Why big‑tech execs often fail at startups

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