The product wisdom every CPO should ignore | Jeremy Epling (CPO, Vanta)

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Mar 19, 2026

Jeremy Epling, Chief Product Officer at Vanta and former product leader at Microsoft and GitHub, reflects on moving from big tech to startup life. He discusses staying close to product details, keeping shipping velocity as teams scale, owning final decisions at the C‑level, and running open office hours to demystify leadership.

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INSIGHT

Owning Engineering Enables Faster Tradeoffs

Combining product, design, and engineering under one leader speeds decision-making across trade-offs.
Jeremy argues a single throat-to-choke enables quick calls on re-architecture versus feature trade-offs.

ADVICE

Mind Meld With Your Product Founder CEO

Align with the CEO on product vision, guardrails, and the CEO's preferred level of involvement.
Jeremy maps Christina's passions and assigns PMs so founders can run initiatives without derailing EPD work.

ADVICE

Pair Founders With A PM When They Lead Features

If a CEO wants to own a product detail, pair them with a senior PM and designer to translate vision into execution.
Jeremy always assigns a PM so the CEO isn't pulled into day-to-day minutiae.

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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