A Few Types of Senior Hires You’d Think Would Work Out … That Don’t

We’ve talked a ton on SaaStr about how to hire a great VP.  We even have 3 great checklists to make sure you hire right:

• VP of Sales hiring checklist here
• VP of Marketing hiring checklist here
• VP of Customer Success hiring checklist here

Beyond that, there are also a handful of VP personas that CEOs hire again and again … that don’t work out.  A quick list, just to think about before you hire one of them:

• The Amazing Industry Expert.  It can be so tempting to hire that industry luminary as a VP of Success, or VP of Product, or otherwise.  Every startup has room for a great evangelist or two, and maybe make space for that hire.  But the Amazing Industry Expert rarely is truly great at the functional area you hire for them.  And especially — for your stage.
• The One That Used to Do The Job, But Then Did Something Very DIfferent for a Long Time.  This is very different from someone that steps out of the workforce for a bit for family or other similar reasons.  Those can be amazing hires.  No, what I’m talking about here is someone that was say a VP of Sales for 8 years, and then spent 4 years doing something very different.  Running a surf shop.  Or consulting for too long.  Or taking up aquaculture farming.  VP jobs are too intense, and require too many skills.  Once you go off and do something very different for a while, I just rarely see those candidates step back into their old role.  Because if they really wanted to do it, they would have stayed in that role.
• The One That Will Do the Job But Only if It’s Combined With Another One.  The VP of Sales that now wants to be VP of Sales and Marketing.  Or Sales & Customer Success.  Or the VP of Marketing that now also wants to run sales, too.  Ambition is good, but skipping too many steps isn’t.
• The Proven Superstar That Really Just Wants to Consult 40% Time Now.  Consultants can help you for sure in a startup, although too many can break you (too many folks giving advice, not enough folks doing it).  But what doesn’t work that great is when you hire a 40% VP that doesn’t really want to own the core KPIs or dedicate themselves to the role.  It can be OK for a short period.  But I see founders keep these folks in a part-time role way too long.  The effectiveness tends to diminish fairly rapidly.

Just a few personas I see founders hire in a tough recruiting environment that look like a decent bet.  But in the end, usually aren’t.

A related post here:

(note: an updated SaaStr Classic post)

Published on February 11, 2023