Back in the Engineering Saddle Again

A little over two years ago, fresh off the heels of helping ready my company’s part of the Internet for the GDPR, I offered to again take up the leadership of a small team I had led before – this time to launch another SaaS offering – this time in payments. The opportunity aligned well with my personal goal of leveling up my leadership skills with what was then an eye on a director of engineering role, and it also aligned with a engineering roadmap I had set forth nearly five years ago to get hardware related work (specifically integrating our software with mobile payments and point of sale hardware) into the company.

My team launched the next step of that vision earlier this year, as WooCommerce Payments, on time and (mostly) on scope. Looking back, I’d say I enjoyed the earliest parts of the project the most – when the team was smaller and the emphasis was on nailing down the architecture and tech stack. In hindsight that’s a key observation. Of the things I had on my plate – people management, project management and technical leadership – I found myself increasingly spending the majority of my time in people and project management and less and less in architecture and the tech itself.

I’m quite grateful to Stripe for setting an expectation at the beginning of the project that (eventual) hardware integration was a requirement – because that has opened a door for me to pull a phoenix and re-birth myself with a focus on technical leadership. I’m keeping myself laser focused on that this time around. 🙂 And I want to still spend more time with people, but not as their manager. I’d rather be a mentor. I learned that too.

I also owe a debt to an article by Charity at where she so eloquently laid out this engineer-manager-engineer pendulum that so many of us engineering types do 🙂 It helped shine a light on the path forward.

So, there you have it – a brief retrospective of my experience as a team lead / engineering manager. Onward and upwards!

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