How to hire the right salesperson

You’re starting to see success. You’ve achieved product-market fit and you have a handful of customers that not only love your solution, but use it regularly. 

However, you know that founder-led sales only gets you so far. You’re going to need to hire a sales team to bring in revenue and scale up to the next level. 

The problem is that hiring the right salespeople, at the right stage, is not always an easy task. So how do you ensure you’ve attracted and hired the best candidates to help you grow your business? Who do you make as the first hire?

We’re back with Brogan Taylor, VP of Enterprise and Strategic Sales at Freshworks, Brian O’Reilly, VP of Sales, Customer Success and Operations at Melio, and David Mackay, former Global VP, Enterprise Sales at Hootsuite & Senior Sales Director at Adobe to learn what they look for.

With their years of experience of hiring and building sales teams across Series A and Series B startups, as well as enterprise companies, they share what qualities to look for in your first key hires and how you can assess – and validate – the candidates’ claims of success.  

How do you define who the first key hires are? And how do you determine their suitability?

Bringing in a few, young hungry sales reps to add firepower to your sales efforts is certainly a low risk investment at your earliest stages.

However, our panelists agreed that by starting with some type of senior leadership figure who has vision and experience pays off in the long run. It’s expensive up front, but the ROI is higher, commented Brogan Taylor commented. He said, “It’s very easy to go test the market, with founders or leaders remarking ‘I’m going to go hire my first salesperson and we’re going to see how it goes.’

“If they’re just kind of spinning out there by themselves, trying to figure it out on their own, it generally doesn’t work very well. So, to the best of your ability, try having that executive level vision in place and start to execute on it before you go staff around it.” 

This is particularly true when it comes to handling complex deals – i.e. putting high complex products into high complex environments – remarked MacKay. You need someone with experience. 

So, how do you assess that level of experience for those first, critical roles such as your first VP of Sales, your first Chief Revenue Officer or your first account executive? Set the candidate a task. Have them do part of the job for a few hours – and even pay them to do it. By not setting a task, you’re missing a trick. 

It’s also important to assess ego.  Drawing on their personal hiring experiences, our panelists reflected how folks with very, very large egos – who presented evidence of prior success – actually cause more problems than the value they generate.

What are some résumé red flags?

Job hopping, our panel of sales leaders said, sets off an amber light. “If a candidate has job hopped a lot, that’s a signal for you to go super deep on their motivations for moving and their performance at each company,” commented O’Reilly. 

Today, the average annual turnover of salespeople stands at around 35%. Typically job-hoppers leave because they’re bored. They like a lot of variety in their day to day and you need to mix up the role over time to keep people like that engaged at your company.

Many, though, leave to seek opportunities with better pay or better benefits. Others simply just go to the hottest thing, stay there until it’s done, and then jump to the next hottest thing. 

Consider, though, that it takes around a year and a half to get sales reps ramped and actually contributing – especially in enterprise sales. That comes with significant cost implications, as you invest time and training resources into these individuals. And, as our panel explained, if you see that someone has only been in a company for a year and a half, they never built their territory. They’ve just scratched the surface.

Their advice here? Interview for resilience. Because if you don’t have resilience, even at the most established companies, you might not make it a year.

Salespeople are very good at selling themselves – so how do determine what’s real and what’s not? 

First, look at their track record of success and get into a lot of detail with them on their numbers. Ask them, what did you hit last year? How did you do that? What was your close rate and your opportunities? How did you make the President’s Club? You’ll find that the ‘fakers’ won’t know their numbers. The numbers won’t make sense. 

Second, ask questions to glean a very clear perspective on exactly how they sell. What is their methodology, how do they move deals through the pipeline? What are the things that they do that’s differentiated?

Another tactic is to ask them, if you were to hypothetically reach out to their previous managers, how would that manager rate their performance on a scale of 1 to 10? Salespeople, our panel explained, are typically going to say eight or nine. So then ask them, to get to a 10, what would your manager tell you to do? Keep drilling on that, and you’ll get some really interesting answers.

Lastly, find some kind of back channel on the person to validate their claims. Try and find somebody –  even if they’re a third degree connection – that you can get some inside scoop from.

This blog on hiring your first salesperson is the third in our B2B Go-To-Market blog series. Our previous blogs in this series cover lead generation best practices and our top tips on selling to the enterprise so go check them out.