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When David Singleton was CTO of Stripe, interview questions were hand-crafted — and there were no Expo markers needed.
For candidates looking for engineering jobs, tools like LeetCode have become a right of passage in the hiring process. The platform’s practical questions often are used to weed out first-round applicants, saving time and preventing questions from getting leaked.
At Stripe, Singleton crowd-sourced interview questions from high-achievers at the company. Engineers also didn’t have to write out their code on a whiteboard, he said on “The Peterman Pod.”
When Singleton began at Stripe in 2018, the handwritten technical interview was still popular, and some employers still use this technique. He said that all the interviews he did before Stripe involved a whiteboard and he found these tests impractical.
“We believed and believe today that that’s actually not a great way of simulating what it’s like to see a real engineer do work,” Singleton said. “At Stripe, we designed an interview process where folks would actually be on a laptop with all the tools that they were used to having and pair programmers with an interviewer.”
Singleton’s goal was to give candidates “the most realistic experience of work that we could.”
Host Ryan Peterman told Singleton that large companies used services like LeetCode to reduce the odds candidates would post interview questions online.
“It is the case that interview questions get leaked,” Singleton said. “As soon as that happens, you need a new interview question because you want to make sure that you’re fairly assessing people and getting a real read, not the people who search for it on Google beforehand.”
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That made writing original and unique interview prompts challenging, he said. To source these questions, Stripe looked internally.
“It was a volunteer effort to build those interview questions,” Singleton said. “I would get up at engineering all-hands and say thank you to the folks that have done this. Honestly, it contributed to their advancement in the org.”
Earlier this year, Stripe anticipated it would have 10,000 employees by the end of 2025. That compares to Big Tech giants like Google and Apple, which each employ over 100,000 employees.
Singleton’s new company is even smaller: He left Stripe in October to serve as co-founder and CEO of startup /dev/agents.
At Stripe’s size, Singleton said creating original questions for Stripe was “hard work,” but worthwhile.
“If you tell me that Meta or Google don’t have the resources to build good engineering interviews, I don’t believe you,” he said. “They could totally do this if they wanted to.”
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