We’ve talked a ton about How to Hire a Great VP of Sales on SaaStr, but I wanted to highlight a few VP of Sales “personas” that I rarely, if ever, see work out. Because again and again, many of you will hire this VP of Sales. So many of you will. Especially — when things are going well.
Here are the types of VP of Sales that just never work out. And to be clear — though I said “never”, there are exceptions. Sort of. But make sure that if you do make an exception, you’re very aware of why.
Persona #1: Has Done Another Job Besides Be a VP of Sales for > 1 Year. Now let me be clear — this is very different from someone that’s stepped out of the workforce for a bit to take care of family, etc. That can work for sure. There are many gems there; go hunt those candidates. No, I’m talking about something different. Someone that was a good or decent VP of Sales, often at a well-known startup or company, that just … didn’t want to do it anymore. They’d had enough. So they went off and became an influencer, or a surfboard maker, or a small business owner, or whatever. Sales is hard. VP of Sales is even harder. It makes sense to not always do it forever.
But I see these ex-VPs of Sales sometimes get lured back by the glamor of a hot startup, and actively hunt them. Founders get attracted to their strong LinkedIn … and ignore the fact they quit sales for too long. You might love their background, their LinkedIn, their knowledge base. It’s just that it’s so, so hard to get back in the sales game, especially at a VP level. I’ve literally never seen a single one of these candidates work out at VP of Sales. And rarely below that.
Persona #2: Fails Up Well. For the most part, only those of you that are well-funded will make this error, but many of you that are well-funded will. There are VPs of Sales and CMOs that are great at failing up. Generally, VCs that don’t know sales (or marketing) love them. They are smooth talkers. And they often were lucky enough to be part of a big exit before they had to scale themselves for real. Really do extra due diligence on anyone with a perfect resume at too many hot startups that didn’t stay that long, or were only there in the “lucky” years. They don’t really know how to do it, and in many cases, even want to do it. Often, they just want the glamor of the role. Be careful also with retained search recruiters that typically only work with startups much later-stage than you. They get you a lot of these types of candidates.
Persona #3: The VP That Only Worked in a Small Division of a Big Tech Company. No, working in an “internal startup” at a 10,000 person tech company is not the same. They just lack the skills. You don’t need to hire a VP of Sales that has worked at your exact stage before, but it sure helps if they’ve at least worked at the stage you’ll be at in about 12 months. You will grow into that stage soon enough. Don’t cut corners here.
Persona #4: Never Sold At Your Deal Size. Not Really. This is an old SaaStr theme we’ve talked about again and again. And yet, I see so many of you still not heed it ;). You have to hire a VP of Sales (and VP of Marketing) with experience at your core price point. The playbook is just too different at $3k ACV, $30k ACV, and $300k ACVs. They won’t know the playbook if they haven’t lived it. And you are hiring a VP of Sales in large part for their playbook. More on that here.
Persona #5: The VP of Sales That Can’t Bring Anyone WIth Them. Don’t make this exception. So many founders do. But if they don’t have at least a few great sales execs to bring with them … well, that’s a 100% clear sign that VP of Sales candidate is just a stretch too far. They’re a double stretch. Don’t do that unless you are truly super early stage. Don’t settle for “I’ll hire recruiters” as an answer. More on that here.
Use this checklist when you find a VP of Sales candidate you really like — to challenge yourself. To not be blinded by bling. Want to make an exception anyway? That’s your right. But at least be intellectually honest. Sit down with your cofounder, your seed investor, someone you trust. And talk about if hiring one of these personas really makes sense.
A bit more here: