Phil Freo

On The Tech Trek: Retention for Engineering Teams

3 min readLeadershipRemoteEngineeringClose

Recorded September 2023

I was recently a guest on The Tech Trek podcast to talk about my journey from founding engineer to VP of Product & Engineering at Close, and what keeps people around for the long haul.

Play

A few of the things we talked about:

Why I joined (and why I stayed)

I joined for the founders and the team, not the idea. When I joined, we weren’t even working on Close yet – we were trying a “salespeople as a service” model and building internal software to make our sales team more efficient. We quickly realized that internal software was the secret sauce, and within about six months we pivoted to productizing it.

People ask why I’ve stayed almost 12 years. My answer: the job keeps changing. First it was learning a new framework and literally building the software. Then it was learning to hire at scale. Then learning to manage a team. It keeps challenging me. On top of that, the quantity and quality of what we’re able to build keeps getting better as the team grows – and the people and values have stayed great.

“Build a house you want to live in”

That’s one of our core company values. Most people aren’t joining for a year or two and leaving, and we’re not trying to build a company to flip it. So let’s build a company, a team, and a codebase we actually want to live in for a while.

Some other things that help with retention:

  • Remote. People who live somewhere only because of a job are harder to retain long-term. Being remote let me move back to Florida to start a family near our parents.
  • A real IC track. You shouldn’t have to go into management to get promoted or make more money.
  • Leadership opportunities for senior engineers, on both the technical and project-leadership side.
  • A mix of internal promotions and seasoned outside leaders, so we’re not stuck with only one viewpoint on how things are done.

Remote work that lasts

We’ve been fully remote for about seven years and are now at 90+ people. A few things make it work:

  • We hire mostly within US and European time zones, so we still get synchronous overlap. We’re not 100% async.
  • We get the whole company together in person once or twice a year, and smaller teams meet up throughout the year. That carries us through the rest of the year.
  • We hire for strong communication skills – especially written.

Documentation, and making Slack expire on purpose

When you’re remote, you have to over-document. Once you’ve answered a question three or four times, it’s time to write it down. We also watch our bus factor: no one person should be the only one who knows how something works.

One interesting thing we do: unlike companies that treat Slack as a permanent knowledge base, we keep a short retention window on Slack messages (we’ve experimented with as little as 30 days). If something matters, it belongs in a doc, wiki, or GitHub issue that’s designed to last and be searchable.

Bootstrapped stability

Close has been bootstrapped and customer-funded for a long time. What the VC world might call “slow growth” has been steady, healthy growth – and it means we’re more in control of our own destiny when the market or funding environment changes. While many companies have frozen hiring or done layoffs, we’ve been able to double down and hire.

Initiative is underrated

My main piece of career advice: people at every level underestimate the impact of their own initiative. Don’t wait for someone to tell you exactly what to do. The more senior you get, the less you’ll get direct answers – you’re expected to come up with the good ideas. One person championing a better way to do something can really make a difference.