In Depth

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