Mistakes Founders Make When Hiring Their First Salesperson

By Fernando Berrocal

Finally, your Minimum Viable Product (MVP) is finished. There's some seed money in the bank, maybe possibly a Series A. You're eager to see if your product sells quickly. It's time to recruit your first salesperson. This is a significant step forward. The correct decision may set the stage for the rocket-ship sales chart that every entrepreneur dreams of. A bad decision might lead to its downfall. Use this knowledge to assist many businesses with this crucial initial sales job choice over the years. When it comes to recruiting their first salesman, many entrepreneurs make the following errors.

mistakes founders make hiring first salesperson

The first mistake is hiring a top executive. “Yes! We just hired the director of sales at the public business we want to take over.” This means that trouble is on the way. Brand new startups are prone to being greedy and pursuing the industry's big-name leader, here's the problem: this leader hasn't sold in years on the front lines. When she initially starts working for the business, her first query will be, "Where is my assistant?" Someone who is closer to the action and willing to roll up their sleeves and get their hands dirty is required.


The second mistake is that it gives industry experience too much weight. “What is the most important criterion you are searching for in your first sales hire?” I inquire. “Experience in our industry,” says the founder of a startup. The above response is given to me 99% of the time. It makes me uncomfortable. The solution appears to be reasonable. Domain experience is unquestionably easy to evaluate. Startups, on the other hand, frequently place too much importance on candidates' industry expertise and overlook actual flaws in their skills. The majority of attendees were from outside of the marketing software industry, and even outside of software and technology in general.


The third mistake is undervaluing experience with go-to-market strategies. This strategy is generally not created when your first sales hire joins the startup. What number should they dial? Big corporations? What about small businesses? Should they focus on closing the C-level decision-maker or obtaining a free trial from the end-user? Will they sell directly or through a route of distribution? Will deals need to be performed in person or may they be done over the phone? Most sales leaders will just try to duplicate their prior employer's go-to-market approach. Then it worked. When deciding on your startup's optimal go-to-market plan, think about your buyer, your product, and your corporate strategy. Make sure your initial sales hire has prior expertise with that strategy or is eager to learn and adapt.

The 4th mistake, ignoring experience with sales process development. “Yes! We recently recruited our Fortune 500 competitor's best salesperson. Out of 1800 salespeople, this was ranked first. She's going to destroy this place.” I concur. This salesman has a lot of potential. When she comes to your business, however, these will be her first questions:

  • “Can you tell me where the pitch deck is?”
  • “How should I go about selling my product?”
  • “Where can I get a list of the top ten objections and how to deal with them?”

Lastly, the last mistake is that rather than hiring a "consultative salesperson" hire a "product pitcher.” The most beneficial outcome of your first thousand sales calls, will not be the early clients or income generated. Instead, it will be the abundance of market input, which will help your team to better grasp your customer persona, iterate on your product, and polish your market message. Unfortunately, many salespeople will use these initial conversations as an opportunity to bombard the prospect with as much information as possible about the product and its attractive qualities, a strategy we term "show up and throw up". 

mistakes founders make hiring first salesperson



There's a good chance that your features and messaging aren't exactly perfect. When the salesperson is unable to engage the prospect, he will throw up his hands and declare, "It's not working." The most important question is “why?” A consultative seller will use the first sales calls to learn more about the potential buyer. They'll learn about their objectives, the method they'll use to achieve these objectives, and the obstacles they'll face along. A consultative seller will be able to return to the team with the same "it's not working" response but will be able to explain why. As a consequence, the business may continue to fine-tune its strategy and improve the product/market fit even further.

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