As you scale up in SaaS, one thing I can almost guarantee is that you are going to hire some VPs who were either fired or quit their last role. Especially in the Bay Area. There’s so much change and turn-over in the Bay Area many of your top candidates will have had some bumps in their transitions from their last role.
There are lots of reasons for this:
- All your hires can’t either be (x) folks you magically poach from other companies and (y) folks who magically are leaving another great gig at the perfect time to join you.
- And more importantly, change happens at start-ups as they scale. VPs that do a great job at $1m in ARR rarely are the perfect leader at $100m ARR. So many of the very best VP candidates are folks who turn over in high growth start-ups.
- Passionate stretch candidates do quit when they are “topped”. I.e., when a boss is brought in above them. And sometimes, those folks can be the perfect candidates for your stage and company.
- And finally, VPs make mistakes. They join start-ups out of passion and belief. But often, they don’t really have all the data and metrics, or even really know what they are getting themselves into. Sometimes they join impossible situations.
So you’ll end up hiring VPs who went through a significant transition at their last gig, sometimes an involuntary one. That can be great. Just a few thoughts of things to look for:
- Be wary of candidates that bad mouth their last CEO. It can be tough to hold your tongue. But I’ve generally found that candidates who bash their prior boss in an interview tend to do it again at their next gig. Even best case, they tend to be less loyal and less reliable. The best VPs really do hold their tongue here. They are good managers, and they know there is no upside here.
- Be wary of candidates that take no accountability for what happened. If the last role didn’t work out, the best VPs are honest about why. They share their mistakes and learnings. The ones that don’t, often lack the self-awareness and maturity to succeed in the next gig.
- Be wary of VPs that don’t have anyone to bring with them. If a transition happened for the “right” reasons, often, some of her team will want to come with her on the next journey. If a VP candidate has no one she can point to that will join her from the last role, that’s a flag.
- Be wary of VPs that did odd things after a traditional role. I know some folks will challenge this, but if a VP went off and did something very different — be way. Exploring new roles and ideas is great. But if they were a CEO for a long time, or took a very different functional role (e.g., in customer success when they were in sales) … usually their heart really isn’t into it. Not always. But usually in my experiences. Definitely give these folks a shot. Just double check they really want it for the right reasons.
- Be wary of too big a chip of the shoulder. We all have a chip on our shoulders. It’s what drives us in part to be great founders and startup executives. But too big of a chip can blind you to what it really takes to go big the next time. It’s hard to quantify this, but you can feel it. When the candidate has too much scar tissue, too much of an edge. Again, some chip on the shoulder is good. But a huge one tends to create teamwork and aligment issues in your VPs.
- One exception to the 2 year rule is fine. More than one — just be cautious. A candidate that stayed 2 years at her last gig and then transitioned out? There usually are few issues there. Someone that left after 6-12 months — and more than once? Do more homework to really understand why. So much changes in start-ups. If a candidate had success for 2+ years, that’s often equivalent to infinity. That’s usally enough in my book. But shorter gigs are still a flag, even in the high velocity world of 2018+. This may not be fair, but I’ve still found it to be pretty true. Especially at the VP level. You really don’t get the full benefit of a VP until year 2 anyway, once she’s not just figured it out, but build and honed her team.
Finally, if you just aren’t sure … have your most trusted outside advisor interview the VP candidate. Her insights may not be 100% accurate. But usually it’s a great way to get a quick read if you have any concerns on these 5 potential flags.
You’re still going to hire VPs with some of these flags. Just go into it being clear about the issues, and where you’re going to need to backfill and help her/him succeed.
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