I'm interviewing a lot with early-stage companies, in search of a leadership role above that of line manager, even if temporary. The title bump always matters, much more even than an IC (Individual Contributor) role. Four years as an Engineering Manager (EM) at a well-known and successful company meant it was easy to get another EM job; they hired me directly as my first EM title, but that's far more rare, and in fact I'd spent the 3 years prior struggling to land one. I suspect that companies' reasons for not hiring EMs directly are not usually the right ones, but the end result is the same either way. They get more skittish as you go up the ladder, but now I have a neat confluence of (a) understanding why I enjoyed joining a 55-person company, and (b) having the freedom to join something even smaller.
My friend Alexa, although I'm older and helped her navigate her way into leadership, has been moving in executive circles for quite a while now, and gave me some immaculate advice about interviewing for things like Head/VP of Engineering jobs, and why that might be a better fit for me. When you're talking to a younger company, and especially at the executive level, they want to see who you are, and not just if you're comparable to another employee with the same title. Basically, I show them a Chris-shaped human, and the two sides together talk about whether they have a Chris-shaped space.
My whole life, I have been utterly unable to not be Chris-shaped, except for very short periods. I'm terrible at it. It has caused me a lot of trouble, but on the other hand I have needed to spend less time figuring out who I am. A Chris-shaped job at an earlier-stage company can save me a lot of stress, by not having to convince entrenched people they need a Chris-shaped person. Or, at least, I convince the founders and executives, and then back it up with competence.
(Or get removed, I suppose. Some of these can also turn out to be inherently time-limited, since I can most certainly pull off scaling an Engineering department to somewhere in the 30-60 range, it's rational enough for you and/or your investors to want someone more experienced in the 200+ size.)
I'm finding I learned a lot from this past job, which was not an earlier-stage startup, and it comes out in how I talk about the job, what's important to me, what I think should be important to them. I feel more rooted, and that I'm inhabiting my professional space more fully. No small part of this is that I took care of myself after Tim died, and took a placeholder job that wouldn't push me very hard.
And now I can choose what I want to do.
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