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customers or revenue she generates, but from her ability to accelerate the
company toward product/market fit.”
The entrepreneur (candidate 3) is my most desirable candidate.
Here are the pros of the entrepreneur:
Entrepreneurial instinct. Of all the candidates on the table, the entrepreneur
is most likely to accelerate the company toward the right product/market fit.
In fact, this aspect of her role will probably be the element about which she
is most passionate. Given how important that piece is, her skills here are
tremendously valuable. She will dig in with prospective customers to learn
about their challenges, opportunities, perspectives, and priorities. She likely
has the entrepreneurial instinct to step back from these conversations and
help the CEO and the product team to identify the patterns and understand
where to pivot.
Sales fundamentals. I also love that she has received formal sales training
and gained experience at a large organization. These fundamentals should
enable her to engineer the appropriate sales methodology and structure it for
scale.
Leadership potential. Her entrepreneurial experience has likely equipped her
with the experience and ability to lead.
Here are the cons of the entrepreneur:
Sales management fundamentals. She has probably never hired or managed a
salesperson before. Despite this weakness, I would still bet on her ability to
get me through the product/market fit phase of the business. Once that's
established, I can monitor her reasonably closely as she begins to hire and
develop salespeople.
Industry knowledge. Like the sales manager, she does not have experience
with your target buyer and will need to scale the learning curve.
If you are in the process of thinking about your first sales hire, hopefully this
exercise helped to frame the decision.
To Recap my perspectives
When faced with the first sales hire decision, many founders put the