30+ SaaS CEOs Share The Signs Their First VP of Sales … Just Wasn’t Going to Work Out

What it's Fair to Expect -- And What It's Not Fair to Expect

Jason ✨Be Kind✨ Lemkin  @jasonlk

What was the first warning sign your VP of Sales wasn't going to work out?

So perhaps the first SaaStr post that generated a lot of controversy was “If Your VP of Sales Isn’t Going to Work Out — You’ll Know in 30 Days”.  The point of the post wasn’t that a new VP of Sales can get everything done in 4 weeks.  But rather, that you should see improvements ASAP.  1 or 2 new, better reps.  A few stuck deals that finally close.  Etc. etc.

A lot of veteran SaaS revenue leaders protested, but most of them, upon reflecting on it, came to agree the point was right.  A new VP of Sales doesn’t always double sales in 30 days — although it can happen in SMB sales.  But they do move the needle.  They don’t just talk.

As an update to that classic post, I asked founders what were the signs they first saw … that a mis-hired VP of Sales wasn’t going to work out.  I’ve collected them below.  If you think you’ve made a mishire, but aren’t sure, take a look at the list below.  These are warnings signs.

“Instead of learning what was already working and earning trust of existing sales team Brought in the exact sales script and process that worked at their last company Lasted less than 60-days” — Andrew Gazdecki, CEO Microacquire.

The old playbook does help, but every great VP of Sales knows they quickly have to evolve it to any new role.  A mediocre VP of Sales … doesn’t.

“First order of business: let’s buy a Keurig for the sales floor.

Second order of business: never learn the business, pricing, names of reps, or anything else.” – Ryan Doyle, Magic Sales Bot

Ok, I do enjoy the Keurig so not sure I’m there on the first point.  But the second one is spot on. You can laugh, but so many VPs of Sales I’ve seen fail in startups never really understood the business, the pricing, or much else.  Why?  They are just trying to run a process.  That can work sort of OK in bigger companies, when the job is dashboards and pipeline.  But it doesn’t remotely work before $10m-$20m ARR.  If ever.

“Narrow scope lens rather than wholistic lens. Secondarily not metrics focused.” — Paul Tyrrell, Founder, Field Insight HQ

A VP of Sales can fail by only caring about metrics and process, and not the product and distinct customer needs.  But they can also fail if they can’t get their arms around what metrics matter.  More a risk in a very stretch VP of Sales that’s never owned the overall ARR / bookings number.

“Can’t source and/or close a single deal” — Julien Codorniou, Felix Capital

OK, don’t laugh at this one because it’s real — and common.  It can take 2 different forms in my experience.  If you hire a VP of Sales too early and hope they can jumpstart sales, it’s often too early to bring them in.  They close nothing.  And almost worst, and more insidious, is the VP of Sales who joins something with some momentum — that doesn’t add anything to that momentum.  They claim credit for everything happening, but don’t add anything to revenue.  Their job is to tilt the curve.  Not barely maintain it, but with more expense and resources.

“Prev jobs all < 2 years and trading off those logos . 1- 2 times can be fit/ other co issues. No long term employment = better at selling themselves than a product or service. Always a deal that’s “about to close”, not enough top of funnel activity.” – Aanand Radia, Education Investor

A great VP of Sales probably does have to have stayed one place for long enough to get promoted, hire their first team, and see the full cycle.  That takes 4 years.  More here.

1. Doesn’t recruit any of their own people

2. Promises unrealistic deals/customers early

3. Their first sales pitch. If you talk 10x > than you listen, easy to know it won’t work out — Jonathan Lacoste, Space VC

Any great VP of Sales — job #1 is recruiting.  If they can’t recruit ASAP — in their first 30 days — it’s usually hopeless.

“Ability to recruit top talent and has a network that follows is the #1 signal. Talent is the bottleneck for all exec functions and early leading indicator on success or failure is recruiting gravitas.” — Joel May, Bridgegate

An amplification of the prior point, but a good one.  50% of the job of a true VP is recruiting.  And VPs of Sales have to recruit more talent than any other role.  So they are always recruiting.

“When I had to call the police to go to his house and see if he was alive/missing/ok…and if the rental car he had was in one piece. True story. He seemed so promising…until he didn’t.” — Ben Block, CEO GozAround

This may sound like a story that can’t happen to you, but it’s a reminder to Finish. Your.  Diligence.  Folks these days are hiring faster than ever, and they are skipping reference checks routinely.  Even worse for a VP of Sales, they aren’t calling past hires and a customer or two.  You have to.  Or you may well get Catfished by a VP of Sales that talks the talk, but can’t or won’t walk the walk.

“Can’t Hire.”  Heidi Bullock, CMO Tealium

We said it above, and we will say it again.  But a VP that can’t hire isn’t a real VP.  And most especially a VP of Sales.  Half the job is hiring great sales execs.  If they haven’t brought on 1 great sales rep at least in their first 30 days — they never will.

“Focus on empire building versus our seeing customers and closing ACV.” — Adnan Chaundhry, EVP Sales, Slack / Salesforce

If a new VP of Sales doesn’t start talking to customers their first day on the job, at least joining a call or two — you’ve got problems.

“First milestone check (4 weeks) when it was everyone else’s fault for non delivery. And even earlier conversation was about what ‘you’needed to do as a company and not ‘we’.” — Susan Burton, CEO Classlist

The blame game starts early for a VP of Sales that isn’t going to make it.  You hear complaints about the VP of Marketing, Customer Sucess, the product and more rapidly.  They are always excuses for not hitting the number.

“Sells snake oil to customers then tries to ask R&D to deliver and ops/cust success to support for free.” – Harry Labana, Managing Director, Goldman Sachs

A little tiny bit of this is part of enterprise sales.  But a new VP of Sales who tries to get points on the board but selling features that don’t exist … that’s a huge red flag.  They won’t work out.

“When he told our board (in his first meeting) that we should consider setting our price point at $50 per month. (Our ARPA was ~$1,200 at the time)” — Ed Laczynski, CEO Zype

The new VP of Sales that doesn’t respect what already is working is a huge flag.  The best ones double down on what it is already working, just tune it up and do it better.

“Ability to recruit top talent and has a network that follows is the #1 signal. Talent is the bottleneck for all exec functions and early leading indicator on success or failure is recruiting gravitas.” – Joel May, Exec Recruiter

Yup.  Again, it’s a recruiting job more than anything else. Hiring a VP of Sales without at least 2 good reps ready to follow here is super risky.

“Couldn’t get the name of the product correct. Never logged into the site (didn’t know the URL). Didn’t spell team members names correct. Openly yelled at PMs and Devs. Oh, and never sold anything.”  — Katie Robbert, CEO Trust Insights

Sales leaders that never use the product or log into the site is just too common.  They shoot from the hip.  Maybe OK when you have a huge brand backing you (not OK, but maybe it works sometimes).  Fails at a start-up.