The Right Five Journey (part 1)

We thought it would be fun/useful/interesting to create a blog series that tracks our journey.
This is different to the usual ‘how they were successful’ story in that it’s a real time account (this first post excepted) of what we’re up to, our strategies and tactics, our successes and failures, warts and all. This first post is a brief catch up. We’ll keep it brief because it’s in the past, subject to our own storytelling bias and subsequently neither real-time nor interesting.
It all started with Mainsail Partner’s annual bootstrapped survey which highlighted the fact that Sales was seen as a critical factor for success for bootstrapped companies while, at the same time, being viewed as a major weakness.

Source: Mainsail Partners
Myself and Rob were discussing this and figured out that the root cause of this dichotomy was the founder’s inability to get that first Sales hire right which in turn was based on their not understanding what was required of the role and consequently the person hired.
This was further compounded by the usual mountain of applications for these early stage roles with the potential for significant exits. Our personal experience was of founders shortcutting the resumé haystack in ways that were detrimental to any chance of finding the right candidate.
We came up with the basic idea for The Right Five – automating the process of selecting the right five candidates from the resumé haystack such that the founder just had to pick one – but our initial ‘assessment’ model for the right five was flawed. We thought we could use core values as the major assessment model. Wrong.
Around this time, Rob went out for a bike ride and din’t come back for a very long time thanks to a car and a lamp post that didn’t do the decent thing and bend when he hit it. He’s OK now and in his absence I discussed the idea with another good friend, Steve. Steve liked the idea and introduced me to his friend, Kurt who had the background we were missing in being able to develop an assessment for core value matching.
After a period of discussing the opportunity, we agreed to go out and research the basic tenets of the business properly. This was a smart move as, in doing so, we moved away from core values as the basis for assessment and developed the model we are now bringing to market. A recognition that the first Sales hire for a bootstrapped entrepreneur should be a Pathfinder salesperson whose role is to develop the playbook for future salespeople; together with the skills required to fulfil the role of Pathfinder salesperson.
Given that complete definition of a Pathfinder and their role, we were then able to develop an assessment to test candidates for suitability for the role. In Summer 2021, we tested the assessment using Survey Monkey against a cohort of known Sales types – some we expected to be Pathfinders, the rest we expected not to pass through our Pathfinder filter. It worked beautifully.
None of our co-founders are developers. We briefly looked around to see if we could identify a fifth co-founder with software development skills but that’s a tight market and [you’ll love this] we didn’t know what we were really looking for and couldn’t identify it (or assess for it) if it was stood in front of us. Rather smartly we went on a journey of identifying a white label partner or a company who could develop our software product for us.
Largely down to IP ownership we decided on outsourcing the development of the product to a dev shop in the Ukraine. Funded by the four co-founders, the dev project started on Dec 13 and our target completion date is the end of February. That’s us up to date.
In future posts in this series, we’ll add colour to our dev project, talk through our go to market plans (including target market identification), talk pricing, business model considerations, opportunities to expand our business beyond the initial target market – all through a real-time lens. It’ll be fun, these things always are. Merry Christmas y’all.