The #1 Best Hack to Making Sure a VP of Sales or Top AE Will Work Out

We’ve talked a ton on SaaStr over the years on how to make sure your VP of Sales and top hires really work out.  That they are the right ones.

We can pretty much summarize a lot of it into the following:

• Your VP of Sales should have lots of experience selling at your average ACV.  A great VP of Sales that has mainly sold $100k deals just isn’t going to make it at a $5k ACV start-up … no matter how strong they otherwise are.   Whatever your target ACV is for next year, that should be the #1 area your VP of Sales hire is good at.  Being good at a certain deal size also means you know how to have the velocity, the pipeline lines, the opportunities needs, the hiring needs, etc. for that type of sale.
• Your VP of Sales should have hired at least 2-3 quota-hitting reps before.  Make sure they really have.  Go talk to at least 2 of the reps they hired that hit or exceeded plan.  See if it’s all really as it seems. If your VP of Sales candidate knows how to source and hire 2-3 AEs and make them successful, they can do it again, even at a much larger scale.  But if they’ve never really built at least a small strong team themselves, you are taking too much risk here.   Inheriting a team, or being given a team, but not having recruited it yourself doesn’t count.  Be careful hiring someone who was a team lead really, but didn’t hire their team.
• Your VP of Sales should have 1-2 reps they’ve worked with that want to come with them to your company.  Being a VP of Sales is about management and recruiting and building great teams.  A good VP of Sales candidate, even a true stretch candidate, will often have at least 1-2 of their top reps from their last role that want to join them at their next one.  Ask who they are.  And talk to them to make sure it’s … true.
• Your VP of Sales should have experience at least at the stage you’ll be at next year.  Not every VP has to have true “start-up experience”, but it’s super risky if they didn’t at least work for a while at the stage you’ll be at next year.  If you’re at $5m ARR, and next year plan to be at say $10m ARR … it’s OK if the smallest company they’ve ever worked at is $10m-$12m.  You’ll be there soon enough.  But if the smallest start-up they worked at was say $40m ARR … it’s not going to work out.  A bit more on this here.
• You have to believe.  Do not hire a VP of Sales you don’t 100% believe in.  This sounds silly, but I see this mistake so often.  Especially with VPs of Sales with great-seeming resumes and on-point domain expertise.  Hooray, they worked at Slack.  Yes, it’s a great company.  But if deep down you don’t 100% believe in them … don’t make the hire.  A bit more here.

Ok those are the mandatory requirements for a VP of Sales to work out.

Now let me add a 6th.  It’s not mandatory but it super helps.  It helps a lot.

• It helps a ton if the last product they sold … was harder to sell.  Sales is always hard.  But coming from say, a product with huge brand lift to one that’s harder to sell … those VPs of Sales almost always struggle.  Come instead from a really tough sales environment, into one just a little less hard though … and they often just fly.  It’s like a weight has been lifted from their shoulders.

I’ll give a few quick examples.

Last week, a VP of Sales I know joined a SaaS company at $3m ARR, doing well, but without a true repeatable sales process.  A good one, but not a rocketship yet.  But he was sooo happy his first 30 days.  Why?  He’d never had so many leads or happy customers before.  His last job as VP of Sales was even harder.  He had so few leads, he had to spend half his time managing outbound.  And the customers weren’t nearly as happy.  So yes, this VP of Sales’ job is still hard.  But with more leads and higher NPS than his last role, the wind was in his sails.  In fact, he decided to postpone hiring an outbound team to just focus on the lead flow they already had coming in.

Another fun example is from Sam Blond, now CRO of Brex.  His second sales job was with us at Adobe Sign / EchoSign, and he joined in a tough time.  But he’d just come from his first sales job — at a product that was even harder to sell back in the day, cloud financials.  Within 90 days, he was our #1 rep.  He’d already learned how to sell something that was really, really hard to sell. Now he only had to sell something that was really hard to sell ?

This is just a simple hack I don’t see folks using enough to bend the odds that a VP of Sales will work out.  But when you find a VP of Sales candidate you really like, try to figure out if their last job was harder.  A product harder to sell.  With less support, fewer leads, less reference accounts, lower NPS, higher churn.  If so … that gives them just a chance to run at your start-up.

And run they probably will.

And some advice here for folks taking that first VP of Sales role: