How to Hire a Startup Head of Sales – Lessons From Scaling 500+ Sales Teams

Finding the right leader to scale your sales engine is one of the most important decisions a startup executive makes. If you find the wrong person, it can be a “game over mistake” – you’re out $500K in salary and search, you bring on the wrong sales reps, and start moving in the wrong direction.

At Almanac we’re building a collaborative editor that helps teams keep organized so they can focus on the work itself. We partnered with CloserIQ to publish their workflow on how to hire a head of sales.

We recently sat down with their founder Jordan Wan to share his step-by-step process for hiring the right sales talent in person.

6 Steps to Hiring the Right Head of Sales

Here’s Jordan’s basic process, including links to templates you can copy and use in your own team:

8 Mistakes to Avoid When Hiring a Head of Sales

Finally, keep in mind these eight anti-patterns when hiring a head of sales:

    1. Overvaluing big company experience. It’s easy to proxy fit with impressive big company brands and achievements. But a sales leader from will likely have trouble at an early stage with no brand and no budget.
    2. Leadership misalignment. If co-founders express dramatically different expectations in the sales needs self-assessment, pause the hiring process. Discuss.
    3. Skipping gap analysis. Without a gap analysis of your sales engine, you’re shooting in the dark.
    4. Hiring a VP too early. Hiring a systems-builder before a few good AEs can sell reliably is often disastrous.
    5. Thinking too long-term. Focus on the next 12-18 months. You can always add an executive down the road.
    6. Founders not doing initial screening for head of sales. Founders need to screen head of sales candidates themselves.
    7. Hiring generalist firms. You wouldn’t go to a generic doctor for a specialized surgery, so why do that when it comes to finding your head of sales?
    8. Fixating on title. Until you’re far up the sales learning curve (and sales manager leveling chart), don’t worry about title; just call it “head of sales.”

Taylor Thompson

Taylor Thompson is the Co-founder of Almanac, a collaborative document editor. Taylor led partnerships for literacy tech nonprofit Curious Learning, worked at Clay Christensen’s think tank and co-founded PharmaSecure. Taylor is an Echoing Green fellow, an contributor, and holds an A.B. from Dartmouth College and an MBA from Harvard Business School.