One year in on the best hardest job I've ever had

posted by Jeff | Sunday, May 26, 2019, 10:08 AM | comments: 0

In my previous job, I was straddling the line again between hard core manager and software developer, and again I realized how hard that was. Following the "involuntary separation" of that gig, I felt like I had to make a choice about being deliberate to the next level. Someone from the investment firm that bought my current employer found me somehow, and encouraged me to apply, and eventually the rest became history.

I'm a year in now, and when I look at everything that I've done (because one takes inventory when writing a self-evaluation), I'm surprised at the volume of the work. I'm also a little frustrated with the number of mistakes, but I have to give myself a little grace there because this is the largest scope of people and process that I've been responsible for. In fact, that's the real challenge: I know what the right thing looks like, and I've been able to successfully apply it to smaller teams. Now I have to figure out how that works with what will be at least 35 people in my reporting line before the end of the year. That's almost three times my previous record of 12!

Hiring takes an extraordinary amount of time, and because the market favors the workforce, I find that I have to prioritize it even though it's dynamic in its demands. You can't control when people apply or can interview, but you can't move slowly because you might lose the unicorn that you're looking for. I'll close on six hires soon, plus the screening for my product peer, and I've looked at more than 500 resumes this year. While it feels like frenzied work, it's one of my favorite aspects of the job. I've got a pretty good track record of team building, able to see the gaps and match the skills and personalities to fill them. This is one area that isn't that different at this scale, though I suspect it would get harder toward the org size of 50 or 60.

The rest of the job got easier when I realized six months in that I couldn't realistically get in the weeds on everything the way I was used to. I had to delegate and hold accountable my direct reports, and it was like someone flipped a switch when I finally embraced that. I guess I always knew that's what scale required, but I stubbornly thought otherwise. Not only was that change in behavior more effective, but it also gave me a lot more time to look at the bigger strategic problems and give them time. Now I've got a blueprint about where the risks and opportunities are, and can spend time thinking about the tactics to move forward.

And that's why this is so exciting... because just the next year alone is full of really cool stuff that you can only do in a growing company at this stage. It's challenging, for sure, but in all of the right ways. I'm surrounded by excellent people, with a proven business model and a whole lot of potential. The technical challenges are becoming well defined and more of a function of time to solve than difficulty. It checks a lot of boxes, and I'm super excited about it.

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