Making that First Successful Sales Hire

path through the trees

I’ve yet to talk to anyone who disagrees with the statement that, for a B2B tech bootstrapped entrepreneur, making that first successful sales hire is extremely difficult. Heck, I’ve spoken to people who say they’re on to sales hire number 7 and have yet to find anyone who can “do the job”. In which case, those companies are lucky to exist after so many successive failures and survive only because of the continued sales efforts of the founder.

There is evidence of the challenge in the annual bootstrapped entrepreneur survey by Mainsail Partners.

MainSail Partners Importance Strength

This clearly demonstrates that the role of Sales is seen as being important while simultaneously being a weakness. Why is that case?

We’ve written previously about the ‘elephant in the room’ whereby neither the founder nor the new sales hire broaches the subject of lead generation at interview. The founder has hired the person with the best Rolodex (believing any lead gen function to be, therefore, unnecessary) and the Sales person who either believes there would be a lead gen function in place or doesn’t want to raise a potential ‘hole’ in their Rolodex during interview.

But, the issue is more fundamental than that. It’s not even [just] that the founder isn’t an expert on hiring, let alone an expert on hiring Sales people, it’s that the founder is hiring the wrong kind of Sales person for that first through the door role. With a likely mass of applications and limited time to sort through those applications the temptation, in the absence of a real understanding of what is required, is to look for the person with the most relevant experience, the one with the biggest Rolodex.

If ‘Rolodex’ guy or gal is ‘wrong’, why and what does ‘right’ look like?

To understand that, we need to look at the typical growth/valuation stages for a startup,

Startup Valuation Curve

Clearly, we’re talking here about the transition from founder-led sales to that first Sales hire around the time of seed investment (if needed). The role of that first Sales hire is to develop a predictable, scalable and profitable Sales process, which requires a ‘Pathfinder Sales’ person.

Further growth of the business together with institutional investment, based on a pre-developed sales process and an associated playbook, requires a different type of salesperson, a “Playbook Sales’ person.

The skill sets of the Pathfinder and Playbook Sales are totally different. As a simple example, the Pathfinder has little set in stone in terms of the Sales process. It needs developing, probably from scratch, possibly including target market definition. Doubtless is the fact that the level of ambiguity is extremely high. Contrast that with the Playbook person where the steps to success are defined – i.e. very little ambiguity.

Not shown on the chart is the likely domain of the ‘Rolodex’ Sales person. They’re probably working in a big tech company and have yet another set of skills **relevant to that role**. It may seem tempting to go hire someone with oodles of experience in Oracle’s healthcare sector team for your healthcare startup but that’s a sure path to failure.

There we have it. Different skill sets are required for the [totally] different requirements of the roles at each stage of the growth curve.

Our sister company, The Right Five, is the only sales recruitment technology focused on the unique requirements of the first sales hire of B2B tech founders – the Pathfinder salesperson. Years of start-up experience has enabled the definition of the role of the Pathfinder, the skill sets required to be successful in that role, together with the development of an online assessment tool that identifies Pathfinders as distinct from other, unsuitable, types of salesperson. The Right Five automates the assessment of all applications to deliver the right five Pathfinder candidates for interview such that the founder can select the right one.

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