From Jeff Bezos’ grind to Deep Sentinel

David Selinger, former Amazon manager of customer behavior research and later cofounder of Redfin, built a career on large-scale data and volatility—then turned that playbook into an AI security startup, Deep Sentinel, that now stops thousands of active crimes

When David Selinger walked into Amazon in the early 2000s. he didn’t expect the job to change how he saw the world. He said he went in “nonchalantly” after feeling bored in a comfortable tech role at Dutch Bros. where he was running their tech side and working very few hours for a pay day he didn’t need to chase.

At Amazon, the atmosphere was different enough to make time feel like pressure. Selinger. now the 48-year-old CEO of Deep Sentinel. described a gladiatorial culture where he worked 80 hours a week. with an approach that removed what he called the coordination and restrictions other traditional companies relied on. It wasn’t just hard work; it was a belief system. “Jeff Bezos made me rethink the way I view the world,” he said.

Selinger’s path to Amazon ran through Stanford. He went there but didn’t finish his degree, then returned in 2000 to complete it. In 2002, while still in college, he got hired at Amazon through on-campus interviews. He joined what became the customer behavior research group in January 2003. when the group had “a few thousand employees” and was based in an office called Pac Med.

On average, he said he met Jeff Bezos once or twice a week. His office was down the hall from Bezos, and he remembered hearing Bezos “laughing constantly.” Selinger called Bezos “great and amazingly intense,” and he said the proximity made the intensity contagious.

What pulled him in wasn’t only the people—it was the problem. Selinger said the data side of Amazon appealed to him. pointing out that even in that era few companies used the word “terabyte” to talk about data. He described the chance to work closely with Bezos while working on something he wasn’t yet experienced with: large data sets.

He also framed Amazon’s early momentum as a direct challenge to outside pessimism. When he joined. the media assumed Amazon would go out of business “this quarter or next.” Selinger said Bezos “steamrolled ahead” anyway. and Amazon took on debt to build warehouses because Bezos had “confidence and clarity. ” helping the company overcome what others considered impossible.

As he absorbed how Bezos thought. Selinger said he learned a rule that seemed simple only from a distance: common sense requires common assumptions. Bezos. he said. invented the two-pizza teams—small units led by intense. independent squads that “don’t collaborate; they’re sent out to battle.” Many people argued the model would fail and that people would quit if they were organized that way.

Selinger said Bezos responded by challenging the assumption behind the criticism. The first assumption, Bezos told the room, was that leaders want to keep people. Selinger said Bezos treated that belief as negotiable: if the assumption is that leadership wants to keep people. then the team design should reflect it. Bezos also planned leadership rotations out of mid-management every 12 to 24 months in Amazon’s early days. In Selinger’s account. Bezos believed the company could attract the best talent and get the most out of it within those 24 months.

The structure wasn’t built for stability, Selinger said—it was built for volatility. Amazon, he said, reinvented organizational structure “from being for stability to being for volatility,” and found strong talent through that method.

That talent and that volatility would eventually intersect with another big leap: turning data into new business lines. Selinger said that in building his team. Bezos had to convince the board of directors that building a team that would use Amazon data was unique. Selinger described his own biggest accomplishment at Amazon as persuading Bezos to allow the advertising business unit to exist and grow.

Their first meeting, Selinger recalled, included a blunt line from Bezos. Amazon is a retailer, Bezos said—they “don’t put ads on our website.” Selinger then showed data meant to prove the company should run ads. He said Bezos approved the advertising plan after seeing it.

Despite recognition as a high performer, Selinger left. He said he walked away from “so much stock,” and while he didn’t realize how big it would become, he still wanted to start his own thing. He left Amazon in 2004.

His next move was Redfin, which he cofound­ed, and where he served as CTO. He described a quick, focused runway: he worked full-time for a year, got the company funded, hired a CEO, and then moved on.

He then started Rich Relevance, a machine learning enterprise software company for big retailers, which would later merge with another company. He called that period “the hopping stage of my life.”

Eventually, his love for AI shifted from product work to mission. Selinger founded an AI security company called Deep Sentinel. He said the goal was to create a startup with an “unequivocal positive impact on the world.”

Deep Sentinel’s model. as he described it. combines cameras and a back-end service that connects the cameras to an AI. and then connects that AI to live guards. The company, he said, stops thousands of active crimes every month at an affordable price point. Deep Sentinel manufactures its cameras, provides the guard service, and builds its software and back end internally.

Selinger said he self-funded the start and invested about $1M before bringing in outside backing. He described partnership funding with Jeff Bezos, one of Deep Sentinel’s earliest investors. When Selinger reached out, Bezos agreed to be part of it.

Family helped early too. Selinger said his daughters did early branding work and logos, and also discussed how the company would work and operate and what technology it would build. He described himself as both a dad and a CEO who still works a lot.

He manages the company while operating across geographies. Selinger said he has offices in Makati, Philippines; Taiwan; and Pleasanton, California. He also said all his US employees are remote, and that he goes into the office once or twice a month.

In his telling. the through-line is clear: Selinger says his experience at Amazon became the foundation for his career—an education in treating assumptions like engineering inputs. pushing hard problems with data. and building organizations designed not just to grow. but to keep moving when the outside world expects you to stall.

David Selinger Deep Sentinel Amazon Jeff Bezos customer behavior research two-pizza teams Redfin Rich Relevance AI security machine learning Pleasanton Dutch Bros