A journey from engineer to management and back again

At the beginning of 2022 I chose to laterally transition back into an engineer after 6 years in engineering management. There are not many examples of folks making this transition, so I want to share my journey.

Early-career engineer

I joined Yelp as the first engineer on a team to build tools for Yelp's couple-hundred-person sales team. As the sales team grew to a couple-thousand, our team began to grow as well. I was enjoying my role as a technical lead and was building out our initial Salesforce Data Pipeline integration. This was one of our team's biggest initiatives and my first big project in Python. It was also my first time deeply collaborating with another senior engineer at Yelp. I felt like I had hit a good stride.

In my next career conversation with my manager they asked me what I had in mind for myself, say 5 years down the road. I had some prior leadership experience in college and was the team technical lead, and enjoyed both of those roles. So I told them I thought I'd probably want to go into management at some point in the next 5 years, though I didn't know what that would look like. Not long after, I learned something important about management: Timing can be unpredictable as opportunities come and go while you do your best to capitalize on them.

A few months after my conversation with my manager, they approached me and asked if I'd like to explore managing our team in the next quarter. They were going to step up to a higher level and focus on bringing on some new teams and were looking for someone to take their role as manager of our team.

I was initially apprehensive and leaning towards declining the role. I was enjoying being the team technical lead and, while I wanted to explore management at some point, I wasn't sure if this was the time. What if I didn't like it? What if I wasn't good at it? Would returning to a Software Engineer again mean leaving Yelp? Then, as if on queue, a few managers I knew stepped back into Engineer roles. This was the safety net I needed to feel comfortable taking the plunge.

People management

In the years that followed, I enjoyed hiring engineers and helping people on my team grow by mentoring and career coaching. I also managed to stay in the loop on technical conversations and offered as much advice as I could. I knew this was commonly considered an anti-pattern, but given my past history with the team, it was working, at least for a while.

Overall I enjoyed the role, but I also struggled with feeling productive. As an engineer, everything felt concrete. Given a problem, I knew that if I sat down and spent enough time thinking about it and banging my fingers on a keyboard I'd eventually solve it. When I did, I'd get a dopamine rush and feel good about myself. Management was very different. It was often unclear where problems actually lied. Once I identified one, it wasn't always solvable. If I knew how to solve it, I often wouldn't be the one to actually do the solving. I'd instead be guide others to making the right changes.

I described this as trying to steer a bowling ball with a feather. Given enough time and gentle pressure, you'll get the job done, but it can take such a long time that at any given moment you can feel like you're getting nothing done.

When I took on the role of a Director and a manager of managers, my level of influence and ability to coach engineers more broadly grew, but so did my sense of struggle with feeling like I was accomplishing anything concrete. I knew I was probably doing the right thing because my team was successful. The engineers were delivering high quality work and making strides in career growth. During that time, very few engineers left. So I would tell myself, I had to be doing something right... But I couldn't, at any point, tell you what exactly it was.

Starting in late 2019, I started focusing on building teams to support our growing marketing department. Having participated in the implementations of five different Marketing Automation platforms, seen other teams build in house email tools, and having worked with Marketing for years, I felt it important to provide a marketing platform that could more readily meet the needs of our business as well as Keep us nimble as our business evolved.

This was the most clarity I had in my potential impact in my time as a director. I didn't yet have a clear idea how I was going to accomplish this yet, but I had the motivation.

I worked with Marketing to garner support for the broad vision and to better understand gaps and specific capabilities we needed. I also worked with other product and engineering teams to establish mutually agreed upon charters and roadmaps. Throughout, my focus was ensuring that we'd solve the problems at hand, and that we had well structured teams to deliver and support the platform. To deliver on this vision, we had to grow our team significantly. Reviewing candidates and prepping the org for team growth (managers, onboarding) became critical to our future ability to deliver on our promise in a reasonable amount of time. This became nearly my entire focus.

The journey back

By the end of 2021, much of our hiring was complete, we had good agreements on team structures, we had exec buy-in to the plan, and had begun to build some of the early components. It felt to me that I had done everything I could in my current role to advance us towards the goal of building this platform and that “the fun part” was about to begin. I began to feel FOMO from missing out on CEPs, code reviews, and POC building.

When I went into management, I didn't feel like I was "done" with engineering and have kept myself active in writing code by contributing to non-critical Yelp projects and personal projects in my time outside of work. My drive to build things and feeling that my role as an engineer was unfinished never left me. Ultimately, I decided that I could have a greater impact and feel more intrinsic reward by shifting my role back into an IC, in some form.

Where am I now?

When I started my first day as an Engineer again, I didn't have a really clear idea of what my day to day was going to look like. I recognized that there was space for someone take on a role between what I was doing before and that of an engineer, but the details were murky. I wanted to be more involved in building, but still use the skills I developed over the last 6 years to better our team.

I started my transition by reaching out to some of Group Tech Leads on other teams to get a feel for the various ways senior engineers across Yelp contributed to their teams. I also started having more frequent 1:1s with the engineers on my team and began trying to ramp myself back up on our tech stack. Much of the underlying technology is the same as when I left, but a lot of the processes around it had changed. Now, 5 months into the role, I have a much better idea and each day I'm confident that I've made the right choice for me and for my career.

The most enjoyable part has been taking a lot more time to mentor engineers and help our new team Tech Leads take on their new roles. I think that at some point I may like to move back into the manager track, but I'm focusing on the things I love about engineering right now. I'm put people management back on my 5 year plan, but there's no telling how long it will stay there.