What was the first warning sign your VP of Sales wasn't going to work out?
— Jason ✨BeKind✨ Lemkin (@jasonlk) February 11, 2022
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Yup. See prior point.
The best VPs of Sales get to be true experts in the product — fast. And they are always brand ambassadors.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Yup. Giving them more time to put the very first points on the board doesn’t help.
There are never enough leads. But blaming marketing doesn’t help. There rarely are fewer leads than before they started.
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.
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.
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.
conflict image from here