Your first sales hire

Category Creation vs. Known Product Categories

Start by noting whether your product requires category creation or whether it’s a common line item on your customers’ budgets. Since technology adoption typically follows a lifecycle, it’s best to place your product on a spectrum similar to the one below.

An adaptation of Everett M. “Ev” Rogers Diffusion of Innovations Theory

Stage N+1 or 2

Sales organizations offer varying degrees of support structures depending on the stage of the company. Later stage companies have sales enablement curriculum with well-documented sales playbooks, sales engineers to navigate the technical requirements of a prospect, product marketing organizations to provide the most effective messaging, inside sales teams to source qualified leads, implementation teams to ensure successful adoption, robust partner programs influence the likelihood of a sale, and the list goes on. In early-stage companies, the support structure for the first salesperson is usually the founders and an adapted fundraising deck that’s now being used to pitch customers. Drop a salesperson from a later stage company into your startup, and you can expect some angst since they’d be accustomed to more structure and resources.

Athletes vs. Coaches

Coaches build teams, while athletes play the game. If you recruit a VP of Sales (coach) as your first sales hire, do not be surprised when this person focuses on building their sales org (recruiting athletes) rather than closing more customers. I typically recommend hiring athletes initially — these people may have the potential to grow into managers (coaches) but are acutely focused on winning the games in front of them. The primary game you are playing as a startup is customer acquisition, and players tend to advance these wins more rapidly than coaches. 🏆

Domain experience matters

You want your salespeople to be credible in front of their customers, which requires both domain experience and an understanding of the other types of products your customers might assign to this problem. Domain experience also translates into better customer empathy: What else keeps this buyer up at night? What organizational interdependencies does this person contend with? How does my buyer usually make purchase decisions?

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