Tech Leadership across the Startup Lifecycle 👑
Interview with Andrew Twyman — we talk about development rigor, tradeoffs, technical debt, and engineering coaching.
Hey! We are back with another interview with an accomplished tech leader, after the last one with Thiago.
This is a new experimental format that combines video + a regular article. The article includes a summary of what we discussed during the interview, plus my own thoughts about the very same topics.
This time I chatted with Andrew Twyman, Engineering Coach and former Staff Engineer at Dropbox, on a live event in the Refactoring community.
Andrew has had an impressive career so far:
He came out of MIT in ‘99, and joined Maker Communications, which fabricated network processor chips, in the middle of the dot-com boom. He wrote firmware in Assembly and worked through an IPO, acquisition, and subsequent spin off.
Later, he joined Liquid Machines, where he worked on docs and email encryption. The team grew rapidly from 20 to 75 people before crashing in 2008, together with the rest of the economy. Andrew witnessed 3 rounds of layoffs and the final acquisition by a larger incumbent.
In 2012 he joined Dropbox in full hyper-growth phase: the team grew from 250 engineers to 2000+ in about three years, more than doubling year over year.
Today, Andrew is semi-retired—in his own words—and helps tech leaders as a professional Engineering Coach.
What is the most impressive about Andrew’s journey is that he has literally seen it all: from small startups to big tech, together with IPOs, acquisitions, and layoffs.
For this reason, today we will cover some evergreen tech leadership topics for which the answer is usually “it depends” — because Andrew is one of the few who can answer what comes next: “depends on what?”.
Here is what we will cover:
⚖️ Balancing velocity with quality — we talk about abstractions, payoffs, MVPs, and engineering culture.
🦠 Handling tech debt — how to prevent it and pay it down, at various scales.
🪴 Engineering Coaching — why it is still underrated, what it is useful for, and to whom.
Let’s dive in!