Hiring a VP of Sales isn’t new, but the conversations have evolved as the world has. SaaStr’s own Jason Lemkin shares the top 10 mistakes he sees during the hiring process during Workshop Wednesday, held every Wednesday at 10 a.m. PST. 

Jason has written about the cheat codes for hiring VPs of Sales since 2012 and realized it was worth a deeper dive. 

Read the Ultimate Guide to Hiring a Great VP of Sales ebook or What Makes a Great VP of Sales and How to Hire One blog post. 

The last 18 months have seen the biggest changes in the VP of Sales in his SaaS career. We’re still learning what world we’re in — some people interview over Zoom, some are focused on how to build teams in the current age, and many are dealing with a weird overhang from the SaaS explosion of 2021, quiet quitting, layoffs, and team turnover.  While this topic isn’t new, you want to avoid getting this hire wrong. So, let’s look at the top 10 mistakes Jason sees in the VP of Sales hiring process. 

1. Hiring a VP of Sales Who Never Really Understands Your Product During the Interview Process

You can’t really learn on the fly, not in most spaces anyway. This is the number one mistake founders make when hiring a VP of Sales. 

“Never, ever, never hire a VP of Sales who doesn’t understand your product during the interview process,” Jason says. This is one of the top reasons they have imploded over the last 24 months. 

Many have hired too quickly or hired over Zoom. Founders are attracted to folks who know the sales process and can talk about recruiting, NRR, GRR, and ARR. But they never understand the product. Sometimes, you can be lucky and hire a VP of Sales who knows your product, like Jason’s first great VP of Sales hire, Brendon Cassidy, who worked at LinkedIn and was a customer already. But for a non-sales or marketing product, a tech or development product, or products that are more complicated than the last sale are likely to implode because they can’t learn it on the fly. 

It’s not all about process, joining calls, talking about contracts, and giving a bigger discount. SaaS products are brutally competitive, so if you don’t know the product, the customer will go to someone else who deeply knows how to solve their problem. Some might challenge this idea and say, “Why should I learn before I start?” Because you can’t succeed if you don’t learn before you start. Use Google or attend weekly webinars with the company, read the content on their website, or try out the product. You can get up to speed by diving into the content. 

2. Hiring a VP of Sales with No One Lined Up to Follow Them

You have to do the work here as a VP of Sales. Almost no one does real reference checks anymore. All great VPs of Sales are spending between 25% and 50% of their time recruiting. They might be passively recruiting, following up with people, and building relationships with people from past companies. 

Any great VP of Sales knows other VPs of Sales and up-and-comers because sales is usually half the headcount in a startup. The last thing a VP of Sales wants to do is start without a team. If you interview someone and ask how they’ll get candidates, and they say they’ll get a recruiter. There’s no way. 

You can hire them as an AE or another role, but they can’t be a sales leader if no one will come with them. 

3. Hiring a VP of Sales Who Actually Doesn’t Want to Sell Themselves Anymore 

It’s understandable not to want to sell anymore, but it’s not what 99% of startups need. This mistake is newer, but it’s not new. 

You can read a classic SaaStr post called The 48 Types of VP of Sales. It talks about Mr. and Miss Dashboard, who want to hit reset and watch the dashboard. It’s been a persona forever, and it’s one issue. 

Two things accentuate this related issue. 

  1. How long we’ve been doing SaaS. People get tired. 
  2. Burnout over the last 2.5 years with all the changes since 2020. 

So many candidates know the language but aren’t willing to sell it themselves or close deals anymore. They want to hire other people to close, and they’ll coach them. But you’ll never learn the product or get good at it this way. You’ll never know the specific playbook or the customer’s pain if you don’t sell it yourself. 

Don’t hire people unwilling to sell themselves for at least the first quarter. If they’re past that point in their career, you don’t want them at $100M or $1M ARR. 

4. Hiring a VP of Sales Who Doesn’t Want to Visit Customers in Person

Some people just want to stay home now, and that’s fine. But they might want to stick with SMB. This is another tell related to the last point, another red flag. 

We’re all comfy at home and doing Workshop Wednesday or in the office, but we’re all running distributed teams at some level. This is one mistake that, outside of SMBs, you have to ask because you can’t hire a VP of Sales who won’t visit customers in person. Not everyone wants to travel or fly to Vegas or NY to meet a customer. That just won’t work in Enterprise or mid-market. 

5. Hiring a VP of Sales Who Doesn’t Want to Close At Least Some Customers Themselves

This is related to point three, but it’s a bit different. You have to close deals yourself to learn. And too many don’t want to close customers. They want to join folks on the team and help them, but they never learn the playbook to closing if they don’t close themselves. 

In interviews, ask them if they want to close any in the first 90 days. You’ll have your answer based on theirs. Some will want to learn the ropes in the first month or carry half of a quota, but for those who don’t, they won’t make the cut. 

6. Hiring a VP of Sales Who Has Gotten Cynical on Startups, Tech, and Sales

This is a newer issue tied to other issues. The Cynical VP has exploded recently. You see it all over LinkedIn with people talking about how they got fired last year, even though they crushed a $7k quota. You see people with eight side hustles, and they’re burnt out. You see people who won’t work full-time unless they make as much as the CEO. 

“I get it,” Jason shares. He’s had the short end of the stick before. Things don’t always bounce the way you want them to bounce. 

He guesses that 30-50% of VPs of Sales are cynical. You need pirates and romantics, not someone who can tell you why their last company mistreated them or they have 7-10 angry posts a week about why they were ripped off. They won’t come in and make the sales process better. It’s a quiet toxicity, and you want to be exceptional. 

The truth is that the cynics need to get out of the game. Sales is hard, and every month and quarter, the dials go back to zero, and the goal goes up. Don’t hire someone that’s actually done but needs a job. 

7. Hiring a VP of Sales Who is Constantly on Social Media, Especially LinkedIn 

A little bit of this is good, but 7x a week? Stay away. “I’m not a huge fan of social selling,” Jason says. But promoting yourself to a certain level is helpful, like one to two insightful posts a week that attract folks to you. 

That can be great if you’re great at it, but the folks posting twice a day want to be influencers, and you’ll see them bragging about the number of followers they have. But how much money do you make on LinkedIn? 

Folks constantly posting on LinkedIn are bad for a VP because they don’t want to do the job. You don’t need an influencer at your company. 

8. Hiring a VP of Sales Who Really Wants to be COO, CRO, etc. 

A VP of Sales has to love closing. Period. CRO is not a place to escape sales. This isn’t a new mistake, but it has accelerated in the last couple of years. 

A VP of Sales has to love closing deals, exceeding the plan, crushing the quota, or building a great team. They love the game of the hunt and beating competitors. You want closers. 

To simplify the job, half is recruiting, and half is doing everything you can to close. You don’t want them in operations, customer success, onboarding, or renewals. If the product is good, someone else should renew it, and it shouldn’t require massive amounts of sales efforts to renew. 

There are a couple of exceptions here. 

For instance, when you have a hole to fill. If you don’t have anyone to do onboarding, the head of sales can fill the gap. 

Another is when someone wants a bigger title. You have to be careful, though. Jason’s rule is that an inflated title is only ok if they earn it in the next 12 months. If they’re not really VP of Marketing and are actually a director, but they’re so good, you can give them the title if they ask for it. 

But be very wary of someone who wants to do more than sales. 

9. Hiring a VP of Sales Who Hasn’t Been a VP of Sales in Quite a While But Wants to “Get Back to Sales.” 

A little break is good. Someone who stepped out for the family and is also a rockstar should always be there. You should have one. 

But the ones that have putzed around, golfed, backpacked, or spent a year and a half on LinkedIn or as a Fractional CRO don’t want it. It’s too hard. 

Sales is a hard game, and being the boss is even harder. At least a great AE can just hit quota again and again and sometimes get better at it. Sometimes, the best AE dials it in. But the VP of Sales is harder. 

There’s nothing wrong with a few months off to refresh, but someone who went off to product for a while or built sailboats won’t get back in the game. If they wanted to go for the brass ring, they wouldn’t have stepped off the stage. 

10. Hiring a VP of Sales That You Wouldn’t Hire if They Hadn’t Worked at ________. 

There are so many great SaaS veterans now that it’s blinding folks. This isn’t new, but it has accelerated because the number of SaaS and Cloud leaders has accelerated. 

A few years ago, Datadogs wasn’t huge, and CloudFlare was tiny. There are so many great logos to hire from. 

So, here’s a challenge. 

Place your hand over LinkedIn and be honest. Would you hire them if they hadn’t worked at Notion or Shopify or Datadogs or whatever your dream company is? There’s nothing against these iconic and successful companies. 

But if you interview someone and they don’t know the product, and they don’t want to be a sales leader anymore, they’re breaking a lot of these ten rules. If you’re not sure, don’t make the hire. 

In the early days of SaaS, Salesforce was the only logo because it was the only multi-billion dollar SaaS company. Now, there are dozens. 

If you keep at the hiring process, you’ll convince fancy logos to join you. But do this exercise to see if you’d still hire them if they didn’t work at those places. Use these ten points to help you hire a great sales leader, and say no to the rest. 

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