Hiring Winning Operators: Lessons from the early days of Uber
When Uber launched in 2009, it wasn’t just a ride-sharing app — it fundamentally altered how we move and live. In the years that followed, it sparked conversations about innovation, the gig economy, and the future of transportation. Regardless of what you opinion on Uber is, it changed the world.
Uber was a great idea but an incredibly difficult one to execute. We're diving into the story of how Uber assembled a team of killer operators who turned ambitious plans into reality and propelled Uber to the heights it has reached today. These operators were the driving force behind Uber's meteoric rise, and their story offers invaluable insights for anyone looking to build a team that can execute big visions.
Hire operators who just make things happen
In the early days of Uber, Travis Kalanick was known for having an unconventional approach to hiring. He didn’t have a ton of faith that the standard interview process was going to get him the best people, similarly to Sam Altman at OpenAI.
The first CEO of Uber, Ryan Graves, caught Kalanick’s eye with a single tweet. Kalanick posted on Twitter that he was looking for a product manager and “biz-dev killer,” and Graves responded with a simple tweet that changed Uber’s trajectory: "Here’s a tip. Email me :)." That tweet led to a meeting, and Graves and Kalanick launched UberCab a few months later.
Obviously, this was bold of Graves — and it’s almost certainly exactly why he got the job. In the tech world, there’s a lot of talk about hiring brilliant engineers, talented salespeople, and visionary leaders. But the backbone of a truly successful business is its operators: the on-the-ground doers and problem solvers who turn ideas into reality.
Ultimately though, at a startup, everyone is either an engineer or an operator. An operator is someone who executes, transforming strategic goals into actionable plans. Someone has to do the dirty work, and hiring people who will is vital to a startup’s success.
Uber went on to hire a team of operators who embodied ruthlessness, resourcefulness, and a relentless drive. They got shit done, but they didn’t just execute tasks — they built the foundation for a global phenomenon.
Ruthless goal pursuit: The Uber Edge
Graves and Kalanick knew that for Uber to succeed, they’d need to hire people who were ruthless in achieving their goals.
Take Austin Geidt, one of Uber’s first employees. Starting as an intern, Austin cold-called drivers, handed out flyers, and took on any task necessary to push Uber forward. She would sometimes take customer calls at 3:00am — but her willingness to take on any task, and her relentless drive to make things happen set the tone for Uber’s culture.
As they launched in new cities, Uber faced significant regulatory hurdles and operational challenges. The team’s ability to navigate these obstacles was what made Uber successful. In San Francisco, the team worked around the clock to sign up drivers using tactics like approaching drivers at cab stands. They often worked late into the night to make sure they had enough drivers on the road to meet growing demand. This kind of dedication is what separates good operators from great ones, and every startup needs people with this level of focus and efficiency in the face of adversity - to do whatever it takes.
As they expanded into larger markets, Uber’s operators had to be both aggressive and strategic, often engaging in negotiations with city officials and adapting the business model to comply with local regulations. This kind of strategic ruthlessness not only helped Uber establish a presence in these competitive markets, but it also set a precedent for how the company approached new challenges.
No work is beneath anyone on the team
In the early days of Uber, roles were fluid and responsibilities shifted rapidly. The best operators showed an incredible ability to pivot and take on new challenges. You’ve heard a million times that you should hire people who can “wear many hats” — but what that actually means is finding people who approach each and every task with the same level of determination and resourcefulness. For Uber’s early team, whether they were managing driver relationships or launching new markets, each task was taken head-on.
But what did this actually entail? It took a lot of humility. Humility meshed with a fierce determination to succeed is a powerful combination. Great operators don’t have an ego when it comes to their work — they are willing to roll up their sleeves and tackle any task, big or small. At Uber, this expectation was what fostered that relentless pursuit of goals. Early Uber employees knew that they had tons of hurdles to overcome, not all of them pleasant — but if they didn’t overcome them, no one else would.
Navigating ambiguity with a “just-figure-it-out” attitude
By the time Uber launched in Washington, D.C., they were no strangers to conquering regulatory hurdles, having been coined as a “feisty startup” by the media. The stakes were high, but luckily, they had hired Rachel Holt as a General Manager to launch Uber in the city. With little guidance, Holt knew she had to just make it happen, and ten days later, Uber had their first ride in D.C.
Hiring people with a “just-figure-it-out” mindset became Uber’s secret weapon. After breaking through regulatory walls in D.C., they were hit with 25 charges in Toronto, “including operation of an unlicensed taxi brokerage and unlicensed limo service. Figuring how to respond regulations and laws — and how to just stay in operation anyway — became part of Uber’s playbook. They needed people for whom shutting down was simply not an option, whatever the cost.
From day one, Uber built a culture that embraced this mindset. Take Austin Geidt, for instance. She joined the company as an intern and, without a clear role, faced endless challenges. She persisted, and over a decade later, she left as the Head of Strategy and Business Development for our ATG unit, right before its acquisition by Aurora. Austin’s story is Uber’s story: failure was never an option. It’s not about having all the answers but having the relentless determination to find them.
And this wasn’t just the case for Uber’s operators. With their user base skyrocketing, the engineering and operations teams needed continuous innovation to keep up. Conrad Whelan, Uber’s first engineer, was a prime example. He tackled everything from building the app’s initial sign-up flows to optimizing dispatch algorithms, eventually building out a full product development team in the Netherlands.
Every person Uber hired early on, whether an operator or engineer, had to thrive in ambiguity, see the big picture, and get things done. It wasn’t just a skill set — it was a survival tactic. It was this relentless drive and adaptability that kept Uber from falling apart and propelled them to the heights they’ve reached today.
Find people who will never fold
Just a few months after Graves and Kalanick launched UberCab, they were issued a cease-and-desist by two regulatory bodies in San Francisco. This was one of many critical points for Uber, where the company was teetering on the brink of failure. They quickly assessed the situation and decided to continue operations, risking a $5,000 fee per instance of operation and potentially 90 days in jail each day that the company remained in operation past the order.
Many would have folded under this amount of pressure, but Uber didn't. The early team didn’t buckle in the face of this challenge — they were motivated by it. They were proactive, devised a strategy, and kept their sights on expansion in the following year. This wasn’t just a tough situation; it was a make-or-break moment that demanded swift, strategic action, and they used it as an opportunity to thrive
The founders knew that very minute at Uber was going to be a battle, and they needed people who could react quickly but with a well-thought-out strategy. The best operators foresee challenges, plan several steps ahead, and pivot swiftly when those plans go awry. Proactivity and organization are not just nice-to-haves; Uber shows us they are essential traits that can make or break a startup.
By setting this bar from the beginning, Uber ingrained these traits in their culture, building the foundation for a relentless crew. They hired people who understood that time was their most valuable resource, and wasting it was not an option.
How to find killer operators for your startup
Hiring operators who will drive your startup forward involves more than just ticking off a list of qualifications. You need to unearth the hidden gems who want to get things done, no matter the odds. Here's how to spot the true operators who will propel your company to success.
1. Focus on hiring the bold — not just the brilliant
Let’s be clear — you definitely want smart people in your corner. But to find those people, there’s too much emphasis on by-the-book academic achievements. You’re building a team of doers, and those people can take all sorts of paths. Geidt, for example, graduated from UC Berkeley at 25, when she was already five years sober after battling a drug addiction. After seeing a tweet that Uber was looking for interns, she cold-emailed Graves to ask for the job, who told her to make a presentation about herself. She hadn’t had any luck in the post-2008 recession job market, so she took a risk — and sent a deck full of pleas for Graves to give her a shot. This was a far stronger signal of Geidt’s audacity and boldness than any academic accolades would have been, and she proved her worth.
Ways to achieve this:
- Use the news for candidate sourcing. The people who have publicity usually have it for a reason. Pay attention to TED Talks, innovation awards, conference speakers, or even high-profile activists. These are the types of people you want on your team — who’s to say you can’t pitch them a job?
- Ask them straight up. Boldness is not something you can really coax out of people, but it’s something that’s easy to sense. When you ask someone to talk about the boldest or riskiest thing they’ve done to succeed or meet a goal, the truly bold will not only have an answer at the ready, but they’ll be bold enough to tell you.
2. Look forward to being challenged
You want to find insatiably curious candidates. Look for those people who challenge you right from the start. Seek out individuals who don’t just accept the status quo but question it. When you’ve found these people, it will emerge in your first conversations with them. Someone who’s willing to take the risk to challenge you shouldn’t be off-putting — it’s a selling point. These are the people who won’t hesitate to debate ideas, push boundaries, and explore uncharted territories. Look for the ones who make you rethink your own assumptions. You want curious minds who will push your company forward.Ways to achieve this:
- Conduct reverse interviews. Dedicate an entire meeting with a candidate where they are meant to interview you. See how much they’re willing to dive in to get the real answers to what it’s like working with you. See what happens if you try to skirt around giving a real response — will they double down, or will they back away from pressing you on it?
- Have a debate. Let the candidate pick any topic, and debate with them on it for 20 minutes. This will get them out of their comfort zone and force them to disagree with you, and you’ll get a good sense of how comfortable they are doing that.
- Make them roast you. Have the candidate tell you what you could be doing better. Talk them through a strategy or a plan, and let them pick it apart, but make them back it up. This only works if you’re really committed to being challenged by your team — and it’s a very quick way to weed out people who have a working and communication style you won’t vibe with.
3. Seek those who seek chaos
Even if you’re not Uber — battling regulatory challenges at every turn and keeping up with crazy demand — startups are chaotic. Pretending otherwise and masking this to candidates is a disservice to your team and your mission. Acknowledge the chaos up front and actively seek out people who are not only undeterred by it, but who are motivated by it. Startup experience is good, but don’t overlook those who have sought out their own hustle: they’ve survived the gig economy, worked in high-stakes freelance roles, or turned passion projects into profitable ventures. A lot of people would consider this work unskilled, but in reality these are the battle-hardened operators who have already hustled their way through chaos.
Ways to achieve this:
- Lead your search with an emphasis on this trait. If you post that you’re looking for an Operations Specialist, you’re going to get a million applications that will tell you very little about a person’s ability to deal with chaos. Activate the networks of your team, your investors, and your colleagues to specifically ask who they know who has truly thrived in hectic environments with little direction.
- Ask them to achieve a goal. Depending on a candidate’s availability, hire them for a 1-2 day project where they’re only told to achieve a goal given a certain scenario, like figuring out how to launch a product in a new market or devise a product feature that will solve a theoretical problem. The idea here is to see how they respond given little information and whether they’re capable of achieving a goal regardless.
Building a legacy of ruthless operators
Uber’s early days taught us one invaluable lesson: the true drivers of success in a startup are the operators; those gritty individuals who turn plans into reality. These are the people who choose to thrive in chaos, relentlessly pursue goals, and tackle every challenge with unwavering determination.
Encourage a culture where these traits are valued and nurtured. Empower your team to take ownership, think creatively, and embrace the unknown. By doing this, you’ll cultivate a legacy of strong operators who can drive your startup forward, adapt to new challenges, and ultimately scale your business to new heights.
In the end, it’s the operators who will turn your startup dreams into a thriving reality. Invest in finding these people, support their growth, and watch as they lead your company to disrupt industries and achieve success. Just as Uber did, your startup can become a force to be reckoned with — driven by a team of exceptional operators.
Start your search today.
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