There’s some great content out there on the subject of hiring your first VP of sales at a startup, so in this post I’m going to do some quick thoughts on the subject in an effort to complement the existing corpus.
In other words, this is not your classic TLDR Kelloggian essay, but some quick tips.
- Hire them first. That is, before hiring any salesreps. The first VP of Sales should be your first salesrep. Hire someone who wants to walk (and even discover) the path before leading others. Hire someone who enjoys the fight.
- Hire them hopelessly early. Don’t wait for product availability. Don’t wait until you’ve hired 3-4 reps and they need a manager. Don’t wait until you have a bookings plan that needs hitting. Hire them as early as possible.
- Glue yourselves together for 6-12 months. You want to spend 6-12 months as Frick and Frack. Why? Most founders can sell their idea and their software. The real question is: can anyone else? By gluing yourselves together you will transfer a huge amount of critical knowledge to the sales VP. That, or you’ll drive each other crazy and discover you can’t work together. Either way, it’s good to succeed or fail fast. And the goal is total alignment. 
- Hire them before the VP of marketing. I know some very smart people who disagree with me on this question, but as a three-time enterprise software CMO (and two-time CEO) I take no shame in saying that marketing is a support function. We’re here to help. Hire us after hiring sales. Let the VP of Sales have a big vote in choosing who supports them .
- Hire someone who is a first-line manager today. Their title might be district manager or regional vice president, but you want someone close to the action, but who also is experienced in building and managing a team. Why? Because you want them to be successful as your first salesrep for 6-12 months and then build up a team that they can manage. In a perfect world, they’d have prior experience managing up to 10 reps, but even 4-6 will do . You want to avoid like the plague a big-company, second- or third-line manager who, while undoubtedly carrying a large number, likely spends more time in spreadsheets and internal reviews than in customer meetings.
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 Hat tip to Bhavin Shah for this idea.
 A wise VP of Marketing often won’t join before of the VP of Sales anyway.
 On the theory that someone’s forward potential is not limited to their prior experience. Someone who’s successfully managed 4-6 reps can likely manage 10-12 with one extra first-line manager. Managing 36 through a full layer of first-line managers is a different story. That’s not to say they can’t do it, but it is a different job. In any case, the thing to absolutely avoid is the RVP who can only manage through a layer of managers and views the sales trenches as a distant and potentially unpleasant memory.