Four Questions to Ask to Nail Your First Sales Hire

By Kristina Bergman

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The CEO as a salesperson does not scale. To ensure your startup can, use these four key questions to hire an effective sales leader.

Canada just experienced its top quarter for venture capital investment of all time, with $2.7 billion invested across 175 deals. The numbers speak to an extraordinary time in Canada’s innovation sector. It is also evidence that many entrepreneurs are successfully navigating the growth of their businesses from seed to scale.

But as we congratulate CEOs for what they can do, we must also celebrate an entrepreneur who takes a step back, hires intelligently, and empowers people around them to get even more done in the areas of HR, product and, most importantly, sales. Of course, CEOs must always be selling––or “always be closing,” as the startup adage goes––but there is just one problem: The “CEO as a salesperson” model does not scale.

That is not to say that the CEO is not an integral part of all companies’ sales processes. They are. But inevitably, there is a transition phase that companies go through where the CEO must begin to hire an executive team around them. The first sales hire is arguably the most critical role to hire for––and one that many startup CEOs do not get right the first time around.

There are many sales leader archetypes, from caretakers to closers, and there is no magic formula for choosing the perfect fit for your startup. But as I have worked for tech giants like Microsoft, scaled my own startup (before exiting), and worked closely with portfolio companies as an investor, I have found four considerations especially useful as a guide for teams hiring this critical piece of the executive team puzzle:

Is this person a player-coach? 

The business and sports world nomenclature has many overlaps, but perhaps the most important shared term is player-coach. In sports, a player-coach is a member of a team who simultaneously holds both playing and coaching duties. While the role is uncommon, in scaling startups, it should not be.

In a hockey game, it might be shocking to watch a coach grab a hockey stick, jump off the bench, and join the action. But when it comes to building out a sales function from the ground up, someone who is just going to hire a team and watch them in action is not enough.

You need someone who will actually go and sell along with these team members. You want to look for someone who has done zero to millions in revenue growth, has written their own sales playbook, set up a CRM, and hired their own Sales Development Representatives (SDRs). But you do not necessarily want to bring in a big shot who has already been a VP at a ‘Big Tech’ company. They will be too used to being “management.” They have forgotten what it is like to get their hands dirty, which brings me to the next key question you need to ask.

Are they execution-oriented?

What does it mean to be execution-oriented? It means this person will run through walls until they figure out how to sell your product and who to sell it to. In enterprise sales, there can be a million internal stakeholders in a business, and your new sales hire needs to be willing to bang down doors to find out who the decision-makers are.

Early-stage sales is about building up relationships to the point where the customer has a similar level of faith in the salesperson as they would have in the founder or CEO. Now, the founder CEO may come in to help close the sale but they are not actually running the process and building all the relationships along the way. First-time salespeople often fall down because they are expecting a certain infrastructure and leads to be handed to them. They expect a fully-baked playbook, but they should be co-creating that with you, the CEO.

Do they have a strategic mindset?

When people think of sales, they often think of someone who is good with people who spends a lot of time building relationships with customers. But a great early sales leader is strategic and owns all of the revenue. They are responsible not just for new sales, but for recurring revenue and customer enablement. Success in this area requires someone who is strategic enough to listen to not just what customers are saying, but to what they are not saying––and understands the relationship between both.

When you have hired someone who can handle responsibility for recurring revenue, they must not only focus on bringing in new customers but must balance that against how your startup can make features more usable to the current clients. They will ask questions like, “How do we make this easier to deploy? How do I make ‘time to joy’ faster?” They will want to help product and engineering teams prioritize what to do next.

At the end of the day, having someone strategic in the head of sales role is about understanding where the market is going and then using that insight to help product and engineering teams balance what current and pipeline customers are asking for. 

Where is the grit?

For me, those three attributes contribute to what I call grit. And one of the most important lessons for me was that early on I did not know how to interview for grit. To gauge this attribute, I have since come up with a list of three things that I believe leaders should want to learn through the interview process.

Firstly, it helps to learn from a candidate what the hardest thing they have done is. This helps to get a sense of whether they have ever pushed themselves outside of their comfort zone––how comfortable they are with making themselves uncomfortable. Secondly, have them talk about a time they have failed and what they learned. This is a check on their humility and their ability to admit failure and accept responsibility. Thirdly, get them to tell me what they are most proud of. This is a chance for them to brag about a big achievement or highlight their so-called superpowers––the interesting nuggets that shape their personality, what kind of team player they are going to be, and if they can they bring a team along through the ups and downs of startup life.

“Sales solves all problems”

At the end of the day, many factors will determine a startup’s scale-up success. One hire will not make or break the future of a company. They will, however, impact a company’s trajectory by generating value or creating chaos. As the popular business axiom goes: sales solves all problems—or at least has the potential to. But only if you have hired the right person for the job.

Kristina Bergman is a Partner at Pender Ventures.