 Are founders born or made?

07:37 Why Zipline hires 17-year-olds over PhDs

17:03 The employees Zipline doesn't want

18:53 The ultimate startup hire is a "heat-seeking missile"

20:36 Why blind references are a non-negotiable

23:07 Can candidates admit when they screwed up?

30:10 Zipline's secret leadership playbook

35:16 Why you should always fire quickly

36:26 The early vision for Zipline

39:48 How Zipline almost died - twice

44:55 From toy robots to drone delivery: Zipline's pivot

51:35 How Rwanda's health minister changed everything

57:10 Why Zipline's launch was a "complete disaster"

1:04:05 Scaling from 1 hospital to 5000

1:05:17 The 10x hardware cost rule every founder should know

Chris Degnan was the first sales hire at Snowflake and spent 11 years scaling the company from zero to $3.5 billion in revenue as its CRO, working alongside four different CEOs and learning from each one. In this episode, Chris breaks down what it actually takes to scale an enterprise sales organization, why MEDDIC is the methodology every founder should know, and what working under Frank Slootman taught him about firing fast, taking feedback and finding the fakers in your team.

In today's episode, we discuss:

• What the CRO job looks like at $10M vs. $1B+
• Why sales leaders must know how to sell the product themselves
• The MEDDIC methodology and why it's a founder's best insurance policy
• How to find the fakers, manage-uppers and passengers in your org
• What Frank Slootman got right — and wrong — about scaling Snowflake
• Why most AI companies will face a go-to-market reckoning

References:

• Amazon: https://www.amazon.com/
• Bob Muglia: https://www.linkedin.com/in/bob-muglia-714ba592/
• Carl Eschenbach: https://www.linkedin.com/in/carl-eschenbach-980543/
• Christian Kleinerman: https://www.linkedin.com/in/christian-kleinerman-a973102/
• Denise Persson: https://www.linkedin.com/in/denisepersson/
• Dell: https://www.dell.com/
• Frank Slootman: https://www.linkedin.com/in/frankslootman/
• John McMahon: https://www.linkedin.com/in/johnmcmahon1/
• Michael Scarpelli: https://www.linkedin.com/in/michael-scarpelli-1b289b9/
• Microsoft: https://www.microsoft.com/
• Oracle: https://www.oracle.com/
• Salesforce: https://www.salesforce.com/
• Snowflake: https://www.snowflake.com/
• Sridhar Ramaswamy: https://www.linkedin.com/in/sridhar-ramaswamy/
• Stanford Graduate School of Business: https://www.gsb.stanford.edu/

Where to find Chris:

• LinkedIn: https://www.linkedin.com/in/chris-degnan/

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 What is the job of a CRO?

01:12 What excellence looks like at different revenue stages

02:59 Sales leaders need to know how to sell the product

04:52 The hardest skill leaders have to learn

08:17 You need to stay open to feedback - at all levels

14:01 Sales, segmentation, and international expansion

16:17 Why MEDDIC is the foundation for every sales org

20:32 The metrics that actually matter

22:56 A week in the life of a CRO at scale

28:32 Navigating compensation at a GTM organization

31:45 What technical CEOs get wrong about GTM

36:01 The role of hunger in great sales leaders

40:35 What makes an exceptional IC sales rep

46:41 Dysfunctional vs. high-performing executive teams

48:01 Chris' most impactful decisions at Snowflake

49:53 "When there's doubt, there's no doubt"

54:49 Learning from world-class leaders

Stevie Case is the CRO of Vanta, the trust management platform serving everyone from founders to Fortune 100 CISOs. A former pro-video gamer who stumbled into sales through a mentor's bet, Stevie has built one of the most unconventional paths to the C-suite in tech. In this episode, she unpacks why early revenue hires fail, what separates a true CRO from a VP of Sales, and why she believes fewer than 10% of current CROs will thrive by 2028.

In today's episode, we discuss:

• Why early revenue hires fail
• What a top 1% CRO actually does
• The scaling mistake Stevie made by copying Twilio's playbook at Vanta
• Why Vanta remains 100% sales-led at every segment
• AI vs. humans in go-to-market

References:

• Cursor: https://cursor.sh/
• Gong: https://www.gong.io/
• Salesforce: https://www.salesforce.com/
• Twilio: https://www.twilio.com/
• Vanta: https://www.vanta.com/

Where to find Stevie:

• LinkedIn: https://www.linkedin.com/in/steviecase/

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 Why early revenue hires fail

02:23 Who to hire at $5M in revenue

04:16 Coin-operated sellers vs. long-term builders

05:57 What excellence looks like in the CRO role

07:44 Metrics, confidence, and velocity

12:04 Should CROs lead sales?

14:39 From shy seller to revenue leader

16:36 Learning to scale at Twilio

17:44 "There is no CRO playbook"

19:58 Stevie's scaling mistake at Vanta

22:16 Why Vanta stays 100% sales-led

23:16 The value of planning 24-26 months ahead

29:54 When trusting intuition was the wrong call

30:49 Do humans still have a place in the future of GTM?

33:33 Stevie's leadership non-negotiables

36:36 The myth of hiring for industry expertise

40:00 What stays centralized in a 600-person company

47:09 The hidden leverage of a customer's first 30 days

53:42 Why the CRO role will face enormous changes by 2028

58:42 What leaders must do now to stay relevant

01:02:30 Unpacking the CEO-CRO dynamic

In the second Executive Function episode, Brett sits down with Ryan Lucas, VP of Design at Rippling. Before Rippling, Ryan led design at Retool and co-founded multiple startups, bringing a rare founder's perspective to design leadership. A trained industrial designer, Ryan traces the roots of modern software design back 2,000 years to make the case that products must be useful, usable, and desirable - and above all, used.

In today's episode, we discuss:

• Why design leaders who stop designing stop leading
• The four pillars every design manager must master
• How to delegate when you're a perfectionist
• Why leaders need strong opinions
• How to scale good judgment
• What Rippling's operating system teaches about speed and commitments

References:

• Airbnb: https://www.airbnb.com/
• Amazon: https://www.amazon.com/
• Apple: https://www.apple.com/
• Asana: https://www.asana.com/
• Brian Chesky: https://www.linkedin.com/in/brianchesky/
• CrossFit: https://www.crossfit.com/
• Figma: https://www.figma.com/
• Honeywell: https://www.honeywell.com/
• Liz Sanders: https://www.linkedin.com/in/sandersliz/
• Nest: https://store.google.com/category/google_nest
• Notion: https://www.notion.so/
• Parker Conrad: https://www.linkedin.com/in/parkerconrad/
• Patrick Collison: https://www.linkedin.com/in/patrickcollison/
• Retool: https://retool.com/
• Rippling: https://www.rippling.com/
• Stripe: https://www.stripe.com/

Where to find Ryan:

• LinkedIn: https://www.linkedin.com/in/ryanwlucas/

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 Intro

00:08 What design actually does at a software company

01:40 The roots of design: from industrial design to software

03:29 Useful, usable, desirable — and used

04:49 How design relates to engineering, product, and marketing

08:15 Measuring success as a design leader

12:40 The gap between director and VP-level design leadership

14:23 Why great design leaders jump up and down in altitude

19:26 The four pillars every design manager must master

21:34 Over-indexing on quality and the perfectionist trap

25:11 When lowering the quality bar actually cost the business

27:53 How to build judgment through pattern matching

31:25 How Ryan's design team differs from the rest

34:31 Why Figma is not the source of truth

36:32 How Ryan spends his week: recruiting, crits, and staff meetings

38:39 The "Do/Try/Consider" framework

42:12 The most important decisions of the past year

44:05 Should one-on-ones exist?

46:45 How to scale judgment

50:49 What to look for when hiring your first design leader

54:54 Advice for young designers who want to lead

58:24 Demanding yet supportive: A balanced management style

01:02:43 What Rippling's operating system teaches about execution

In the first Executive Function episode, Brett sits down with Jeanne De Witt Grosser, Chief Operating Officer at Vercel. Before Vercel, Jeanne spent nearly a decade at Stripe, where she built and scaled global revenue teams and led product partnerships. In this conversation, she unpacks what separates good executives from extraordinary ones, shares her rigorous executive hiring process, and reveals the brutally honest performance review feedback she'll never forget.

In today's episode, we discuss:

• What it takes to operate at 30,000 feet and ground level simultaneously
• The leap from frontline manager to manager of managers
• Inside Jeanne's executive interview process
• The inherent value of driver trees for metrics
• Why context is everything

References:

• Akamai: https://www.akamai.com
• Claire Johnson: https://www.linkedin.com/in/claire-hughes-johnson-7058/
• Culture Amp: https://www.cultureamp.com
• Guillermo Rauch: https://www.linkedin.com/in/rauchg
• John Collison: https://www.linkedin.com/in/johnbcollison/
• Next.js: https://nextjs.org
• Nike: https://www.nike.com
• OpenAI: https://www.openai.com
• Patrick Collison: https://www.linkedin.com/in/patrickcollison
• Stanford Graduate School of Business: https://www.gsb.stanford.edu
• Stripe: https://www.stripe.com
• Vercel: https://www.vercel.com

Where to find Jeanne:

• LinkedIn: https://www.linkedin.com/in/jeannedewitt

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:

(01:17) What separates good executives from extraordinary ones

(02:48) How leadership changes as companies scale

(04:15) What an executive is actually accountable for

(06:11) The leap most rising leaders never make

(07:52) When to dive deep vs. when to step back

(10:09) Teaching people to think like you do

(11:56) Creating a shared language across the business

(13:52) What a COO job description actually looks like

(17:20) The upside of owning the full customer experience

(19:10) Why marketing rolls up under a COO

(21:06) Being demanding and supportive at the same time

(22:33) Inside the executive interview process

(27:35) The workshop prompts that reveal everything

(30:11) The common thread in failed executive hires

(36:36) Metrics: the driver tree philosophy

(43:04 What a collaborative exec team looks like

(57:08) How Stripe got 30 people to operate as one team

(1:03:50) Working yourself out of a job

(1:10:32) The review feedback you can't unhear