Why is making that first Sales hire so difficult?

One of the major challenges facing bootstrapped entrepreneurs is making that first Sales hire. This is evidenced by Mainsail Partner's annual survey of bootstrapped entrepreneurs:

Bootstrapped entrepreneur survey results

Despite, obviously, perceiving the Sales function as important to the future growth of the business, founders uniformly see it as a weakness. Interestingly, Marketing is seen as an even bigger weakness yet it's not seen as important - that's a story for another day but it is one that is inextricably tied up with the Sales function.

So why is Sales seen as important yet, at the same time, a liability? That's because founders hire the wrong type of Sales person as their first Sales hire. It can also be due to a founder's lack of skills in hiring Sales people and an urgency to work through a mountain of applications (without knowing the real criteria against which to judge those applicants).

So what is the 'right' type of Sales person that a founder should be looking for? To understand that we need to look at the growth stages of a typical bootstrapped company:

Startup Valuation Curve

This is a representational chart showing step-changes in startup valuation based on passing through certain growth stages. The chart speaks for itself in terms of those stages.

The transition from founder-led Sales to that first Sales hire is what's important here. The key requirement of that first Sales hire is to prove that: non-founders can sell the offering; that many people will pay; and that scale and profitability are achievable.

This requires the development of a predictable, repeatable, scalable and profitable Sales process. And that requires a totally different set of Sales skills to those required in a steady-state business where the Sales playbook is already defined. That requires someone who can teach you to fish - a Pathfinder Sales person.

When hiring for this first Sales role, many founders are swayed by the 'rolodex' Sales person who knows their sector, understands the client problem and who can simply pick up the phone and drum up interest from existing contacts. But what collateral can they use? Who will run a demo? How does this Sales process really work? How does 'rolodex' deal with ambiguity? Do they exhibit entitlement?

Hiring 'rolodex' when a Pathfinder Sales person is needed is the reason many bootstrapped entrepreneurs view Sales as a weakness, never grow beyond this stage (despite 6 or 7 attempts at hiring the 'right' Sales person) and, ultimately, it's a weakness that can prove to be an existential threat to the business.

We understand the skill set required of a Pathfinder Sales person. We run a full service recruitment agency, SearchPrizm, focused on hiring Pathfinder Sales people for B2B bootstrapped entrepreneurs. You can learn more at:


We're also in the process of developing our own SaaS product that will enable bootstrapped entrepreneurs to automate the hiring process for Pathfinder Sales people and which will include online testing for applicants against those Pathfinder Sales skills - ensuring that you get the 'right' Sales people into your business for the stage you're at.

To be kept informed on the release date for that product, please enter your e-mail address here: