Stripe CEO Says His Top Leaders Interview a Customer Twice a Month

Digital payments platform Stripe invites customers to join its management meetings every two weeks to gather “candid feedback,” according to co-founder and CEO.

In an April 8 post on X, Collison revealed that a customer participates in the first 30 minutes of the meeting, which includes about 40 senior leaders from across the company.

“Even though we already have a lot of customer feedback mechanisms, it somehow always spurs new thoughts and investigations,” he wrote.

This initiative underscores Stripe’s ongoing efforts to stay closely aligned with its user base. Founded in 2010, Stripe is considered the most valuable private fintech company globally, with a as of its last funding round.

Growing Pains and Customer Concerns

While Stripe continues to grow rapidly, some long-time users — particularly smaller businesses and indie developers — feel the platform has shifted focus toward large enterprise clients. However, Stripe’s performance metrics suggest otherwise. In a February annual letter, Collison shared that Stripe’s payment volume reached $1.4 trillion in 2024, marking a 38% increase from the previous year.

Additionally, Stripe noted that it now serves half of the Fortune 100 companies, emphasizing its ascent from a startup-friendly platform to a major enterprise payments leader.

In response to a query from Cloudflare’s CTO about participating in one of these meetings, Collison replied, “Would love to have you guys… will reach out.”

Criticism From the Indie Community

Despite the positive response from many quarters, there was criticism from independent developers and smaller businesses. One investor wrote:

“Hi Patrick — you know I admire @Stripe — but you should pay attention to the extent things have degraded for the indie community using Stripe. I messaged support a week ago — no reply, things are super complicated. There’s more stuff, but it’s a mess.”

Others, however, praised the initiative. One user commented that the practice helps “keep the culture focused on what matters.” Even Elon Musk chimed in, simply stating: “Good idea.”

This mix of feedback demonstrates the ongoing challenge for Stripe: balancing its continued growth into the enterprise market while maintaining a strong connection with its grassroots user base.

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