I did a lot of due diligence before going to DocuSign, but I was not given access to a variety of sales people to ask about deal size. In the interview process they gave me 2 "poster children" who'd earned a ton of money in sales. But like kings and peasants, a small few were making any money and EVERYONE else starved. When I first arrived I was shocked by how little my installed customers were paying us. I was concerned about hitting quota, let alone surpassing it. It was important to me that I surpass quota b/c the DocuSign comp plan (OTE) is below market. For the first 6 months I kept wondering how we sold bigger deals. But they were all very small and tactical. I set out to ask a smattering of other Account Executives how they were doing, and the 10 other people I spoke to that had been there for a while confirmed my fears. While some did indeed close a large deal for the year, it still barely put them at quota and the OTE was sub-market. People who had been there for 3 years were still not doing well compared to how they had done in the past. I gave it my best effort to see if I could overcome the small deal size by increasing volume. And although the deal volume was there I was working on transactions that were smaller than I did in my twenties. I don't recommend this job to anyone in Enterprise sales who is looking to sustain their earnings track record. There is a new SVP of Sales who knows what he's doing, however, I would give it a full year of him fixing things before even entertaining a sales job there. I'd be concerned that if he was not successful he may not stay either. The root of the problem is the DocuSign although the best product in this class, is a point solution that is not considered to solve a broad series of business processes, and it's just hard to yield the kind of deal size that true enterprise applications can.
