The Challenge of Bootstrapped Sales

Steve LudwigPathfinder SalesLeave a Comment

finding a path through the woods

It’s a common problem, yet it seems one that has yet to be solved—getting the first sales hire right in a B2B bootstrapped startup.  

In the years we have worked in the startup space, the entrepreneurs that we have interviewed, and from all the literature bemoaning the subject, Sales continues to be a huge priority and a huge miss. 

Mainsail Partners annual survey of bootstrapped entrepreneurs showed that Sales is viewed as the most important function yet is seen as the second greatest weakness behind Marketing.

chart showing how bootstrapped entrepreneurs view sales as their most important business issue

Source: Mainsail Partners

We’ve spoken to people who say they’re on to sales hire number seven and they have yet to find anyone that can “do the job” properly. 

If you think about it, those companies are lucky to exist after so many successive failures and survive only because of the continued sales efforts of the founder. While we applaud the talents of the founder, it is no way to scale a business and thrive.  

As we discussed in our post Getting Your First Sales Hire Right, a major challenge is hiring a Pathfinder salesperson. That individual has the right mindset and skills to thrive as the first in Sales at a bootstrapped startup. 

Many salespeople that come from established environments are used to a built infrastructure (marketing, sales support, systems, existing reputation, etc.) that supports lead generation, landing sales appointments, or at least making meeting with qualified prospects less challenging.

Not so for the first sales hire in a bootstrapped startup. They are starting from scratch. 

It’s not even [just] that the founder isn’t an expert on hiring, let alone an expert on hiring Salespeople, it’s that the founder is hiring the wrong kind of salesperson 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, often the one with the biggest Rolodex.

If these other Sales types are 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

We are talking 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 salesperson.”

Pathfinders have a very distinct and unique skillset. The have an ability to work with the ambiguity that occurs in startups that change and adapt as they grow; have an excitement around building something new; is a curious problem solver; and remains positive no matter what comes their way.  

Other Sales types (playbook and strategic sales, for example) are incredibly valuable in the right setting, but are the wrong fit at this stage of company development. They’re probably coming from a big tech company and have a set of skills that are really important in their current role, but those skills don’t translate to what bootstrapped B2B entrepreneurs need. 

Okay, that’s all well in good. But, with the flood of resumes an exciting startup sales job will attract, how do you find the Pathfinders? The Right Five. 

Through our personal experience combined with qualitative and quantitative research, we have created a proprietary sales recruitment technology process to make hiring that first salesperson for your B2B startup a success. The Right Five automates the assessment of candidates and brings you five of the right type of candidates—Pathfinders—so you can choose the right one.  

The Five Right takes the guesswork out of hiring that first sales role, so you can get it right the first time. We all know that having a successful first sales hire can make all the difference in meeting your business and growth goals.

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