Getting Your First Sales Hire Right

It’s one of the most important decisions you can make for your B2B bootstrapped startup. 

Most company founders wish they had done it differently. 

It’s an exciting time when you are a bootstrapped entrepreneur and your company has grown to a point where you need to hire your first salesperson. 

The natural inclination is to hire the person with the biggest list of contacts in your target market and let them loose on all those prospective clients. Too often, this approach fails. 

It’s probably not the salesperson’s fault, they had a solid track record and work ethic which is why you hired them in the first place. So, what gives? The reality is you hired someone that is not right for where you are as a business. 

Typically, experienced salespeople work in mature organizations that have all the support systems, marketing, and processes to help them close a sale. For a bootstrapped entrepreneur looking to make their first sales hire, all of those systems need to be developed, refined, and executed at the same time. That’s a completely different mindset and skillset than a typical corporate sales executive. 

Based on our extensive experience in the startup space, interviews with entrepreneurs, and qualitative research we have found a pattern for what constitutes the right mindset and skillsets for the first salesperson for a bootstrapped startup. These are the Pathfinders. 

What is a Pathfinder versus a “typical” salesperson? Clearly some of the qualifications overlap including understanding technology, positivity, communication skills and, obviously, the ability to close a sale. 

But areas where Pathfinders are different include:

• their ability to deal with ambiguity, as many startups and their products quickly evolve,
• not just a willingness but an excitement around building the processes and procedures necessary for a successful sales operation as an organization scales,
• they bring a curiosity that allows for creative solutions,
• their hunger is motivated by something quite different to most other sales types. 

These are all great, on paper. As a busy founder of a bootstrapped B2B organization, how do you go about finding a Pathfinder, which could be a needle in a haystack of resumes?  

The typical way startups go about hiring their first salesperson is to ask around and hire the most experienced person they can afford, often the person with the largest Rolodex. The challenge is, it doesn’t work that often. That has huge consequences in lost time, lost revenue and can even be an existential failure.  

Our team has been in your shoes. That’s why we’ve made The Right Five where we have focused on the unique requirements of the first sales hire of B2B tech founders. Through a proprietary sales recruitment technology, 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.  

What does The Five Right do? We automatically deliver B2B tech founders the right five Pathfinder salespeople to interview for their “first sales hire”, allowing them to get the right person hired quickly – which can make all the difference in the success or failure of a startup.