Why I stayed at Uber

Deciding to fight for a better Uber, and a better future

Robert Cowherd
Mission.org
17 min readApr 4, 2018

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Disclaimers:
1) These opinions are my own, and not Uber’s.
2) This article is long. For a quick take on my optimism for Uber’s future impact, skip to the “5 Reasons Uber matters for the future” section.

2017 was an incredibly tough year at Uber.

Enduring negative press cycles on a weekly basis and learning shocking revelations about the way some of our leaders had behaved in the past forced many of us to consider whether we had made a mistake by joining. Was I working for an organization whose principles fundamentally differed from my own?

Compounding my internal struggle was a deep skepticism from some of my friends about my continued employment for a company plagued by so much controversy. I saw myself as a builder working to improve urban mobility, and an ally fighting to change the culture of tech in Silicon Valley. But some in my social circles wondered: If I didn’t tacitly support the behavior they’d read about in the news, why hadn’t I resigned in protest?

Last year was one of soul-searching for many of us, and I ultimately decided to stay and fight. I chose to devote my passion and energy to guiding the transition of a brash, revolutionary idea into a trusted civic service that changes the way we live in our cities for the better.

I, and many of my colleagues, are staying and fighting to make Uber the service the world deserves, both for our customers and our employees.

Trusting in your own vision for creating the change you want to see in the world is tough when the vehicle for that vision is under siege for a year, but I’m more optimistic than I ever have been about the impact we can have in the world and within our own organization.

Before I get into why I think Uber is so important for the future, I want to provide a bit of context about how I got here and ultimately arrived at the decision to stay…

My Journey at Uber

Photo by Ian Schneider on Unsplash

Until Uber, my career had been in music & entertainment technology. Having founded a startup for independent artists to book gigs online, followed by 5 years pioneering live video streaming online for high-traffic events like the Olympics, I found myself trading in my engineering chips to become a Product Manager. In 2013, I became the Product lead for the streaming team for Amazon Music’s new Prime Music service (their Spotify competitor).

Amazon was the perfect value exchange for me. In me, Amazon got a niche skill set of deep technical streaming technology knowledge, and in them, I received a 2-year crash course in making smart product and business decisions at a massive scale. It was a great way to leverage my skills as a product founder to learn how to be a PM at a giant tech company. Among the 4 pillars of what makes a fulfilling career, Amazon nailed 3 of them:

  1. Passion: I loved what I did
  2. Skill: I was good at it
  3. Reward: I made good money at it
  4. Impact: Meh? I was certainly making some people happy with the service I was building, but was that enough?

In early 2015, Uber came knocking: “We’re building an Entertainment division at Uber, and we’d like you to lead it.” They had me at hello. Uber’s mission in the world was so compelling, and I saw in it a platform that could achieve a goal I’d always dreamed of since my early days supporting independent artists: the ability to connect people in real-time based on the context of their destination. I personally envisioned a locally-oriented entertainment service that used the preferences of riders to learn how to connect them to the local music happening in their cities all around them that they’d otherwise miss. Finally, the 4th pillar of real impact materialized for me — Uber represented my ikigai:

I joined, and things moved fast. Some highlights:

  • Hired up our music product team in ~3 months
  • Shipped our Pandora integration to give drivers free music without ads
  • Founded a new Hiring Growth team to help Uber grow from ~2,000 to ~15,000 employees in 2 years by getting creative with technology.
  • Shipped Code on the Road to find diverse candidates in places no one else was looking by leveraging our mobile app.
  • Built the #Uberbot with CodeFights to pioneer the “End of the Interview” (bypassing resume screening in favor of proven skills)
  • Led Uber’s Bar Raiser program to ensure we hired the absolute best candidates in Tech and that we dialed out as much bias from our interviews as possible
  • Hired 2 rockstar PMs, Jill and Holly, to scale our programs while I took on Product leadership of our larger Business Partnerships org

I should say it again. Things moved really fast at Uber — faster than anywhere else I’d worked. Our teams were intentionally set up to be autonomous units, with high authority to make decisions at the edge. Things ran lean and fast like a much smaller startup, and we eschewed a culture of seeking permission. It felt like I got more done in a year at Uber than I had in the last 5 years of my career. Coordination and collaboration across teams was tricky, but we trusted each other, and made it work.

I did a lot of recruiting and hiring for my teams back then. This de-coupled autonomy and lack of the bureaucracy typical of other big companies was my strongest selling point to candidates. It worked so well — what could go wrong?

It all goes wrong

I walked into the office on February 20, 2017, and it felt like a bomb had gone off. The previous day, almost everyone in Silicon Valley had read Susan Fowler’s account of the appalling behavior she had experienced at Uber, and the failure of our company to deal with what happened in a just manner.

I rushed over to Holly and Jill, and asked them, “Has this happened to you!!!!??” They assured me it hadn’t, and that this didn’t seem like the company we knew.

But it was our company. And the limitations of unchecked autonomy at the edge became glaringly apparent.

My colleague Aimee Lucido’s incisive response to Susan’s post that day pointed out that pervasive sexism in technology extended far beyond the walls of our company, and that this event should serve as a wake up call for everyone. A year later, it’s heartening to see the awareness that Susan’s story brought to the world and its role in amplifying the #metoo movement. Personally, I’ve had to re-examine a lot of my privilege and naive assumptions, and have redoubled my efforts to come to work every day actively viewing everything we do through the lens of inclusion.

The pain kept coming throughout the year at an unforgiving pace. 2017 brought difficult news on a weekly basis, ranging from misunderstandings like #deleteUber to outright terrible behavior by former leaders. Here’s a recap if you missed it.

People started to leave.

Those of us who stayed realized that we were engaged in a fight for our company’s soul.

When to Fight and when to Quit

How do you know when it’s time to throw in the towel?

As an entrepreneur leading a struggling startup, a Product Manager seeking Product/Market fit for a new idea, and even as a romantic partner, I’ve had to face the decision of “is it worth putting in a lot more effort to make this work, or should I quit now?”

Seth Godin’s “The Dip” addresses this kind of decision making. The thesis is:

  • There comes a time when what you’re doing gets hard and stops being fun.
  • If it is something you can be the best at, stick with it through the “dip.”
  • If it isn’t something you can excel at, quit. And excel at something else.

“The Dip” also references a concept called Zipf’s Law that deals with probability distributions. The idea is that the thing you crush the hardest (the best product, the best relationship, etc.) will be at least 2X better than the second best one you might find, and orders of magnitude better than the third, fourth, or fifth best. Said differently:

The thing you’re the best at will be far better than everything else.

See more examples of the case for being #1 here.

Rank versus frequency for the first 10 million words in 30 Wikipedias. The most frequent word will occur about 2x as often as the second most frequent word, 3x as often as the third most frequent word, etc. Credit: Wikipedia

Fighting for Uber

“It is better to stand and fight. If you run, you’ll only die tired.”
~A Viking saying

What would happen if I ran from Uber? I’d certainly be able to find some impactful way to use my skills in the Bay Area. But where would I go? Considering Zipf’s Law, what was my #1 opportunity to make a difference in the world?

This is Aria, my 5 year old daughter. 😍 😍 😍

Aria in Oakland, CA

When she graduates high school in 13 years, what will the Bay Area look like?

My heart and mind convinced me that no other opportunity or idea in tech is positioned to have the same kind of impact in the world than Uber is right now. Uber’s next chapter matters a lot — both for Silicon Valley’s culture and for the future of how cities work. It matters for the world Aria will inherit.

I chose to stay at Uber to create the change I want to see in her world.

Changing the world requires a world-class organization

Below, I list the top 5 reasons I believe my impact will be greater at Uber than anywhere else. But I can’t believe that any of them will become a reality unless I also believe strongly that Uber is radically improving itself as a company.

The massive change we want to manifest in the world can’t happen unless the world trusts Uber deeply. The only way we’ll build this trust is to work in an ethical manner over a long period of time, and to reward highly principled people for their positive behavior. As Reed Hastings pointed out in the famous Netflix culture deck:

“The actual company values, as opposed to the nice-sounding values, are shown by who gets rewarded, promoted, or let go.”

Here’s what almost nobody outside Uber realizes…

It’s near impossible to believe unless you’re on the inside here, seeing it happen before your eyes. But a real cultural transformation is happening here, and like everything else at Uber, it’s progressing incredibly fast.

When Dara Khosrowshahi arrived as Uber’s new CEO, he issued a new cultural value for Uber: We do the right thing. Period.

It sounded great, but initially I was quite skeptical — I’d heard this kind of statement from business leaders in the past who fell far short of its lofty ambition.

Dara’s actions in the past few months have shown me how serious he is about this mantra, but there was one moment that crystallized my belief. At a weekly All-Hands meeting, Dara fielded “Ask Me Anything” questions from employees. One employee asked,

“Uber’s reputation is in a bad place, and it doesn’t seem like we’re doing much marketing to correct it. What is the plan to improve our marketing?”

Dara’s short response (which I’m paraphrasing from memory) inspired me:

“We don’t fix this with marketing. We fix this by living our principles and doing the right thing for 3 years straight. Focus on making Uber the company it should be, and the world will see it.”

5 Reasons Uber matters for the future

I firmly believe we’re building the right corporate machine to tackle the massive challenges in front of us. With that as a foundation, here’s why I feel so much optimism for the impact I can have at Uber in my career:

1) Leadership on Diversity & Inclusion

Uber can learn from our past mistakes to lead the way in creating inclusive environments in tech.

Some might say that 2017 was a disaster for Uber. I think 2017 was a blessing in disguise. It took a series of disasters to shake Uber from its inertia and force it to change. The deep self-examination and cultural reset that has happened give Uber a unique opportunity to build an entirely new machine — one that can become the standard bearer for how to foster an inclusive culture in the tech world.

Early signs of our commitment to change are promising, but there is a long way to go.

The sexism and lack of concern for creating a safe environment for women that Susan Fowler exposed is not just an Uber problem — it’s a Silicon Valley (and beyond) problem. There is a good chance that Uber’s alumni will become another iteration of the PayPal mafia, going on to carry our experiences forward to found the next wave of companies across Silicon Valley. If we can imprint these leaders with a deep understanding of how to foster more inclusive environments, it could be one of the most powerful ways to move the needle on this problem for the future in the wider Tech world.

For my part, privilege surely played a role in getting me to where I am in life, and in getting me a job at Uber. As Uber’s Chief Brand Officer Bozoma Saint John pointed out at SXSW, it’s up to people like me to acknowledge that privilege, and to use it to reach out and help others up who don’t enjoy the same advantages I do.

The responsibility to work to fix the system is on all of us, and for those who want to make a massive contribution, there’s so much left to do.

2) Sustainability: Reducing wasted resources by reducing ownership

I envision Uber becoming one of the most powerful forces for reducing waste and overconsumption of our planet’s resources in the next 5 years.

Yes. Uber: It may seem strange, but a massive dynamic marketplace at a global scale will be one of the strongest forces for reducing consumption.

We don’t need all these cars. / Image Credit

You’ve probably heard that if everyone on the planet lived like an American, we’d need 4.1 Earths to sustain all of us.

So where does Uber come in?

A car is one of the most wasteful and environmentally damaging things you can own. Buying or leasing a new car every few years means having to manufacture a vehicle, but more importantly, automobiles are massively under-utilized resources. If you commute for 2 hours a day, your expensive vehicle sits unused, wasting space in a city for 22 hours a day.

Sharing this resource with your neighbors means using what we already have rather than having to build more.

Ridesharing still represents only ~1% of the vehicle miles traveled (in the U.S.), with personal car ownership at ~80%. We have a lot of work left to do to make this more sustainable future a reality.

3) Reducing Congestion and CO2 Emissions

I believe Uber can make a step function reduction in congestion and carbon emissions.

Los Angeles is the most congested city on Earth. Here’s a ranking of some of the others. Angelenos spent an average of 102 hours last year in traffic jams during peak congestion hours, costing drivers $2,828 each and the city $19.2 billion.

LA Traffic / Image Credit

Uber isn’t the Sierra club* — we’re a for-profit commercial enterprise. But it just so happens that Uber’s business benefits when mobility in cities operates more efficiently and emits less carbon.

Why?

We want transportation to be cheap, plentiful, and available to as many people as possible in order to maximize the usage of Uber. Congestion limits demand for transportation by making it slower, more expensive, and less convenient.

Uber is proactively backing congestion taxes like this one in NYC and local governments in major cities are following suit, financing mass transit by taxing car usage. Uber is on board with this because heavier use of mass transit increases Uber ridership for the last mile, and because ridesharing works better and sees higher usage with fewer single rider personal cars clogging the roads.

Private car ownership is the enemy

Ubers and Lyfts (in the U.S.) represent only ~1% of vehicle miles driven. The ~80% that are personal vehicles, often with single riders commuting, are the main source of congestion. At Uber, we want to replace the need for personal car ownership with more efficient solutions that work better for cities:

  • Shared rides
    Sharing your ride with 1 or 2 other people means that far fewer vehicles are moving the same number of people, and it lowers your cost of travel. (It can also speed you along in a carpool lane). The idea behind the recently launched Express POOL product is to get hyper efficient with routing and timing, even adding in some walking by riders, so that the entire system can work at high efficiency with lots of seats filled.
  • Last Mile Partnership with mass transit
    Uber complements mass transit well. Trains and buses are great at moving millions of people along fixed routes, and Uber is great at solving the “last mile”, getting you from transit hubs to your destination. If that last mile ride has 3 passengers, great! And if you can avoid a car entirely by snagging a dockless electric bike via the Uber app, even better!
Electric Bikes through the Uber app / Image credit

Uber drives fuel efficiency

Uber drivers are incentivized to drive the most fuel efficient vehicles possible to maximize earnings, and these vehicles emit the least carbon. Once electric grids support widespread adoption of electric vehicles and the economics of EVs are cheaper than combustion engines, EVs will deploy across ridesharing networks far faster than among owned vehicles in the general public.

The combination of more people in fewer cars, and those fewer cars being the greenest on the road, will be one of the most powerful forces for reducing tailpipe emissions in the next 10 years.

*Also, the Sierra club is awesome and you should give them money. :)

4) Economic Opportunity: Fighting Transportation Inequality

I see Uber ameliorating transportation inequality.

Image credit

Uber’s mission of democratizing transportation has the potential to upend the growing problem of transportation inequality in our cities. The sad truth is that many economically disadvantaged people in our cities lack access to quality jobs, schooling, healthcare, and even healthy food because it is simply too expensive or inconvenient to access them from the “transit deserts” in which they live.

Lack of transportation directly impedes upward economic mobility:

I believe that growing the transportation pie so that everyone can get where they want to go cheaply and easily is a social virtue, and the efficiency we’re creating in transport systems is key to making that a reality.

Just how under-served are some of these transit deserts? Take a look at the outer boroughs of NYC pre-and post-ridesharing as an example:

Image credit: Todd Schneider

Ridesharing clearly filled an unmet need, but there are still far too many people who can’t afford ridesharing for daily use.

Boosting low-cost, higher capacity ridesharing options that connect to transit is a key next step to further expanding access in these underserved communities.

Another glaring area for improvement is in healthcare, where 3.6 million Americans miss medical appointments due to lack of access to transportation. That’s 3.6 million opportunities to prevent a condition from becoming more serious and costing far more to treat once it has. Recently, we launched Uber Health to try to address this problem.

5) Future of Cities

Uber can help make cities people-centric rather than car-centric.

Modern cities are broken. They’re designed for the last century’s modes of transportation, and fail to leverage data to make themselves work better. Some cities were designed for cars, instead of for people: 14% of the land area in Los Angeles is devoted solely to parking cars. This is what downtown Houston looks like:

A sea of parking / Image credit

The long term vision of efficiently optimized cars with most seats filled, that don’t require parking at every destination might bring us dense urban cores with 90% of their parking spaces (including on the sides of streets) reclaimed for urban farms, low cost housing, or green spaces!

Image credit

On the way to that goal, Uber is already helping cities re-think how they are organized by sharing our massive data sets with urban planners. With Uber Movement, we have partnered with the city of Cincinnati to help planners visualize how accessible their city is to healthy food options for their residents.

As we’re expanding the data we make available to cities, we’re also making some of our fundamental primitives available via Uber’s API to create a platform for developers to build the next wave of killer apps to make cities better.

What I’m doing now

So, how am I contributing to making this all a reality?

For the past 9 months, I’ve worked in Product Strategy. At a high level, this means that I spend a lot of time focusing on making the decision-making machinery of Uber work better.

Specifically, I spend a lot of time:

  • Doing long term strategic planning to guide decisions around what products to build and where to spend our resources
  • Designing our next generation interviewing and hiring approaches
  • Finding the right balance between speed / autonomy of product teams, and just enough process to ensure we’re making smart and ethical decisions

P.S. We’re hiring…

If what we’re building and what we’re fighting for in the world sounds inspiring to you, let me know…@bobcowherd

Thanks for listening 👏

If you enjoyed this article, feel free to clap a few times 👏 👏 👏 👏 👏 or share with a friend.

Bob Cowherd is a Product / Strategy leader at Uber. Connect with me on LinkedIn or say hi on Twitter.

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Robert Cowherd
Mission.org

Founder @FableSonoma, using neuroscience to foster healing and growth | Ex Product @ Uber & Amazon | Music tech founder | Pilot | Dad to 3 w/ @esthercrawford