How and When to Hire Your First Sales Rep

Chase Norfleet
Chase Norfleet



A company starts with an idea and a founder. As the idea gets nurtured and fleshed out, developers and marketers come on board to bring it to life. Eventually, what was once a glimmer in a visionary’s eye is now a real product, ready to be sold.

But who’s going to sell it? In my experience, a company’s first sales hire is usually a marketing and/or sales executive tasked with building demand from the start. But eventually, a dedicated sales rep will become a necessity.

Who you choose to bring on board to fill this role is an incredibly important decision. A first sales rep isn’t the same as just any other sales rep. They need to possess unique qualities that might not be easily found in the market. This is why time is of the essence.

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How Soon Is Too Soon?

A new company needs to start drumming up interest for its product before it’s ready to ship. With that in mind, I think a company should hire its first rep in advance of the product launch date.

How far in advance? That’s determined by the complexity of your product or service. If it will require a significant amount of product training, it’s probably wiser to hire your inaugural rep early -- maybe six months out.

Hiring sooner rather than later also gives your new rep the chance to familiarize themselves with the market, gauge interest, and build relationships with potential customers. That way, when the product is ready, they have some prospects already lined up. With a few months of prep time under their belts, it’ll be much easier to hit the ground running.

Finding the Perfect Fit

Your first sales rep will set the tone for the rest of your sales organization. That’s why it’s important to hire thoughtfully and carefully.

There are a few characteristics and skills you should look for when searching for your initial rep:

  • Industry experience. In addition to solid selling fundamentals, the candidate should also have experience working in your specific niche. For example, if I was hiring the first sales rep at Jitterbit, I wouldn’t just hire any technology salesperson -- I would look for someone who had specifically sold integration solutions before.
  • Startup experience. Working in a startup is drastically different from working at an established company. Seek someone who is used to the chaos and the fast pace that come along with a brand new organization.
  • Self-reliance. Reps selling at large companies have many resources at their fingertips -- marketing material, trainers, coaches, and maybe even a sales enablement team. A rep at a startup doesn’t have any of these luxuries, so they need to be comfortable wearing multiple hats and getting things done on their own.
  • Ability to scale business. Does this candidate have a track record of growing business for a specific product or service? If so, give them preference in the hiring process.
  • Familiarity with buyers. Look for someone who has sold to your target buyer in the past -- both in terms of industry and size of company. Someone who is used to selling to mom and pop shop owners might falter when asked to make deals at the enterprise level.
  • Culture fit. Startups are high-pressure places with only a handful of employees. If this person doesn’t gel with the fledgling company culture, it’s going to make closely working together all the more uncomfortable.
  • Comfort with risk. At a small company, a sales rep is likely to be on a 50/50 split salary and commission compensation plan. Ensure that this excites instead of discourages.

Once you find the person who fits all of these criteria, hire them and get them in the trenches -- even if your product isn’t ready yet. Are there trade shows you can send them to to start making contacts? Perhaps you can nudge them to join a choice number of LinkedIn or other social media groups and start participating. If you’ve hired the right person, they’ll be hungry to get in the game.

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Topics: Sales Hiring

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