Your First Sales Hire Will Make or Break Your Company

Posted by Ryan Neu

Mar 12, 2013, 10:35 AM

You have a startup, some sort of Minimum Viable Product and maybe a few bucks in angel or seed fundingmark_roberge.

"You are ready to make your very first sales hire. Who should it be?"

Last week in Dublin, Ireland, I had the chance to hear HubSpot's Mark Roberge give a talk about how to build a predictive and scalable revenue model. Mark has successfully built and scaled HubSpot's sales team to over 150+ sales reps (almost entirely inside sales).

During his talk, Mark walked through 4 different sales personas and asked the audience who they would hire as their very first sales rep. 

There is no right or wrong answer but his question opened up some great discussion. For each persona, I've summarized the pros and cons, as identified by the audience. Here are the 4 sales personas:

The Old School Exec

Persona: The Exec is an industry veteran. He has 25 years' experience at your company's biggest competitor and is willing to join your company as the first hire and VP of Sales. 

Pros: He has a huge Rolodex (and Rolex) and can certainly help bring in some big deals and partnerships. He is trusted within the industry and his name will definitely lead to some early success.  

Cons: He hasn't gotten his hands dirty for two decades. He led a huge sales team at his previous gig and is detached from the day-to-day world of hitting the phones, recruiting college grads, and traveling to meet prospects, attend trade shows, etc. He comes at a price but that is not the biggest reason why you should be wary. The Exec is not the ideal first hire because he is past his "bootstrapping days". This hire may make sense down the road once you've built up a foundation but this is not the ideal first sales hire. 

The Entrepreneur

Persona: Young and ambitious, the Entrepreneur recently had to call it quits because their start-up was not able to raise a Series A. Now the Entrepreneur is ready to bring her talents to your company.

Pros: She is clearly driven, smart, creative, and up for a challenge. The Entrepreneur will do whatever it takes to get the job done. She will have no problem doing entry-level tasks as well as jumping into C-level meetings. The Entrepreneur is versatile. 

Cons: Can you keep her excited and entertained at your company? Attrition is the biggest concern with this hire. By nature, the Entrepreneur enjoys new challenges and a fair amount of risk. As you build up your sales team and as your product stabilizes, can you keep the Entrepreneur excited? This is definitely an appealing persona but you will need to get creative with incentives. Make sure that you understand what actually drives this persona--so that you can keep them. 

The #1 Sales Rep 

Persona: The Sales Rep was the #1 sales rep (out of 100 reps) at a company in a different industry. He is fearless and doesn't like to lose. 

Pros: He's proven that he is a winner. Prior success is a great indicator of future success. Top reps at their former company are likely to succeed in their current role. 

Cons: Even though he succeeded at his previous company, remember that you have a different sales process and sales cycle. Will he be able to abandon his "transactional sales" habits and adapt to your "consultative sales" approach? Be careful. Prior success is a great indicator but you should take a deep-dive to ensure that he will be able to learn your sales process. As you review the Sales Rep, make sure to look for coachability and humility. This is a tempting option, rightfully so, but make sure to do your diligence. Also be cautious that this top performer is accustomed to making a lot of money. Be ready to come up with a competitive compensation package, likely including a lower fixed salary and higher variable comp and equity plan.

The Mid-level Manager

Persona: The Manager was recently promoted from a sales role to manage a team of 5 in a similar industry. She consistently hit her quota as a sales rep and has less than a year's experience managing a team. 

Pros: The Manager is stable, driven, and has shown success and demonstrated leadership. The Manager has not been managing for too long, so she is not far removed from doing the grunt work. She'll hit the phones, close business, and will be able to manage the team as the company grows and evolves.

Cons: During Mark's presentation, the audience had very little objection to this persona. It was clear that the audience thought that the Manager was the best fit for the first sales hire. To play devil's advocate, I would caution that the Manager has some flaws. She was a solid performing rep, and became a manager but where is her fire? She didn't start her own venture, like the Entrepreneur and she wasn't the top performer, like the Sales Rep. Make sure that the Manager is able to excite her team and make them fight for a common cause. 


Who would you choose as your first sales hire? For those who have built a sales team, how did you make your initial hire? Did it work out? Share below!


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