Your first sales hire

Chase Roberts
4 min readMay 10, 2021


Congratulations! It’s time to hire your first salesperson. All salespeople are the same, right? Wrong. In the same way that a dermatologist wouldn’t do orthopedic surgery or a criminal prosecutor wouldn’t draft your Series A legal docs, salespeople have varying skill sets that are applicable depending on the product you’re selling, company stage, buyer persona, market dynamics, and more. Your first salesperson will help you scale product-market fit, so you want to pick the ideal profile so you can scale most effectively. As a founder, here’s how you should think about identifying 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

Your goal is to identify candidates whose previous experiences fall on this spectrum as closely as possible to where your product lies. Salespeople who previously sold to ”laggards” may not be as successful when selling to “innovators” because each of these customer types require a different selling motion.

When selling into an existing product category, your buyer will already have a process for how to purchase your product: there is a budget owner, a dedicated line item on the budget, designated stakeholders who will qualify this purchase, and there are known buying criteria. The buyer understands the problem they have, and it’s the salesperson’s job to reveal the customer’s process for purchasing new products, satisfy their buying criteria, overcome objections, and navigate to a close.

Conversely, in the case of category creation, the customer does not realize there is a solution like yours to the problems they may or may not realize they have. At the dawn of email, companies were still only looking for fax machines. It took the missionary types to sell email as the next mode of communication.¹ These salespeople are selling a new way of thinking.

The skillset for selling into existing categories vs. those that are emerging differs greatly. The former tends to describe the mercenary type — they are excellent about designing the tactics of a sale, running a clean process, and engaging the resources of the “army” around them — their network, sales engineers, company executives, channel partners — to win.

💡When interviewing these candidates, ask questions about their process and anecdotes about recent sales. If you offer a mock sales interview, they should lead with questions that expose company stakeholders, timing, budget, and the sales process.

When selling into emerging categories, look for missionaries. While it is necessary for these salespeople to understand how their customers purchase, it’s more important to help customers conceptualize the problem that the product solves and motivate customers to believe that they should champion your product internally.

💡Ask these candidates questions that reveal their curiosity and persuasiveness. In a mock sales interview, this person should lead with questions that reveal the problems that your product solves and the measurable impact of not having solved that problem within the organization.

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.

When identifying candidates, find someone whose previous experience is approximately one or two stages ahead of where your company is today (e.g., if you’re a seed-stage company, look for candidates with Series A or B experience). These folks will have experienced what “good” looks like at the next stage and can advise the best practices that should be in place as your company matures.

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?

Great products by themselves don’t make great companies. Founders must also nail market execution, which means sequencing hiring in the right order and finding the optimal candidate given the market and company dynamics. At Vertex Ventures US, we specialize in helping founders turn products into companies — a major aspect of which is developing the go-to-market function and finding the best people. Give me a shout if you’re building a B2B startup at the early stages:

[1] I recognize email is a protocol so this is actually in reference to software for sending/receiving emails, but I hope this makes the point.



Chase Roberts

Investor at Vertex Ventures.

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