Your first sales hire should be a missionary, not a mercenary
As the first sales hire at Cloudflare, I learned firsthand from both our high growth and my own mistakes how to build a world-class sales team. Early hires are the cultural cornerstones of an organization. As Vinod Khosla described the initial hires at Sun Microsystems, “Initial hiring is way more important than you think because of its multiplicative effect. So, it’s worth taking a little longer when you hire those people.”
The first sales hire will set the best practices, cultural tone and is responsible for making sure each subsequent new sales hire succeeds. For this reason, it is important that startups look to hire missionaries, not mercenaries, when they bring on their first sales team member. If the first sales hire is a “coin-operated” mercenary whose priority is to overachieve quota and is a great solo player, they may be more competitive than collaborative. In contrast, if the first hire is a missionary who cares more about evangelizing the product and is a team player, they will naturally enable the next set of hires to succeed.
Hiring the missionary
There is an overwhelming amount of declarative advice on how to make your first sales hire: They should have experience selling at an early-stage company, tenure in that company to a much larger team (five to 50 employees, or $100,000 to $10 million ARR), they’ve sold at your price point, overachieved quota consistently (beware of this one. Quota overachievement can be a false positive and may be the result of a fruitful territory, a comp plan where quotas were too low or selfish “me-first” behavior.), etc. What you should look for are missionaries, and they exhibit two key qualities: resourceful ingenuity and team-based behavior.
Missionaries are resourceful team players
At early-stage startups, there is more work to do than people to do it. These are resource-constrained environments where roles go beyond job descriptions and are “jack-of-all-trades” positions. This first sales hire is not an ordinary sales gig. It requires a missionary with a deep interest in the technology who wants to evangelize the product. The resourceful missionary must have an enterprising mindset to build their own sales collateral, a clever approach for testing pricing, a passion for the product technology and an ability to navigate the organization so engineering and product teams can hear the voice of the customer.
While resourceful skills are needed to test out different sales motions, the most important quality the missionary must have is a team-first attitude to share those learnings with colleagues. As the missionary, and the subsequent missionary hires, are developing a repeatable process they are engaging in novel intellectual work; this is not routine execution. When someone develops better messaging, or discovers a new use case, the goal is to spread that expertise so overall collective intelligence and team performance increases. If that operational know-how becomes siloed and an individual optimizes for themselves, instead of the team, the organization loses.