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Back to Uber

It’s also doggo friendly. Bailey’s back, back again.

My experience at Uber

When people asked me what it was like working at Uber, I often shirked. If we were close enough, my honest response was, “Kind of like the stories. More misogyny, less sexual harassment than I thought.” If we weren’t, I’d shrug it off casually and change topics.

The truth is, when I left, I never thought Uber would take the steps necessary to really turn the ship. Some of the most toxic people I’d ever met were the highest performers. There was truly a prevalence of “brilliant jerks”. I remember often going in to meetings asking how long I’ve worked, where the “real” SEO lead was (because where is HE), what level I was or how many people I managed (like it was a measure of competency).

But for the many negative experiences and confrontations I encountered, there are so many unspoken positive experiences I remember and cherish. There are so many women, men, learnings and experiences I was grateful for. Take for example the web lead I indirectly worked with, who was one of the strongest female leaders I have ever known. I always imagined her to be my “psuedo boss” – a dotted line who was my rock at Uber who gave me the feedback and support I needed to push things over the line that felt too herculean to push myself.

And words can’t even express the love and pride I had for my own team, (100% female, just saying) that could throw down SEO with the best of them. Even the people who challenged me, I appreciate that they made me tougher and helped me appreciate my own (at times inflexible) values and sense of conviction.

And I’d be remiss to not highlight the many, many strong incredible working moms and peers I worked with in digital marketing, engineering and product at Uber. The incredible tens of thousands women of Uber who somehow managed to care for their kids, listen to their partners with open ears and hearts after a long day of work, care for the dogs we’d coo over, and still get their work shit handled day after day. Truthfully I’m barely surviving with a (middle of the road) dog. To this day their strength, energy and abundance of love humbles me.

There are so many of these people who were there, and are still there at Uber, and I wish people knew their stories and hearts in the way I feel I do.

Dropbox is one of the most special places I have known

Dropbox is truly one of the most special companies I have ever known. I hope that if I ever start a company, that I could foster the sense of goodness that exists within Dropbox. Dropbox is the kind of place you can go up to a complete stranger and ask for help, and 100% get it no questions or expectations asked. It was the kind of place where if you were new to the company and your manager hadn’t taken you to the weekly Happy Hour, people noticed and sat with you while privately chiding your lead. It’s the kind of place where when people heard about a vendor worker being treated unfairly, they would use the company’s budget and loyalty as leverage to ensure that worker was given the rights or protection they needed. Temp, contract or full-time, you were a part of the Dropbox family and people moved to protect you.

It’s the kind of place where men would never dare to use the word “aggressive” or call female coworkers a “bitch” out loud. Where instead they’d proudly wear women@ shirts challenging others to, “unlock their feminist energy”. It’s a place where women who look like me can succeed.

It’s the kind of place where I see people eat lunch together every day because they really enjoyed it, not a lunch meeting planned weeks in advance to, “align with your stakeholders” (aka peer reviewers).

So why go back?

I’ve long felt like I wasn’t quite done with my Uber journey. When I left Square, I remember talking to our CMO as to why I was leaving. Knowing the reputation, he asked if I was nervous. I admitted I was but referenced Jeff Bezos’ regret minimization framework.

“I knew when I’m 80 I would never regret trying this thing I was super excited about, and it failing….It was a 100 percent chance of a regret if I didn’t try, and basically a zero percent chance of regret if I tried and failed. I think that’s a useful metric for any important life decision.”

I would 100% regret not having taken the Uber job. I 100% still am nagged, each and every day of the things I wish I could have achieved. I am 100% proud that I (hopefully) made the smallest of footprints there, and I ruminate every day about what I could have done differently. I 100% believe that Uber is a company that is not done changing how we live and work. I also 100% believe, that they are trying to do better and have already set the wheels in motion to do so.

“We all get to choose our life stories….It’s our choices that define us, not our gifts. Everyone has many gifts. I have many gifts. You can never be proud of your gifts, because they’re gifts: they were given to you. You might be tall….or extremely beautiful–but you can only be proud really of your choices because those are things where you are active. One of the most important choices that each of us has is you can choose a life of ease and comfort, or you can choose a life of service and adventure. When you’re 80, which one of those things do you think you’ll be more proud of? You’ll be more proud of choosing a life of service and adventure.”

Today, I choose adventure and service. I choose being the change I want to see and be in the world: at Uber, in SEO and tech at large. I choose to aspire to be a leader who believes in leading with the heart, and to let others see that values like trust, dedication, these are infectious. I want to be a part of creating special teams. The kind I hope everyone gets to experience at least once in their lifetime – the teams that simultaneously manage to do the best kind of work together, while giving unfiltered feedback with the best intention, while having an unreasonable amount of fun at work together and providing real business value with people and leaders you love and follow.

That being said, I know I’m in a lucky place to have optionality in a time where 30 million have filed for unemployment. I’m embarrassed to admit that historically I’ve mostly supported animal causes, but before leaving Dropbox I maxed out my annual donation, with the majority going to the SF Food Pantry. Dropbox matches FTE donations up to $2K a year.

  • $125 to Planned Parenthood
  • $1,875 to The Food Pantry SF
I even got engaged in my Uber hoodie. Something I wasn’t #superpumped about LOL. I was hoping for a different outfit and significantly more makeup.

I know it’s not nearly enough, but I’m hoping that $3,750 can help provide some food and resources for families in the Bay Area. If you’re in the position to, please consider donating time, food or money to food banks in your area. Food banks are being hit particularly hard – a friend came to tears when he was dropping off food recently and saw cars lining up for miles during the current times.

Truthfully I am an imperfect person marred by many flaws, contradictions, and shortcomings. Likewise Uber is a checkered and imperfect company. But I believe we both are moving to the same north star, to become the company whose values, contributions, and character reflects the change we want to see in the world.


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