Don't Hire a VP Sales Without These 4 Traits

Hiring a VP of Sales can be a tricky process as most good salespeople know how to sell themselves. Seeing through this well-presented persona is one challenge, but for many startups, hiring becomes even more complicated due to the fact their organization might be at a different level of sales maturity then what a top VP is used to.

In addition to all those tactical hands-on skills, there are some traits that we’ve seen time and time again in GREAT sales leaders. And to help CEO/Founders looking to hire a VP Sales we’ve outlined the top 4 traits to look for when seeking a GREAT vs GOOD VP of Sales.

A Reinventor 

Before every new search, we engage our clients in a “requirements gathering call” to understand the role beyond the job description and get the scope of the opportunity or the problem the person is being hired to champion. During these calls, we ask “are there any specific companies you want to see people from?” While we understand that many employers are attracted to candidates from competitors, our experience has shown us that many of the top sales leaders have reinvented themselves multiple times throughout their careers. 

While some call it ‘chasing money,’ sales leaders are wired to be opportunistic. Being opportunistic often translates to moving from one software category to another in the early days of that new market. That’s where the big opportunities are, after all! And the more times a sales leader has reinvented themself by figuring out how to sell the value and vision of a new product category, the more likely they are to be successful selling your solution and exceeding targets.

Underdog Attitude

If they are a song, they are the B-side. If they are a brand, they’ll be on the lower third of the grocery store shelf. If they are on the Gartner Magic Quadrant they are a Visionary (or hoping to be one.) The underdog sales leader is the one who goes up against other well-known leaders regularly. The one who has to be smarter, faster, and more nimble to close the sale. 

They beam when sharing how they won a deal against their biggest competitor. In one case, we spoke with a VP Sales of a US-based company, and that VP specifically asked me to try to recruit one person whose name they knew because they were tired of the number of times they heard this name during head to head deals. This is the dogmatic and scrappy determination startups need to close the big deals that propel the brand forward. Never underestimate the underdog as they have the hunger needed to do less with more and succeed.

Employee Loyalty

The best Sales Leaders are likable and have a network of people who want to work with them again and again. Where they go, top junior talent follows. People who have worked for them have benefited from being part of their team and will be ready to join them on their next adventure. 

Given how hard it is to hire great salespeople, having a VP Sales that can also bring along proven talent is a huge advantage. As more deals start to close and the team starts to expand, having top talent waiting in the wings to join your organization and build upon the success of your VP is immensely important in reducing ramp up time and departmental churn. 


Another true story; a few years ago one of our candidates was scheduled for their final interview which was a presentation of their 30-60-90 day plan in front of the SLT. When the Founder/CEO called us after the presentation, she said one word: HIRED! When we asked the reason, our client rattled off all the right reasons why anyone would want to hire a VP Sales, but then at the end, they added “...and he was ready for anything.”

Turns out, when our candidate was setting up their laptop and trying to connect to the video system, there was a hiccup with the cables, but this was no problem for our candidate who had come prepared with every possible type of cable and adapter for exactly this reason. Shit happens and top sales people need to be in a position of readiness at all times. 

Outcome Oriented 

In my 30 plus years of meeting and interviewing software sales leaders, one of the obvious traits that stands out and moves someone from the GOOD list to the GREAT list is their consistency of seeking an outcome. They are always advancing a process forward.

  • “Martyn, I’m interested in this opportunity. What do we do next?”
  • “Is there anything else you need from me to advance to the next step?”
  • “Do I have your endorsement as a candidate for this position?”

A disciplined and consistent format to a candidate’s business conversations is also the approach they will take to the company that hires them - and it’s not an easy trait to maintain. Generally, it’s ingrained in the DNA of the person. They are focused on outcomes, not outputs.

Not sure where to begin when trying to differentiate those good vs great sales people? Book a free consultation with Martyn Bassett to discuss the current sales landscape and marketplace.