Stripe Engineering with Raylene Yung

Stripe is a payments API that allows merchants to transact online. Since the creation of the payments API, Stripe has expanded into adjacent services such as fraud detection, business management, and billing. These other verticals leverage the existing customer base and infrastructure that Stripe has developed from the success of their payments business.

Raylene Yung is the head of payments at Stripe. She joins the show to talk about her work, which includes elements of engineering, product development, design, and management. All of these dimensions of her job came up in our conversation, which made for a wide ranging conversation.

This interview comes in the context of Stripe’s rapid growth. The organization is changing, and Raylene explored the questions that Stripe is asking itself internally about org structure. Namely: what is the tradeoff between a defined, hierarchical structure of direct reports versus a decentralized, flat org structure? Is there any advantage to making roles highly defined (such as “senior infrastructure software engineer”)? Or is it better to let people have fluid roles, and self-assemble?

Raylene was willing to explore these questions–and I found her answers highly useful and thought provoking.

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