I was recently chatting with a friend who asked about finding senior leadership roles, and particularly doing so while you’re already gainfully employed. The context of this discussion was managerial leadership roles within a software engineering organization, which for convenience I’m defining as leading groups of 20+ engineers (e.g. Director at Series C or later company) or being a functional leader of a smaller team (CTO, VPE).
Conducting a career search within these roles is odd for a few reasons:
There are many unfilled roles (folks in these roles get near-constant outreach)
Nonetheless, it’s relatively hard to discover the roles because they’re often unposted and being sourced by an external recruiting firm
Even when you do find an unfilled role, it remains unfilled for a specific but unobvious reason (usually some combination of interviewer misalignment, outsized expectations, inconsistent compensation, difficult environment to succeed in, etc)
With those factors in mind, how I’ve seen folks find senior engineering manager roles is:
Peer-driven discovery – the general belief is that the best roles are neither posted online nor sourced by executive recruiting firms. Instead you have to know the folks involved. More commonly, you need to know folks who know them and can throw your name in the hat
Applying directly, kind of – there are some publicly posted roles, which are helpful for discovering roles. I’d generally recommend finding a backdoor entry into the search though, either through an executive you know at the target company or (much easier) having a friendly recruiter who knows a recruiter at the target company introduce you
Executive search firms – these vary tremendously, and importantly it’s not just that firms vary, it’s that the individual recruiters vary a great deal as well. These do primarily focus on functional leadership roles (CTO, VP Engineering, etc), but some will work on the next tier of roles like VP Infrastructure Engineering and so on. Ask friends to refer you to specific recruiters they’ve worked with before
Crowd-sourced searches – I run a small, informal, and private mailing list where we co-share inbound executive searches. Especially when you’re not looking, it’s interesting to see a crowdsourced cross-section of opportunities that your group is seeing. I imagine other folks have similar groups
Sharing availability online – I’ve seen a decent number of folks find interesting roles by sharing their search on Twitter. This is, of course, not ideal for folks currently in a role
Pulling that all together, if you’re trying to find a role right now, then ask your friends for
introductions to executive recruiters they’ve worked with.
If you’re trying to find a role in six months, make sure your trusted network is aware that you’re looking.
If you’re trying to find a role next year, work on being more discoverable, which I’ve written about previously in the tongue-in-cheek titled How to be a tech influencer.