Humble, Customer-Obsessed and Relentless: Inside DoorDash's Culture

Yandell opens with a story about interviewing Ryan Sokol, now DoorDash's VP of engineering. He thought Sokol came across as aloof and curt, and told founder Tony Xu he looked like a jerk, which clashes with the company's "no politics, no jerks" culture. Tony asked him to have dinner with the candidate before deciding.

At dinner Yandell asked him point-blank about it. Sokol was embarrassed, wanted to know what he had said, and explained the background to his reactions. Within minutes Yandell's view changed, and the two became good friends. Six months later Sokol said the willingness to blackball a highly qualified person over culture was one reason he joined.

Yandell's takeaway is that when you like a candidate except for one culture concern, giving direct feedback after the interview is a good way to see how they engage and how they take criticism. Someone who really was a jerk would probably not take it well.

Asked about the cheap champagne story, Yandell says it dates to the Series D, a tough fundraise that left the company with little runway. During a press-release meeting, someone fetched inexpensive champagne and plastic flutes, and Tony took the task over from a colleague he thought could add more value. He and co-founders Andy Fang and Stanley Tang stayed up all night assembling around 500 flutes.

The other pillar is customer obsession, which shows up in the WeDash program. Employees must do deliveries at least four times a year, and Yandell does it about once a month, often with his daughters. On one trip, a coffee and sandwich were routed on an 18-and-a-half-mile drive, and his eight-year-old called Tony to say the system was broken.

Tony picked up on the first ring and praised the feedback as some of the most insightful he had recently received. By the time they got home he had emailed the product organization about the problem and a possible fix, and the team was already working on it. Yandell notes Tony does customer support every day, so this was not a one-off.

WeDash also surfaces real bugs, such as routing that used a straight line instead of roads, and employees who cannot deliver can do customer support instead. Yandell says it also acts as a governor on hiring: the company is vocal in interviews that it is expected, which filters for humility and customer obsession.

Yandell has led legal, HR, support, marketing and now BD and corporate development, though not sales. He says he had huge imposter syndrome the first time Tony asked him to run something outside his expertise. Tony gave him David Epstein's *Range*, and explained that an expert is likely to repeat how things have always been done, making a 10x outcome less likely.

His method was to hire the best subject-matter experts and tell them upfront that he knows their field far less well, and say how he intends to help before getting out of the way. He hired Kofi as head of brand, who is now CMO, and the head of legal who became general counsel. Both, he says, are better at those jobs than he was.

He now runs a 12-person org after once leading 1,500 people. People talk about hiring better than yourself, he says, but not about what to do next, which is to slowly get out of the way. That ego-free mindset, he adds, grew out of DoorDash's early days in fourth place after Uber launched food delivery.

Culture is hard to scale when headcount doubles or triples every year, Yandell says, and Tony taught him that written work scales well. His document covers his expectations and the traits he has seen in successful people, how he can improve, and his commitments to the team. He is open that, as a litigator, he tends to argue for sport, which confused his team when he argued against something and then executed it.

The document helped recruit Kofi Amoo-Gottfried, a marketing legend, who wanted to know what working for him was like. He later said Yandell's transparency about his growth areas, and his knowing what he did not know, signalled he would have autonomy. People he has never met have told him they read the doc to acclimate to the fast pace.

Yandell's document promises he will help his reports find their next job, even outside DoorDash. He worried about blowback, but concluded it is better for the company. People are more transparent if they are unhappy or looking, which lets him prepare a backfill and avoid surprises.

He also notes that blind references on managers are increasingly common, and he wants those calls to say that he puts people first. On a five- to ten-year horizon, he argues, that reputation pays back many times over, even if he loses a talented person who would probably have left anyway. DoorDash also sees many people leave and later come back.

He builds it into the routine by reserving the last ten minutes of one-on-ones for career development. When recruiters pinged him about general counsel roles, he forwarded them to Tia Sherringham, then head of legal, so she could learn what other companies wanted. She stayed and became DoorDash's general counsel, and he thinks his loyalty encouraged hers.

Lenny describes Yandell as a unifying force in the C-suite and board. Yandell says it comes down to empathy: understanding how each person is goaled and making them feel heard. In a trade-off between a profitable business line and a nascent one that needed growth, he asked the profitability side for the three best reasons to prioritize growth, and sometimes people persuaded themselves.

Next, he says, be clear about the tiebreaker, who might be the CEO, a GM, or the head of product or engineering, and set a timeline. Yandell says his credibility to call the question comes from having run many functions and visibly not building an empire. Lenny summarizes the approach as steelmanning the other side, naming the decision maker and setting a deadline.

On one-on-ones, Yandell demands constructive feedback and sets aside time for it, pressing if he does not get it. He learned this at Uber, where Travis Kalanick's T3 B3 system required three positives and three constructive points about your manager. Feedback only works if you thank people and then act on it, he adds, reporting back on what changed, as you would for customer feedback.

Yandell relays advice from DoorDash's board that tough times make companies. They reveal who is there for the mission and not a quick payoff, as happened when many people left after Uber launched food delivery. They also force discipline on unit economics, and because DoorDash lacked competitors' funding it had to serve customers efficiently from the start.

Downturns are also good for hiring, he says, since there is more talent available. Surprisingly, internal surveys show people like crises at DoorDash, because there is singularity of focus and the resources follow the main thing. Lenny links this to Frank Slootman's emphasis on urgency.

Yandell says Tony has been talking about urgency since the day he joined and is frustratingly good at it, often moving the goal just when you reach it. He explains Tony's belief in compounding: pushing a roadmap up by even a week, repeatedly, laps competitors who are one week behind. On IPO day, the weekly business review started right after the bell ringing with tough questions and no champagne.

On founders, Yandell says the drive can be lonely and never switches off. The traits he sees in the real ones are obsessiveness, hypercompetitiveness, a knack for manufacturing slights as motivation, and raw curiosity. Tony has built a community of founders at other companies to lean on.

Yandell calls the pandemic a wild rollercoaster while the company was preparing to go public. Volume collapsed in the first days of lockdown, then doubled, just as support centers worldwide shut down and the app crashed most Friday nights. Yet NPS rose, because customers and people earning money through delivery needed the service.

A vivid memory is Tony deciding to cut commissions for restaurants by roughly 100 million dollars. Yandell argued against it, since the company was trying to go public, and Tony told him he was thinking too short-term. He recalls the Ted Lasso line that doing the right thing is never the wrong thing, and says he was never happier to be overruled. Another lesson he took from the period was that everything is temporary, so the highs and lows should not be too extreme.

On fundraising, he says the Series D was very hard, with people doubting the market size or profitability of the model. Afterwards nearly every round was led by an investor who had passed before, because DoorDash only presented numbers it was confident of hitting. He would trade some dilution for that trust, and tells founders it only takes one yes, but you have to keep going.

Yandell jokes that product head Rajat Shroff is effectively head of BD, since the two functions must go hand in glove. The challenge is timing: bring product in too early and you waste scarce engineering talent on deals that will not close, too late and you may have given away bad terms. He now shares pipeline visibility and asks product to flag what matters.

Rajat also taught him to build platforms. Instead of asking for a bespoke build for each DashPass partner like Chase, they create a scalable solution so BD knows the parameters it can negotiate and later partnerships take little effort. Another core value, "dream big, start small," came from an expensive failure with a hotel chain that tried to replace room service, which failed because the franchisees did not care.

The lesson was to test with hacky operations, or just stand out front with a promo code, before spending product resources. Lenny notes that doing things that don't scale still applies at DoorDash's size. On legal, Yandell says Tony and Travis Kalanick both asked questions until they understood the law nearly as well as the lawyers, then applied first-principles product thinking and pushed against overly conservative advice.