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First Round CapitalWhy great leaders make themselves obsolete | Eric Sager (COO, Plaid)
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Episode Details
EPISODE INFO
- Released
- July 16, 2026
- Duration
- 1h 10m
- Channel
- First Round Capital
- Watch on YouTube
- ▶ Open ↗
EPISODE DESCRIPTION
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-
4536710
• 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
SPEAKERS
Brett Berson
hostHost/interviewer at First Round Capital focused on leadership and org design.
Eric Sager
guestCOO of Plaid, speaking about leadership, org design, and scaling through major company events.
EPISODE SUMMARY
In this episode of First Round Capital, featuring Brett Berson and Eric Sager, Why great leaders make themselves obsolete | Eric Sager (COO, Plaid) explores Plaid COO on resilient culture, org design, and leadership obsolescence Eric Sager says leading through repeated external shocks at Plaid is less about reacting to events and more about sustaining an always-on focus on serving customers and the broader ecosystem.
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