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

"The old playbook does help, but every great VP of Sales knows they quickly have to evolve it to any new role."

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.

We 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.

“Didn’t have any relationships with anyone at any relevant companies” — Colin Jordan, CEO Pawtocol

A Rolodex only takes you so far.  It helps in the enterprise, but it’s not critical in the end.  But if a VP of Sales claims they have their industry contacts — and they don’t.  Well, it’s time to move on.

“When they are hired just purely for their network irregardless of culture fit or being a decent human being.” — Kirill So, DeliveryHero

Yup.  See prior point.

“- Negotiates harder in-house than with customers🚩
– Hires only those he/she knows from previous company
– Doesn’t align commission plan w/ company objectives” — Matt Martin, Cofounder, Precise Health Report

A great VP of Sales knows that the comp plan should tie to the ARR goal for the company at year-end.  And they should have enough equity to go long.  If they push for other goals, you have an issue.

“Spends more time on negotiating quota than closing deals” — Mathew Lodge, CEO Diffblue

Yup. See prior point.

“The first ever email that I got to see (via them) had our product’s name written incorrectly.” — Pratekk Khurana

The best VPs of Sales get to be true experts in the product — fast.  And they are always brand ambassadors.

“When they wanted to sell me a pen” — Joshua Ziering, Founder, Aloft.ai

Ok, I do believe in the “Sell Me This Pen” test — when it’s done right.  A VP of Sales should be able to sell you both on the product itself, and on why folks would join the company.  But a VP of Sales that just wants to run an old-school playbook is an issue.

“Wrote a 28 page playbook with call scripts, emails scripts, comp analysis before closing first sale.” — Ishan Girdhar 

This is a good insight.  THere’s nothing wrong with this per se.  It’s the right thing to do when you go to hire reps 4-400.  But if this is what your new VP of Sales is doing their first 30 days, they are all about process over hands-on sales.  They are too Big Company.  You made an error.

“Constantly says “at my last company we…” — Adam Saad

Some of this is good.  But you need to upgrade and update the playbook for each new role.  The last playbook never works 100% at the new sales role.  If you are lucky, 50% of it works. This line suggests an inability to learn and adapt.

“When the VP of marketing outsold the VP of sales, 10:1” — Tim Hayden, CEO YourBrainTrust

This really only happens in SMB and mixed self-serve / sales-driven models, but yeah it’s a sign.  The VP of Sales needs to be at least as good as your VP of Marketing.

“When you have to question if they’re working out.” — Team EPECC

Yup.  This is so true.  Even if you are no sales expert yourself, you should see enough improvements in sales in the first 30 days of a VP of Sales that you know it’s working.  If you don’t think it is … it isn’t.  More time does not solve this.  A tough lesson so many founders have to learn.

“Brought in sales consultants” — Rob Boyle

It might be OK for a VP of Sales to bring in a Salesforce consultant to help with Salesforce, or a little help on revenue operations, in the first 30 days.  But too many agencies and consultants is a big flag.  It’s a sign they don’t actually know how to do it themselves.

“He would get so mad in sales team meetings his face would turn red.” — Josh Buttita

VP of Sales is a tough job.  It requires passion and a challenging combination of urgency and patience.  And the team always believing it can be done.  And showing them it can be.

“As head of product being told “if you can just keep up with me we’ll get to $100m ARR in no time” — Kevin O’Neill, VP Product, Splash

I like this challenge on some level :).  But again, blaming product is a sign of a VP of Sales that won’t get there.  Every startup is feature-poor and had feature gaps.  Product and Eng owe Sales more features every quarter.  But no product will ever be 100% feature-complete vs. the competition.  A great VP of Sales knows how best to work around that, and at least close more deals than closed before they arrived.

“Asks for a product feature to be developed to close more sales quicker.” — Marty, GP, Adventure Fund

Again, some of this as your VP of Sales scales is good.  A lot is a bad sign.

“They don’t connect with your customers when you take them on those initial key client meetings. The big tell is when the customer turns the relationship back towards the C-Level.” – Cris Solomon, Encanto Cloud

This is another great one.  When at the first board meeting I ask a new VP of Sales how one of their top deals is doing, and I push for details, and they don’t know … well, that VP of Sales never works out.

“About the fourth time I hear them trying to tell a customer something utterly contrary to what we do.” — Robert Keith

You can laugh but you have to listen to the sales team’s calls and Zooms — including the VP of Sales.  You’ll be saddened by how many wrong things mediocre sales folks say.  They just make stuff up.  And it’s often wrong.  And that insults the prospect’s intelligence.

“Trying to take on non-sales related responsibilities.” — Nelson Joyce, Cofounder, Tettra 

Another one that is just so important.  The best startup VPs of Sales are just closers.  They just want to close.  They don’t want to own Marketing, or Customer Success.  It’s always a big red flag when they want to own more.  You’ll see.

“If they don’t do something impressive in the first two weeks they won’t do something impressive in the following two years” — Next World Order

Yup.  Giving them more time to put the very first points on the board doesn’t help.

“Blaming de marketing team instead of finding solutions” — Anabella Laya, Founder Acreditta

There are never enough leads.  But blaming marketing doesn’t help.  There rarely are fewer leads than before they started.

“The good reps quit.” — Zach Cusimano SVP People, People.ai

Such an important point.  A strong new VP of Sales moves out the weak performers quickly — usually in the first week or two.  But they focus extra attention on the top closers they inherit.  And make them even better and more successful.

“You ask him to choose a quota number for the year and what he says is lower than his annual travel budget. He then explains he’s not comfortable as an individual contributor. I thought I was on #CandidCamera” — Jeff Kozloff

A VP of Sales that won’t sign up for at least a somewhat ambitious number either doesn’t believe, is scared, or doesn’t know how to do it.  Either way, they aren’t going to work out.

“Excuses, blame not making progress on forced out of her control. Blame the go before you…excuses” — Carlos S

The best VPs of Sales sometimes need to complain just a little bit.  And you need to be there for them.  But they don’t make excuses.  And when they are going to miss the month or the quarter, they let you know ahead of time.  And why.  And how they are going to improve things.

“Leadership Team Meeting for SaaS business, a discussion arose about a product tweak and idea of a pricing model change, Sales VP’s FIRST & immediate comment before we got into anything juicy was about how this would impact sales team members’ compensation packages.” — Ben Hubbard

Sales comp tweaks, accelerators, territories, etc.  This all matters at scale.  But they aren’t the #1 priority for a VP of Sales at a startup.

And let me add a few clear signs I’ve seen of a VP Sales that isn’t going to work out:

• The VP of Sales never truly gets to know the product.  Some of the responses above also hit on this, and I see it too often.  This is especially common when you hire a VP of Sales to sell a product more complex or with different buyers than their last product.

• Spends first 30 days working on process.  Perhaps this is OK at $50m+ ARR … perhaps.  But it’s almost always a sign of someone from a BigCo or without the right real experience that doesn’t know how to sell.

• Threatens to quit.  Leaders just never do this, but I’ve seen weak VPs of Sales do this all the time when they get into a tough spot or fall behind.

• No one good joins them in the first 30 days.  We’re written this before, but the best VPs of Sales are always recruiting.  So they always have at least 1-2 good folks to bring with them.  If they don’t have any — that’s a sign.

• Scared.  VP of Sales is a tough, tough job.  It’s constant stress to hit even bigger numbers.  And sometimes, fear sets in.  Not a bit of anxiety, but true fear.  Fear it can’t be done.  It’s tough, but I’ve never seen a VP of Sales recover here.

If you see hints of these stories in the new VP of Sales you just hired, at least make sure you truly believe.  You truly believe they can do it.

If you do, they probably can.  But if you don’t believe for real.  And you see a bunch of the signs above.  You’ve made a mis-hire.

That’s on you.  Now go fix it.