I’ve been doing a lot of reflecting recently, and had originally started this post last year after moving to lead the Growth team at Blue Apron. The past year at Blue Apron is definitely worthy of it’s own post at a later date, but thought it would be nice to finish this one as I looked back on how my time at eBay has shaped me into the leader I am today.
My first year was about engineering fundamentals with scale and distributed systems, my second year was transitioning to management, and my third year was about increasing our brand and building partnerships within the company.
Year 1: Professional Software Engineering at Scale
Did I mention that eBay was my first job in the tech industry? It was. I had done some very small freelance projects outside of my main job in the five years between undergrad and eBay, but nothing major. My first year at eBay was all about learning how software gets developed at scale.
The first project I worked on was developing the version of the eBay homepage that users with legacy browsers (IE7 and below). That project taught me the challenges of cross browser support, localization, and accessibility. German text is really long! You shouldn’t repeat a bunch of links on a page, or use the same alt text for links that have different destinations! We were also in the process of launching the then-new eBay Feed to the international community, which gave me a glimpse as to the challenges of internationalizing an e-commerce site with dynamic, user generated inventory (particularly when dealing with a 20 year old code base).
Our next project was building out a new version of the homepage to feature custom, curated content and adding new social features into the feed. We added the ability to follow collections and users and have results from those show in your feed. I encountered one of the more challenging technical problems in figuring out a good way to blend these different updates together (see Blending Lists of Lists for some background).
This project was also a major launch across a number of teams at eBay, with a heavy marketing push and partnerships with celebrities and influencers. It was a great experience seeing how these large projects get launched in a company like eBay.
The next six months were learning about, and iterating on a product. With the newly launched feed, we started gathering user feedback, doing A/B testing, and incrementally changing the product. We went through three visual overhauls. We reduced clutter and changed the item display to show only pertinent information, added a new event type to show up in your feed, and implemented a number of other smaller changes.
Year 2: Transition From IC to Manager
About a year after I started, the team lead left and I was given the opportunity to start managing. I was pretty excited, as this lined up well with my long term goals. Beyond the typical challenges of moving from an individual contributor to managing a team, two other team members on my team left the company in the following months. There was also a reorganization that moved our team from reporting to the NYC office lead to a newly formed Shopping Experience organization led out of San Jose.
I struggled to maintain the product roadmap now that half the team had left. I had previously been a major contributor on the team, and still felt a need to keep that contribution level high on top of my new management duties. This was my first big lesson as a manager: I’d have to trade in some of my productivity as a developer and learn how to delegate better.
I slowly improved as time went on, and it helped especially when we had some new hires join later that year. On the engineering front, I led initiatives to help improve the loading speed of our pages, improve the quality of our code, and efforts to help increase our availability. We shipped further product refinements to the homepage, launching a small refresh in coordination with a brand campaign the company was doing.
I could see the effect of proper management in the numbers. The load times of the page decreased about 10% and the page weight about 40% after optimizing the images that we show and enabling WEBP. The number of production incidents resulting in a call to our team went from about one a month in 2014, to two in all of 2015. The unit test coverage of our projects went from almost nothing to 60% of lines by the end of the year. These were all pretty great wins, but I was stressed out for most of the year.
On the leadership front, it was eye opening being involved as a manager at a large company like eBay. Never before had I been at a central point of many facets of a modern tech company: product, engineering, business, marketing. The homepage for any major company is highly sought after real estate, and being responsible for what 60M people see every day brought with it a whole new level of politics.
Further, the reorganization pushed me from having a pretty hands-off local manager to a focused remote manager. We lost some of our shielding from the affairs affecting the rest of the company, and now I was responsible for that. Making the case for more hires, working on promotion packets, doing performance reviews — all new things I was learning on the spot. Fortunately, past leadership experiences from the Air Force and leading groups during college provided me with a point of reference for viewing myself as a team lead.
During this time I prided myself on getting three new hires successfully onboarded to the team, hosting the first offsite Hack Week at a cabin in upstate NY (the idea for which spread to several other teams at eBay), and maintained high morale despite several large product initiatives and team members leaving. I also started to define the brand of our team throughout the company, as I was now meeting with a number of people in various roles and pushing to have my team’s work recognized by the larger organization.
Year 3: Partnerships, Politics, and Project Management
Coming into my third year, I was felt like I had the basics of leading my team down and was now working on leveling myself up as a manager. What could we be doing better? How could I make my team more agile? How could I get my team members better recognized?
In combination with this, a large new company wide effort began. The company was reorganized again, this time with a focus on aligning teams that were working on the same product area on different platforms. Prior to this, we just owned the desktop web version of the eBay homepage — a separate team developed the mobile web experience, and a third team did the same for the native apps. After this change, our team was now responsible for the engineering for the homepage regardless of platform. My role now became one of building partnerships and coordinating with the other teams while ensuring I could meet the expectations for me to own the broader initiative.
While this change was announced, it didn’t affect the reporting lines for each of these teams. We were coordinating and working on the same product experience, but still reported to three different departments. There was a bigger discussion with leadership about how to address this long term, with unfortunate timing as one of the teams was getting underway on a major project with an expectation that my team would be contributing to it. While more senior leadership discussed the long term solution, I reached out directly with their team to develop a collaboration model that worked for everyone so we could get started.
This first partnership experience played out well, and became a valuable experience. We soon had to do the similar thing with another team. This collaboration was a bit easier not just because I had done it once before, but also because the leadership by this time was much more aligned. As these partnerships were finalized, managing the projects became my next focus. My team was now roughly split into three projects: two separate groups collaborating with different teams in San Jose, and then a couple folks working on the remaining commitments on our original roadmap.
Cross-geography teams can be difficult, but at least we had the advantage of (mostly working) videoconferencing software. I was now project leading two teams of 8–10 people each, and a third team of 1–2. I was fortunate enough to have a solid technical lead on each of the bigger teams, which allowed me to focus on the high level direction of the project and freed up some of my bandwidth to stay in details on the last. This was a great lesson in delegation, and was the first time since year two where I was doing largely managerial work and almost no coding (you can see it in my 2014+2015 review).
During 2015, I again lost three more team members for various reasons. The lessons of before helped somewhat, but the bigger benefit was that we had formed a very tight-knit team, so we were happy that people were moving on to better things. One of my team members got promoted, which was awesome! I also got a new manager as the previous one left the company, and there was one more reorganization that gave us a new director. Both of these gave me the experience of bringing new leadership up to speed on what was happening, and gave me a different examples for what leadership can look like.
These two major projects eventually concluded, with one team being moved adjacent to mine organizationally, and the other being disbanded after the project we worked on never launched. As 2016 began, we had brought in new people in the positions that had been open, and we started work on new project. One of my main goals was to have this project be something the entire team could work on (rather than being split like the year before), which was successful. At the time I left, we also ended up partnering with another team (again using the working model I had created the year before) for a portion of it.
In my final year at eBay, I also started focusing more on developing my team and creating a culture focused on learning and empowerment. These are some of the things that lead to psychological safety. I worked closely with our recruiting team to push to increase diversity in our hiring pipeline, as well as increasing the engineering brand awareness of eBay in NYC.
eBay was an incredible experience to have as my entry into the tech industry. I was fortunate to move into leadership when I did, and a benefit of being at a big company was there were a number of resources to help me grow and develop. I was fortunate to work with some incredibly talented people who I could learn from, and made some great friends.
I’m always happy to chat about differences between life as developer vs. life as manager. If you’ve got questions, reach out to me on my twitter!