May 25, 2022

as a general partner At a classic Series A venture capital firm, I have the pleasure of talking regularly to the founders of cloud software companies. At this initial stage, there is still much to be done in building the business, including the development of professional salespeople.

Let me continue: the founders worked on this for almost two years, building the initial product and winning over the first group of customers; ARR is $200,000-$500,000. The first customers were brought in by the founders and the initial market was tested during this process. They recently hired the first BDR to bring in more leads.

Now the founders want to hire their first sales person and have a lot of questions. Hire a leader and build from the top down or start with a personal representative? What profile and experience should they have? Will it help them quickly hire a few sales reps?

Founders often come from successful cloud companies and have seen what an effective sales machine looks like during the development phase. But this is very different from a company that is just kicking off its sales engine, so my first conversation is usually about early and late sales.

Founders need someone who understands the big picture, understands the business, loves technology, and, most importantly, asks a lot of questions.

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Selling an initial product to an obscure group of customers in an emerging market is like being left in the woods with nothing but a knife. where’s the answer? Where is water, food and shelter? Who is friend or foe?

To be successful at this level, it takes a special salesperson—a highly intelligent, independent, inquisitive person who mentors potential customers. They need to be comfortable with the lack of clarity, resources, and direction.

Founders often proudly share the profile of a brilliant sales candidate who is the top performer and has been quoted in the multi-billion dollar cloud unicorn for three consecutive years. They are certainly influential, but probably not the right person.

Founders need someone who understands the big picture, understands the business, loves technology, and, most importantly, asks a lot of questions. They want an inquisitive salesperson who challenges, learns, and adapts to potential customers accordingly. This person also needs to be creative enough to imagine how technology can be useful in new and different ways.

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