One of the trickiest, most important decisions a founder makes is when and how to bring on a formal sales function. While a founder can—and should—lead sales in the early days, their ultimate priority has to be product and company leadership, so handing off day-to-day tasks associated with sales is an important milestone on a startup’s growth trajectory. And a high-stakes one, at that. The right hire can collaborate on product management, unearth audience insights, streamline processes, and accelerate revenue. The wrong hire can bring in the wrong prospects and point the product team in the wrong direction, costing months of company cycles.
So, how should a founder think about bringing on their first salesperson? What is the right profile to hire for your first sales leader, and when do you bring them on?
At Unusual, the operators on our founder support team work with early-stage companies to identify a sales hire who is much more than a salesperson. We like to think of the ideal first sales hire as “a revenue-driving Product Manager.” This is because, in the early days of a startup, the salesperson needs to understand the fundamental needs of the user and buyer, the larger market context, and the nuances of how the product currently meets—and doesn’t meet—the user and buyer’s needs in order to find the first version of product-market-fit. This hire takes the skills they’ve acquired in previous sales roles to learn what the market needs and how the product aligns to those needs. Revenue is initially a byproduct of the quest to find the first version of PMF. You can read our deep-dive on this approach in our Field Guide on the Modern GTM.
We call our founder support team GAP (for “Get Ahead Platform”). It’s Unusual’s team of world class operators from companies like MongoDB, Okta, LaunchDarkly, Segment, AppDynamics, and more—who embed within a portfolio company's organization as contributing, tactical team members, producing deliverables and results that you would expect from a full-time employee.
Two of our GTM operators, Liam Mulcahy and Dakota McKenzie, recently led an exclusive session to unpack these points for the founders and leaders in our portfolio. From that conversation we collected the following guidance. Additionally, you can find yet more tactical resources and actionable tips in the Field Guide, our open source resource for early-stage company building.
Adoption vs. revenue: A founder must solve for adoption before optimizing for revenue. The best time to hire a salesperson is once you have been able to convert interest into users, and then users to customers at least three times in a semi-repeatable fashion, at any average sales price.
Salesperson profiles: Depending upon the nature of your product and the GTM motion, you’ll need a very particular sort of salesperson. The more complex the product’s implementation and sales cycle, the more you should look for enterprise or mid-market reps. The less complex you can look for reps with background on a commercial team. The same goes for your average sale price; the higher it is per user, the more sophisticated your sales hire should be in closing larger transactions with diverse buying committees.
LinkedIn tactics: As you review a salesperson’s profile, look to see if their career shows a steady progression and they’ve had a long tenure at at least one high-quality, relevant company. You can often gauge their past performance by looking to see if they mention an “excellence club” or list quota attainment (by year, not by quarter). You should also think about where those companies were in their own journey when the salesperson was there; were they just getting started? In hypergrowth?
Interview tactics: Some of our favorite interview questions are meant to uncover qualities like their accountability to controlling their own destiny (sample question: “What’s your current breakdown between inbound/outbound?”), their coachability (e.g. “Who was the best manager you ever had? Why? Who was the worst manager, and why?”), and contemporary skills (e.g. “What sales tools have you used and what works for you?”). Where possible, you should ask these candidates to “show their work”, by taking you through a process, qualification methodology, close plan, etc.
Backchanneling: This can be an uncomfortable conversation, but you MUST do it. By talking discreetly with someone who’s managed the sales candidate before you can glean incredibly helpful and relevant information about how much of a fit they will be. To help minimize the discomfort of the conversation, be sure to make it more about the experience of the person who managed them rather than prying for sensitive details about the person themselves. If they’re uncomfortable with providing too much context you can try asking them for responses on a scale rather than providing a thorough report on a candidate.
We hope this is a helpful resource as you approach your first sales hire. For more detailed, actionable resources for your early-stage startup, be sure to check out the Field Guide, and join the company-building newsletter of our Unusual Community for the latest resources and events!