I think unless the other person proposes himself / herself the key is to set up a strong structure for the pilot. Things like how long, milestones, how they will make the decision to scale. My consistent experience in the health and car industries is to have this conversation earlier than later.
Thanks Nick! I don’t have as much experience in edtech but I’d think you want to maximize leverage ie get quickly to decision-makers that influence other decision-makers. I am thinking people like (i) someone overseeing an entire district, or (ii) the key person for a school system with various branches, or (iii) government bodies that can get you a mandate.
Good point Chris Beckmann, there is a bias here on Internet startups which tend to be highly efficient per employee. But another big confounding factor is funding. A team of 10 often pulls of a series A and the next decile of employees would be exposed to a different risk-reward curve.