In Depth

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:

References:

Where to find Christopher Payne:

Where to find Brett:

Where to find First Round Capital:

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:

References:

Where to find Katie:

Where to find Brett:

Where to find First Round Capital:

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:

References:

Where to find Jay:

Where to find Brett:

Where to find First Round Capital:

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:

References:

Where to find Jeremy:

Where to find Brett:

Where to find First Round Capital:

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:

References:

Where to find Keller:

Where to find Brett:

Where to find First Round Capital:

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:

References:

Where to find Chris:

Where to find Brett:

Where to find First Round Capital:

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:

References:

Where to find Stevie:

Where to find Brett:

Where to find First Round Capital:

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:

References:

Where to find Ryan:

Where to find Brett:

Where to find First Round Capital:

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:

References:

Where to find Jeanne:

Where to find Brett:

Where to find First Round Capital:

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

Anil Varanasi is the co-founder and CEO of Meter, which provides full-stack networking infrastructure as a service for businesses. Since founding Meter with his brother Sunil in 2015, Anil has been playing a distinctly long game in one of the most entrenched markets in technology, betting on vertical integration, business model innovation, and a multi-decade time horizon. In this conversation, he unpacks Meter’s origin story, from four-plus years of heads-down R&D, and shares how his unconventional approach to planning, management, and pace keeps him excited to run the company for decades.

In today’s episode, we discuss:

Where to find Anil:

Where to find Brett:

Where to find First Round Capital:

References:

Timestamps:

(01:27) Meter’s unusual timeframes

(04:06) “We don’t do OKRs”

(06:32) How to plan without planning

(08:31) Track your unhappy customers

(11:43) How Meter’s journey began

(15:02) Dissecting the 2010s SaaS boom

(17:06) The networking industry trap

(21:44) Meter’s first roadblock

(22:07) Why Shenzhen accelerated Meter’s progress

(26:29) The process to get a sales-ready product

(31:02) Why you should own the full stack

(32:45) The surprising thing you should innovate

(35:03) Avoiding the one-trick pony trap

(37:39) The secret to finding an excellent market

(43:48) How COVID’s constraints propelled growth

(48:25) Why founders need to know their customers

(49:34) Why Meter didn’t sell via traditional channels

(51:44) You need “seller-market fit”

(54:51) The danger of meta-work

(56:25) Decoupling management from authority

(1:02:17) When the person is the problem

(1:05:05) The inherent value of going slowly

(1:09:41) Running a company for as long as possible