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Promoting Myself to Head of Sales

When I was in business school (way back in 1997), everyone wanted to be a product manager. It’s challenging. You sit between the engineering and sales departments and get to run a little P&L inside a big company. But my undergrad degree is in Buddhist and Western Psychology and I wanted to work in tech companies. No smart tech company would hire a psych major as a product manager. So after my MBA I joined a small company as VP of Sales.

Although the details are different, many salespeople find themselves stumbling into the role. Few of us wake up one day and think “I want to sell stuff for the rest of my life.” Many of us end up in sales because we don’t really fit in other roles. Then we discover that working in sales is actually exciting. You have an incredible opportunity to impact your organization. You are at the pointed end of the spear. You hear directly from customers about what they love – and don’t love – about your company. And, best of all, it’s different every day.

When we closed our seed round at Yesware, one of the bits of advice that Brad Feld of Foundry Group and Rich Miner of Google Ventures gave to me was: “Don’t sell the Yesware product.” This was bizarre to me. I sell stuff… that’s what I do! And now two of the smartest people in early-stage investing were telling me not to sell? Baffling.

Their point was that we needed to focus like crazy on the product first. We had the start of a great engineering team in our cofounder and CTO Cashman Andrus. But we also needed a product owner, an internal customer, to guide priorities and incorporate customer feedback. Being a salesperson, I was the perfect candidate. Being the other full time cofounder, I was also the only candidate. Finally, I got my chance to be a product manager!

Joe Kraus, cofounder of Excite and partner at Google Ventures, has a post today called “First Fire Thyself,” encouraging CEOs to move out of skill positions sooner than they probably feel comfortable in order to free up time to look ahead.

I completely agree with the sentiment, although I’m not a huge fan of that word, so I’d prefer to say that I’m giving myself a promotion. Now that Jake Levirne has joined Yesware as VP of Product, I’m promoting myself up to head of sales.

It was great to be a product manager. I loved almost every minute of it and I learned a lot. Perhaps the most important lesson is that I’m a salesperson at heart. And I’m thrilled to be going back into the thick of the battle.

P.S. Thanks to good friend Chris Johnson for the blog post suggestion. I hope it comes close to meeting your very high standards!