On the COO job with Claire Hughes Johnson (Stripe) x Gretchen Howard (Robinhood)

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Claire Hughes Johnson (former COO at Stripe) and Gretchen Howard (former COO at Robinhood) join The General Podcast for a rare, candid conversation about what it really means to operate at the highest levels inside two of the most ambitious fintech companies of the past decade.

Both left safe jobs to take bets that looked “crazy” from the outside. Both joined hyper-growth startups without the COO title, built trust with founders in real time, and ended up shaping the companies from the inside out. In this episode, they dig into what the COO role actually is, how to avoid “organ rejection” when you’re the outsider, and why the people function is the most underrated lever for scaling.

You’ll hear Claire and Gretchen swap notes on why the hardest problems are often unglamorous—compliance, self-clearing, comp plans—and why the real work is about earning trust, building velocity, and protecting the integrity of the company as it grows.

In this conversation, you’ll learn:

1. Why Claire and Gretchen said yes to Stripe and Robinhood when everyone around them said no

2. Founder chemistry and how to know if you can actually work with someone

3. How to walk into a COO role without blowing up the culture

4. What founders get wrong when hiring their first COO

5. How Stripe and Robinhood scaled the ‘unsexy’ parts of business

6. How to build systems without adding bureaucracy

7. How to use the people function as a strategic weapon

8. Being okay with not being liked as your leadership evolves

9. Claire’s “full stack leader” framework

10. What great operators actually obsess over

Where to find Gretchen:

• LinkedIn

Where to find Claire:

• LinkedIn

• X: @chughesjohnson

• Book: Scaling People