As general partner in a classic Series A venture capital firm, I have the pleasure of regularly speaking to cloud software company founders. At this early stage, a lot of company building has yet to be done, which includes the development of a professional sales team.

Let me set the scene: The founders have been at it for about two years, built an early product and won their first cohort of customers; ARR is $200,000-$500,000. The early customers were roped in by the founders, and the initial market was validated in the process. They just recently hired a first BDR to generate more leads.

Now, the founders want to hire their first sales professional and have a lot of questions. Hire a leader and build top-down, or start with an individual rep? Which kind of profile and how much experience should they have? Will hiring a few reps right away help them grow faster?

Founders often come from successful cloud companies and have seen what an efficient sales machine looks like at the growth stage. But that is very different from a company just starting its sales engine, so the first discussion I usually have is about early versus later-stage sales.

Founders need someone who gets the big picture, understands the business domain, loves the technology, and, crucially, asks a lot of questions.

Mind the stage

Selling an early product in a nascent market to an unclear set of customers is like being dropped into a jungle with nothing but a knife. Where is north? Where is water, food and shelter? Who is friend or foe?

It takes a special type of sales professional to be successful at this stage — a highly intelligent, self-directed, curious person who is consultative with prospects. They must be comfortable with a lack of clarity, resources and direction.

Founders often proudly share the profile of a hot-shot sales candidate who is a top performer and exceeded quota three years running at a billion-dollar cloud unicorn. They are certainly impressive, but likely not the right person.

Founders need someone who gets the big picture, understands the business domain, loves the technology, and, crucially, asks a lot of questions. They need a salesperson with an inquisitive mind who appropriately challenges the prospects, and learns and adapts quickly. This person should also be creative enough to envision how the technology can deliver value in new and different ways.



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