Hiring its first sales leader is one of the most important things a young company does in its foundational years. Not only does that person build the revenue engine that drives the company through crucial early growth stages, but they also set the culture, values and goals of the sales organization as it scales.
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Early stage sales leaders face massive opportunities, but also huge challenges. Chief among them is finding the right company. Plenty of startups have money, a founding team that truly believes in what they’re doing, and huge reserves of energy and excitement, but prospective sales leaders need to address a host of question marks before joining.

• Will the founders be good partners to the sales organization? 
• Do they understand how to sell, or do they simply want to flip an imaginary “revenue” switch? 
• Are they willing to learn and grow along with you as the revenue pipeline grows? 
• What types of skills and experience do seed-stage companies look for?

Here at Unusual Ventures, we have seen a variety of approaches for startups hiring a sales leader, as well as from sales leaders considering startup roles. Informed by our longtime experience as operators and startup veterans, we have found a few common recipes for sales leadership success. Distilling those common aspects of success is central to the work we do, and we love sharing such practical insights for the whole startup community.

I’ve spent over a decade in tech recruiting (at orgs like AppDynamics and Google) and am now a Director of Talent on Unusual Ventures’ founder support team (called GAP for “Get Ahead Platform”). In my role I work full-time for early-stage startups, sourcing world-class operators as companies scale. These hands-on experiences have given me a unique angle on the state of early-stage hiring, especially with the first sales leader role.

To bring these insights to the whole startup community I recently partnered with my colleague Dakota McKenzie, a Sales GTM leader with me on the GAP team. LIke me, he’s an operator (formerly on the sales teams at Segment and Databricks) who is now embedded full-time in early stage startups across our portfolio, doing the day-to-day work of building a great startup, informed by his repeat experiences as an operator. Dakota and other GTM members of our GAP team embed inside early-stage portfolio startups to prospect and build pipeline and manage teams. They then work with GAP Talent leaders like me to recruit hires and ultimately build a successful platform for a Sales VP to walk into on day 1.

Since we’re immersed in this work every day, we wanted to take a moment to collect our experiences together and share actionable tips and guidance for founders and sales leaders alike. So we recently led a live session on the specific tactics and guidance for matching sales leaders with early-stage startup roles.

An excerpt of that session is in this video below. But I also wanted to take a deeper dive on some of these topics here. Read on for collected wisdom from dozens of cycles hiring sales leaders, and recommendations for how to set-up the role for success.

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The most important things prospective sales leaders should understand about an organization before joining are:

Are they stage aware? People often romanticize building the sales function at an early-stage startup, but the truth is that it’s not an easy job. It’s a grind that requires a candidate to wear a dozen different hats while navigating a tough, pressure-packed journey. Make sure that you know what the role entails, and that you are ready to take on the responsibilities. 

Does the founder lead sales? The single most important thing a prospective sales leader should dig into, is how involved in the sales process a founder is. Can they show that they’re learning from customer conversations and evolving the sales process, and even the product, based on these discussions? Are they able to articulate the sales process (even if it’s not perfect) from end-to-end? Do they know how to close deals? Can, and will, they sit down with you and address important sales metrics? It’s extremely important to find a founder who understands why sales is important, and is empathetic to the challenges sales leaders face as they build an early-stage company’s revenue systems. 

Are they an evangelist or “coin-operated” leader? There are two types of CEO archetypes that sales leaders should look for: evangelists and “coin-operated.” Evangelists solve problems, dig deep to figure out what people want to buy. Coin-operated leaders are interested in what the company can sell right now and where the biggest deals are. Both are valuable, but at different stages of an organization’s lifecycle. Look for a visionary leader when joining a seed-stage startup – you’ll need a partner rather than someone to report into.

On the flip side of things, what do we advise founders to look for as they search for their first sales hire?

Can they set up a sales function to take the company from $1M to $15M ARR? Companies don’t necessarily need to look for someone who has had experience in the precise environment they’ll be walking into, but they do need to show that they’ve successfully built a revenue machine from the ground up before. Demonstrating the leadership capabilities necessary – both from a sales and people perspective – is essential.

Can they hire? Ultimately, the point of a sales leader is about both sales AND leading. The first step of that is scaling the org with a talented team. This requires great hiring skills, which are often related to great sales skills, but not always. Hiring is hard. Building an organization is hard. A candidate can be an ace salesperson, but if they don’t have good instincts on hiring the right people for the right roles, they’ll struggle as an early-stage startup scales.

I hope this deep-dive and our recorded session prove to be a helpful resource for anyone seeking an opportunity to build their own future at an early-stage startup. Be sure to check out the current openings across our portfolio, and new, actionable resources for early-stage startups in the Field Guide. Lastly, be sure to join the company-building newsletter of our Unusual Community for the latest resources and events!