During David Singleton’s tenure as Chief Technology Officer at Stripe, the company’s approach to evaluating prospective engineers diverged sharply from the traditional industry norms. Instead of relying on standard, formulaic tests or requiring candidates to work out solutions with dry-erase markers on whiteboards, Stripe pursued a more thoughtful, authentic strategy. Interview questions were carefully composed by employees who not only understood the company’s technical challenges but could also anticipate the skills that would best predict long-term success. This meant that for applicants hoping to secure an engineering role at Stripe, the evaluation process resembled the actual day-to-day environment of writing production-ready code, rather than an artificial, high-pressure exercise in memorization. The interview room, in other words, had no need for whiteboard markers — the laptop replaced the board.
For many software engineers aspiring to break into prestigious technology firms, platforms such as LeetCode have become a sort of rite of passage. These online resources provide a vast repository of coding problems and algorithmic challenges, serving both as a training ground and a filtering mechanism during the hiring stages. Companies frequently turn to these kinds of standardized assessments as a first layer of triage: by requiring applicants to solve practical but generic questions, hiring managers can quickly eliminate weaker candidates while also conserving resources. Furthermore, using such widely available question banks helps curb the problem of interview content being leaked and recycled across candidate communities. Yet Singleton suggested that this widespread reliance on prepackaged tests often came at the expense of authenticity and failed to capture the true qualities that distinguish an excellent engineer.
At Stripe, the philosophy was different. Singleton explained on an episode of *The Peterman Pod* that he deliberately drew inspiration from the company’s most accomplished engineers when shaping the interview process. Instead of reusing universal problem sets, questions were sourced organically from within the organization. This approach not only ensured originality but also elevated the quality of the assessments, as the contributors themselves were deeply familiar with the nuances of real engineering work. Another key departure from convention was Stripe’s abandonment of whiteboard-based coding exercises. Singleton recalled that when he joined the company in 2018, technical interviews across the industry frequently involved standing at a board to scribble solutions under time pressure — a format he personally experienced in every interview before Stripe. To him, the practice felt both impractical and detached from the realities of professional software development.
Singleton elaborated that the core belief behind Stripe’s revisions was simple: whiteboard interviews do not realistically simulate the environment in which engineers operate. Writing pseudo-code on a wall, without access to standard development tools, is a far cry from solving problems in a modern programming ecosystem. Instead, Stripe designed its interviews to mimic real collaboration. Candidates would work on laptops equipped with editors and tools they already knew, and they would actively pair program with the interviewer. The intent was to observe how engineers think, adapt, and solve problems in a setting that mirrored the workplace rather than an artificial academic exercise. The ultimate objective, Singleton stressed, was to provide applicants with the most authentic and fair experience possible, giving them a genuine preview of the role they were being considered for.
Host Ryan Peterman raised the point that many large organizations remain attached to services like LeetCode, with the justification that standardized platforms lower the risk of question leakage online. Singleton acknowledged this widespread concern and admitted the challenge it created for hiring teams. Once an interview problem appears publicly, its effectiveness as a measurement tool diminishes; candidates who encounter it later may simply memorize a solution instead of demonstrating their problem-solving ability in real time. Therefore, companies must constantly replenish their supply of unique prompts to maintain fairness. This dynamic invariably makes crafting good, fresh questions a difficult, ongoing endeavor, and Singleton conceded that Stripe too faced this challenge. Still, instead of outsourcing the task or reusing clichés, Stripe leaned on its own engineers to voluntarily contribute new ideas. Singleton frequently expressed gratitude to those who participated, even recognizing their efforts during company-wide engineering meetings and noting that such contributions could meaningfully boost an employee’s standing in the organization.
The pragmatic benefits of this methodology were clear to Singleton: though time-intensive and resource-demanding, it allowed Stripe to uphold both originality and integrity in its selection process. He emphasized that creating novel material for interviews was unquestionably laborious, especially at a growing company, but he believed firmly that the investment was worthwhile. Stripe, which recently announced plans to expand its workforce to roughly 10,000 employees by the end of 2025, remains far smaller than titans like Google or Apple, each employing hundreds of thousands globally. This disparity only strengthened Singleton’s view: if a comparatively lean organization like Stripe could commit the necessary effort to design high-quality, customized technical interviews, then companies with vastly larger headcounts and deeper resources had no valid excuse for over-relying on outdated or impersonal methods.
After stepping down from Stripe in October, Singleton began a new chapter by co-founding /dev/agents, where he now serves as chief executive. Reflecting on Stripe’s practices, he argued that while constructing original, internally sourced interview prompts was undoubtedly challenging, the ultimate payoff was significant for both the company and its incoming talent. He pointedly remarked that if enormous technology firms such as Meta or Google claim they cannot allocate the resources required to design improved interview systems, he remains unconvinced. Given their scale, finances, and talent pools, they could absolutely create more meaningful evaluations if they truly prioritized doing so.
In sum, Singleton’s perspective underscores the value of an interview approach anchored in realism, collaboration, and authenticity. Rather than grading candidates on their ability to recall algorithmic trivia in a sterile environment, Stripe actively sought to replicate the contexts in which its engineers thrived. This philosophy not only benefits candidates by reducing unnecessary stress but also yields more reliable assessments for the company itself. It is an approach that challenges the industry to rethink ingrained traditions and to build hiring practices that genuinely reflect the work engineers are expected to perform.
Sourse: https://www.businessinsider.com/former-stripe-cto-technical-interview-strategy-whiteboard-2025-8
