Last week, I explained my role as a CTO/lead developer on HeatCheck and as a Tech Executive Coach. In addition, I’ve also been working with a startup still in stealth mode, and a property tech company that had almost no technology team before I joined. Each of these companies needs something slightly different from me. For HeatCheck, I’m setting technical direction and implementing solutions in green field space. For the Tech Exec Accelerator, I’m writing training and coaching leaders. For the stealth-mode startup, I’ve been their product lead, and now I’m recruiting (more on that in a moment.) For the property tech company, I’m providing technical direction across an existing (albeit fledgling) business.

It struck me tonight that the sum of these parts was the best part of my last job. Setting product and technical direction, recruiting teams, and coaching individuals. I get to do that with a lot less email, meetings, and commute these days. Of course, none of these projects stays the same very long. They start with product leadership, merge into recruiting, and very soon if all goes well, I’ll be leading a team of engineers and designers to build and launch a new application. Let’s talk about recruiting for a minute.

Stealthy Recruiting

Stealth-mode startups are a funny thing. You’re constantly in this limbo between sharing too little to garner interest and divulging too much that scares people off. This is a startup, after all, and by definition, “startups are bad businesses.” They aren’t suitable for everyone. Even if you are right for a startup, sometimes the timing is off. I had a two-month-old when I joined Bazaarvoice nearly 17 years ago. My wife did not understand. Thankfully, I had good counsel, and that turned out for the better.

Now, I’m the engineering leader, pulling in the initial critical roles to “prime the pump” on this team. We’re trying to fill the key roles of a contract product UX designer and a founding engineer. I’ve had to break my days/work up into smaller compartments to keep track of all of the candidates, interviews, and emails necessary to do this. (I had gotten very spoiled by the support of great Talent Acquisition partners over the last few decades.)

Wall Time vs Company Time

One of the most unexpected observations came when I started working with the property tech startup at a quarter-time rate. They needed technical guidance, but due to budgets (both theirs and also in my capacity), we could only align on a quarter-time contract. That means, each week, I get approximately 8-10 hours of work on their project. So, over the last two months, I’ve logged approximately 8-10 days’ worth of work for them. Meanwhile, they’ve moved the entire company forward by two months. The impedance mismatch between those has led me to do things differently:

1. I didn’t go through as much rigor in the product definition and feature set analysis as I usually would have to validate the needs and designs.
2. I am ruthlessly prioritizing work and using automated tools like ChatGPT liberally to speed up my development, writing, and more.
3. I’m careful to remind myself that I’m quarter-time, and I’m still finishing “week two” on this project, not week nine like my mind wants to believe.

Trying to keep up with the rest of the team and company is a fun challenge. To keep pushing to do the engineering work faster, more efficiently, cheaper, etc., is a skill not practiced in a long time in software engineering (for the most part), but that’s a topic for another day.

Fun