In Depth

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