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The First Timer’s Guide To Being A VP Of Sales

I’m not afraid to admit this, but I’ve never done this before. I’m a first-time VP of Sales & Marketing. Anyone out there with me? I know I’m not alone. Jeremy Hitchcock is a first-time CEO. Tom Daly is a first-time CTO. Lisa Hagemann, our VP Engineering? No different. Cory, Josh, Gray, the three Chris’s, Alex, Neil, Erik, Brian… same boat. You get the point: the sink or swim, learn on the fly position is a common theme here.

The question we have to continuously ask ourselves: is this a strength or a weakness? Maybe it’s a cop out, but we put it in both categories in a SWOT analysis.

I recently had lunch with a business friend of mine Mark Roberge, the VP of Sales from DynECT Managed DNS client Hubspot. I always enjoy kicking around ideas with Mark as his approach is calculated and matured. Hubspot has MIT DNA in their blood and their success is staggering. Both Dyn and Hubspot aren’t exactly the same and Mark and I aren’t exactly the same, but that is not the point. Hubspot has 70 sales reps, an engaged and seasoned board and venture capital heavyweights in the mix.

But even Mark admits that he hasn’t done this before either.

We talk about everything from compensation strategies, lead generation efforts, customer retention, sales rep retention, performance plans, team-based vs. individual incentives, corporate structure, market segmentation, inside vs. outside and anything else that comes to mind. The topic hot in my world right now is Europe and Mark and I kick around his similar challenge for 2011. He’s never put feet on the ground abroad either.

Of course, there is context around every company, but the discussion points and measurables are the same. It’s fascinating to sit down with different contemporaries in similar roles and find out their not-so-unique challenges, what they’re paying attention to and most importantly, sanity check my own decisions.

Some have similar years of experience, some are gray haired and grizzled, but one thing remains consistent in every discussion — we’re trying to achieve the same exact things and face the same exact challenges.

As I strategize and plan out our impending UK office opening and search for British talent (I’m in London this week!), continue to grow our sales and biz dev team that was just three reps only nine months ago (we’re 16 today), build structure and focus within the team and obsess over revenue figures while making sure they don’t cut profitability, I find comfort in knowing that whether I had done this before or not, I’m not alone.


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Kyle York
Whois: Kyle York

Kyle York is GM & VP, Business & Product Strategy, and has been a long-time executive, having joined in 2008. Over the years, he has held go-to-market leadership roles in worldwide sales, marketing, and services. In his current role, Kyle focuses on overall corporate strategy, including: positioning and evangelism, new market entry, strategic alliances and partnerships, M&A, and business development. Outside of Oracle Dyn, Kyle is an angel investor, entrepreneur, and advisor in several startups.