I get sent this resume to review all the time. Director+ of Sales at Slack / Zoom / Mongo / Datadog / Qualtrics Your Brand Name SaaS Company. Took Hot Start-Up from $0 to $50m as VPS from Day 0. Was there “early” through IPO and did amazing things.

That all sounds impressive, for sure. But were they great? Or just lucky?

The thing is, it’s actually hard to know on the surface. Because it’s not ARR growth or even an IPO alone that determines if a VP of Sales him or herself is great. Because so many people were involved in getting Salesforce to the first $20,000,000,000 in ARR. It’s really how well they did based on a situation.

Now …

• Come into a #2 player and turn it into #1? That’s kind of amazing.
• Come into Salesforce at $2 billion ARR and help it get to $5 billion? I mean, that’s great … but … not the same thing.
• And there were probably 100+ RVPs of Sales at that point. They aren’t all great. Really, only a subset are — at least in the context of jumping into a VP of Sales role at a SaaS start-up.

So when I meet a Candidate from Very Well Known B2B Company, I add a few extra questions to my interview, and focus extra on some we always try to ask.

To see if they really did it … or at some level at least, were just lucky.  Or at least, had so much help, so much infrastructure … that they may not be able to do it at a true start-up in a competitive environment.

My extra questions:

• How much of your team did you actually recruit yourself?  This question is always important, but especially for someone from a Very Successful SaaS company. Because often, the managers were given a team, or a lot of it. That’s not remotely the same as recruiting your own team.
• What’s your current team-level quota?  And what % of quota did you hit last year?  If she manages, say, 8 reps, what’s the total quota she’s responsible for? 8 x $800,000 = $6.4m, for example. You’d be shocked how many “directors” and “VPs” at bigger SaaS companies that are in “sales” don’t have a quota to hit. Pass on these hires. At least until you’re at $100m ARR. Maybe, always.
• Why / why weren’t you promoted?  This is a trick question, in a way. Promotions are important, but a ceiling is less of a flag for me. It’s OK if your Director of Sales from BigSaaS Co never made VP at a BigSaaS Co. There may be many good reasons. Management change. Different strategy at $300m ARR than $20m in ARR. I like to see at least one promotion. That may be enough, as long as they are a true manager. But if they stumble with the answer, can’t answer it honestly … they’re not a real manager.
• Do you currently hold a quota or commit? Why or why not?  If he or she hasn’t held a quota in a while, I don’t like it. Why did you get “promoted” out of a quota-carrying job? Probably because you weren’t that great at carrying a quota.
• Who are your best 2-3 reps ever? And why? Will they come with you?  Not unique to BigSaaS Co candidates. But even more helpful here. If they won’t come, Houston, we have a problem. If the question isn’t answered with absolute ease and fluency, Houston, we have another problem. And why will these reps excel at your company?  Too often, folks from Big Logos just say they were “hire some recruiters”.  They often don’t even know any.  Pass.
• Why did you leave? There are many good and fine reasons to leave. But if they struggle to answer crisply and coherently — that’s a flag. There should be clean, clear, obvious reasons To Leave Something So Great.
• Will your boss say you’re one of their best hires ever?  Really their boss should. If not, we may have a problem. If the candidate stumbles here … I’m pretty sure she was lucky. Not great. Get some stories here too.
• What would you do first?  The Big Logo candidates often just don’t know.  Because they never had to figure it out.
• Why do you really want to work at an early-stage start-up?  The answer often isn’t genuine.  Pass on those ones.

Dig in more along these lines. Don’t get suckered into the ride they were on.  In fact, make 100% sure you’d hire them even if they didn’t work at That Hot Tech Startup Before.

No matter what, make sure this candidate really did it. Not just knows how to talk the talk. Because all managers know how to talk the talk at Big Successful SaaS Companies. All of ’em.

It will help you find out if that seemingly terrific candidate (on paper / LinkedIn, at least) from that Super Successful SaaS Company really did it. Or — was just lucky.

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