Many startups come to the point when they need to hire a big hitting sales person to scale revenues to the next level. Deal sizes are getting bigger, contacts at customers are getting more senior, but sales are not growing as fast as they should. This is a common pattern and the most obvious response (and often the right response) is to hire an experienced sales person to take the business to the next level.
The first thing to say is be careful. There are a lot of sales people who turn out to be better at selling themselves to startups than they are at selling product. They will join your company on a high salary, insist on a quarter or two of guaranteed commission and delay you by up to twelve months.
That said, there are some killer sales people out there who can really make a difference. If you do find one of those, then hire them, but heed the following advice, which is from a guest post by Phil Sugar on AVC:
[As CEO] I go on as many sales calls and customer visits as I can. I’ve been told that once I hire a Head of Sales, I should stay out of the process. I totally disagree. I am not going to be the one managing the process, but I want to hear what the market is saying directly. A salesperson can’t be objectively assess the market, they are too close, their livelihood depends on the sale, same for the VP. They have to be optimistic, they have to try and make the fit whether it’s pushing the company to do something or pushing the customer to accept something. The best information you are getting from them on your market is second-hand hearsay. I’ve sat on boards and watched as projections get trashed as sales get pushed from one quarter to the next and the CEO sits by helplessly, not knowing why as they weren’t on the calls. I am not going to be that guy.
On half a dozen occasions now I’ve seen a new Head of Sales come in and push everyone else out of the sales process. All of those situations ended badly. Worse, when only sales have a line to the customer and the deals aren’t closing you have an interested party controlling information and it is often hard to know whether the culprit is sales execution, the product, or the market.