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How Brandon Developed a Niche Domain Expertise to Propel His Tech Career

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Brandon Cherry

Product Manager at Upwork

Transition Summary 
  • HVAC/Construction/Roofing/Electrical

  • Global Analytics Engineer @ Under Armour 

  • Implementation Specialist @ Search Discovery

  • Marketing Operations Manager @ Uber

  • Technical Product Manager @ Upwork 

How’s you get started in tech?

When I first graduated high school, I had no interest in going to college. I wasn't a very good student. 

So I actually did four years of HVAC work. I did some roofing and some construction work for a year and then some electrical and after maybe about five or six years school became appealing to me. I got to a point where I was like, I don't really want to do this till I'm 60, but I really don't know what else to do.

So I decided to go back to college which was a struggle. I was older than most of the college kids. And I basically had to start in remedial math and then work my way back through. And then worked my way all through that because I originally went back to school for computer science. But like a lot of computer science majors, I flunked out once I got to a certain point.

Because my program had a no retake policy, I did what everybody does when they flunk out of computer science – I switched to information systems. So I graduated with an information systems degree.

Believe it or not, my first job after that was actually working for Under Armour as an IT help desk intern. And when the IT help desk contract was coming to an end, I just went around badgering people that I wanted to do something a little more in tune with what I'm going to school for. And then I managed to land an interview and get a job offer from Under Armour. 

I spent the next three and a half doing tag management work. At the time, I didn't know why they chose me. I was definitely underqualified. Tag management work was interesting because engineering didn't want to do it, product [teams] didn't really care about it, but it really actually was an important, high touch function. 

I knew enough code in JavaScript compared to my peers. I could write tricky hacks to get things done when engineering resources were lacking. So my career from then on has really been in the marketing tech and tag management systems, which is basically how performance marketing and your pixels optimize your marketing spend.

I also made the career pivot to product because engineering wasn’t for me. I could read enough code to understand it, but I couldn't write it for the life of me.

After Under Armour, what was next? 

I worked with somebody from Under Armor who went to Uber and they recommended that I join and referred me. But it was weird because right as that happened Uber basically stopped hiring. So I applied and then they're like, hey we're actually going to shut down for six months.

So I ended up leaving Under Armor and actually went to a company called Search Discovery. 

But I only spent three months there.  So I got a full remote job, working, which was cool, but a remote was driving me crazy. 

Somebody from Uber reached out after 4 months and was like, “hey, we're interested. Would you want to come in and interview?”

I thought, sure. It's not going to hurt to go and interview. Fast forward, I did an interview and I ended up getting the job, which I didn't expect and ended up leaving Search Discovery after three months, which I felt a little bad for. I just told them if I don't do this now, I'm probably never going to leave the East Coast where I was living at the time. Uber gave me the opportunity to relocate and move to California. So I moved to San Francisco sight unseen. I had been there once.

I booked my apartment online in the first six months. I was living in Bayview of San Francisco for a while, which was a fun experience taking the train line into work.

The web team at Uber was super duper small. And I was on a lean functional ops team. So I would say I've been more of an ops person for a long time. I don't necessarily consider myself a product person. I got the title cause that's what I negotiated, but I'd say it's more of an ops specific role.

I started working in tag management but that ended up getting into a lot of other things at Uber, such as doing GDPR CCPA compliance. And when I was at Uber, that's where I actually planned to switch into a PM route through privacy and compliance.

That was like my only route into the PM world. But as I was making that, they were just taking a little too long to make the transition. In the process of that I did the engineering interview there and bombed horribly in front of my peers. So that was like, it was probably one of the more painful things I did.

So then I had somebody from Upwork reach out and then I applied and during that application process, it wasn't initially for a product role, but I negotiated my way into a product role.

What drove you to Uber and then to Upwork? 

Remote work and money were important. I was able to really bump up my income and negotiate that pretty quickly. At Under Armour I started as an intern, I was probably being a little underpaid for my skills so I was able to negotiate with Search Discovery at the time.

And then when I went to Uber in three months. So in a few months I was able to make 2 pretty big salary leaps. 

Also retail (Under Armour) is very slow growth. When Uber came along and it was just like, this is a no brainer. Everybody knows who they are.

I joined Uber in 2017 right before a really rough, long IPO. I got there when everybody had to become adults. We had to grow up, get serious, and do all the pre IPO to IPO stuff and really buckle down.

I was there for four and a half years. It was just taking a little too long to get the role I wanted at Uber. And Upwork came along and it was a full remote job. So it was like a remote during kind of COVID time. And I wanted to move out of the city.

My first bosses and mentors, they're like, you're either gonna become one of two things. Super generalist, which I feel like most product people are usually more generalists. Or highly specialized in what you do. I became highly specialized. 

This tag management thing has been a very lucrative, specialized career. It changes slightly from place to place, but the overall concepts still remain the same between tag management systems and CDP systems. But yeah, it's been like a very niche field that I've been in for quite a long time. 

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How did you negotiate from the original role that Upwork was offering you to the product role that you wanted?

I just said, “Hey, basically, I'm looking for a product role.” I know that I'm pretty sure it was a marketing ops role. And they tried to actually switch me back. But I just put my foot down. I was like, I didn't come here to do that. 

A lot of ops people do product stuff. I just basically said, Hey, I want a product role. If you can get that, I'm all on board for joining you guys. And I think I just had skills that they needed at the time. So they agreed to it.

What were some of the challenges that you faced along the way as you were navigating into this product path? 

I would say it's been incredibly difficult because I went to school when I was older. It was frustrating for a long time, not getting to where I wanted to be, but just staying the course is going to be your best course of action if this is what you really want and you really want to do, you will figure out a way to get to that point. 

It's never easy. I started my career later. I definitely felt a little behind at the time. I would say now I feel like I've caught up to career leveling but when I first started, I felt like these 20 year olds were way ahead of me. But they really weren't, it's just all in perspective.

Second I would say when I made an effort at the engineering thing, I totally bailed, totally just crashed and burned. And I think that was embarrassing. And I think you really learn from those embarrassing moments. 

Then the big challenge getting into product was convincing people that I deserved to be over there. At Uber, to show them I was able to do everything a product person does, I created a new API, created an endpoint, I worked with engineering, I allocated resourcing. Just kept throwing myself out there. 

Like I said, I was told I was going to be highly specialized from the get go. I just didn't think about it, but then, fast forward 10 years, they were exactly right. I just feel like as long as you keep trying and you put yourself out there and you really make a valid effort, things work out.

How’d you overcome those challenges?

I'd say I've been incredibly lucky to have really good bosses and really good good mentorship and advice throughout. But I'm also a big fan of just taking chances. 

I have a bunch of skills, but ultimately this expertise around performance marketing and tag management was the one that really paid off for me in the end.

I read a billion API docs in my own time and just read the documentation. My job isn't that hard to be quite honest, but people just don't want to do the reading. Just do the reading. If you read everything that Google or wherever, whatever tool you're working on produced, I guarantee you'll become an expert. If you just read, tinker with it, try it out, get a sandbox, play around. 

Transition Tales