Phil Freo, VP of Product and Engineering at Close, has lived the rare arc from founding engineer to executive leader. In this conversation, he breaks down why he stayed nearly 12 years, and what it takes to build a team that people actually want to grow with.

We get into retention that is earned, not hoped for, the culture choices that compound over time, and the practical systems that make remote work and knowledge sharing hold up at scale.

Key takeaways

• Staying for a decade is not about loyalty, it is about the job evolving and your scope evolving with it

• Strong retention is often a downstream effect of clear values, internal growth opportunities, and leaders who trust people to level up

• Remote can work long term when you design for it, hire for communication, and invest in real relationship building

• Documentation is not optional in remote, and short lived chat history can force healthier knowledge capture

• Bootstrapped, customer funded growth can create stability and control that makes teams feel safer during chaotic markets

Timestamped highlights

00:02:13 The founders, the pivots, and why Phil joined before Close was even Close

00:06:17 Why he stayed so long, the role keeps changing, and the work gets more interesting as the team grows

00:10:54 “Build a house you want to live in”, how valuing tenure shapes culture, code quality, and decision making

00:14:14 Remote as a retention advantage, moving life forward without leaving the company behind

00:20:23 Over documenting on purpose, plus the Slack retention window that forces real knowledge capture

00:22:48 Bootstrapped versus VC backed, why steady growth can be a competitive advantage when markets tighten

00:28:18 The career accelerant most people underuse, initiative, and championing ideas before you are asked

One line worth stealing

“Inertia is really powerful. One person championing an idea can really make a difference.”

Practical ideas you can apply

• If you want growth where you are, do not wait for permission, propose the problem, the plan, and the first step

• If you lead a team, create parallel growth paths, management is not the only promotion ladder

• If you are remote, hire for writing, decision clarity, and follow through, not just technical depth

• If Slack is your company memory, it is not memory, move durable knowledge into docs, issues, and specs

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