Creating the Playbook for Success

You’re a B2B tech founder. You’ve won some early deals proving that some people will pay for a solution to a problem you address. What now? How do you scale the knowledge and passion that you’ve inevitably brought to those early forays into the market?
The temptation (and well trodden approach) is to look to hire as ‘experienced’ a salesperson as you can afford in the hope they can break it big – someone with a track record with a ‘Name’ company in a related space. In the summer of 2020 I spoke to a founder who had bootstrapped her business and was on their seventh iteration of that first Sales hire. Unfortunately that outcome is all too common.
If we break down what a successful growth timeline looks like in B2B tech it’s easy to realise that the well trodden path is really a Hail Mary pass that skips the essential hire that is the Pathfinder salesperson.
This chart sets the growth timeline alongside valuation and investment stages but hiring a Pathfinder salesperson is just as essential to those B2B tech companies looking to continue to grow without external investment (i.e. to bootstrap).
The role of the Pathfinder is to develop a predictable, repeatable, scalable, profitable sales model. That means proving that non-founders can sell the proposition and that there are many customers willing to pay. It also means doing so within a framework of scalability and profitability. This requires testing to identify the correct target market; figuring out the route to that market (e.g. do partners have a role?); understanding how to create awareness in that market; turning that awareness into interest and leads and, finally, selling.
There’s a lot going on there before the final act of selling! Layer in the lack of support typically available in a startup; the ambiguity around knowing what to do first every day; the acumen to identify, and flexibility to pivot away from, dead ends; all of which has to be delivered with the discipline of documenting activity and associated metrics. All with an eye on spend because this is not a ‘spray and pray’ position.
Does this sound like your <Enter Big Name> Account Executive? Or an existing VP Sales managing a large team? Not unless you get extremely lucky and most don’t.
This is much more about teaching the company to fish than landing a [potentially unsuitable] whopper for them. Of course, deals still need to be done to generate revenue and prove the process works but, ultimately, the role of the Pathfinder salesperson (your first Sales hire) is to write the playbook that others can use to truly scale your business.
There is no cookie-cutter playbook that can be taken from elsewhere and dropped into your business. Your solution is different, your target market is different and the route to connect the two will be different.
We’ve described the role and required deliverables of a Pathfinder, but what are the characteristics that make a Pathfinder and how should you assess for those? Some of those characteristics we’ve mentioned in this post: the ability to deal with ambiguity; to identify a target market; a broad understanding of marketing that will facilitate the creation of awareness and the resultant generation of leads; sales skills etc. There are others, many of them, including the need to build something, curiosity, adaptability as well as the myriad vocational skills required to be a successful marketer, salesperson and partner strategist.
It’s a tall order but the good news is that The Right Five has codified all of these characteristics and developed an assessment that will identify Pathfinders as distinct from all other Sales types. All you have to do is include the assessment url as part of your job spec, sit back, get ready to interview the right five Pathfinders and then select one in the knowledge they can all do the job.
The Right Five to Get the Right One.