Diligent vs BoardPro for Coaching Academies' Equity Grants

Coaching and cohort businesses scale by handing responsibility, and often ownership, to the instructors who actually run cohorts. A founder brings on a lead instructor for a new track, offers a small equity stake to keep them past the first year, and the conversation happens over a call rather than in a board packet. Multiply that across several tracks and a couple of years, and the informal promises outnumber the documented ones. None of this is malicious; it is simply how a service business staffed by teaching talent tends to grow, and it leaves a gap between what people believe they own and what a resolution actually says.

A defensible grant needs four things on file: the board resolution approving it, the vesting schedule, the instructor's signed acknowledgment, and a cap table entry that matches all three. Missing any one of those turns a handshake into a dispute the moment real money is on the table, whether that is an acquisition offer or a falling-out with the instructor who was promised the stake. The tool matters less than the discipline, but the tool should make it hard to skip a step, not easy.

A single-entity academy with three or four directors and infrequent equity events can run this discipline on BoardPro: a resolution template for grants, a place to attach the vesting schedule, and a record a founder can point to when an instructor asks what they actually own. It is inexpensive to set up and easy for a non-lawyer to operate correctly, which matters more than any feature list when the person running the board record is the founder, not a corporate secretary.

Once outside investors join the cap table, once grants start including performance vesting tied to enrollment or retention targets, or once the academy operates through more than one entity for tax or franchise reasons, the record needs Diligent's tighter audit trail and permissioning. Investors and their counsel will eventually ask for the full grant history during diligence, and a gap in that history is treated as a real risk, not an administrative slip. The heavier system earns its complexity exactly at the point a stranger will read the file.

Before the next cohort launch, list every verbal equity promise anyone on the founding team remembers making, going back to the first instructor hire. For each one, write the share count or percentage as everyone remembers it, the vesting terms if any were discussed, and whether the instructor is still with the academy. Take that list to counsel, convert the ones that should be honored into real resolutions with signatures, and formally decline the rest in writing. The list will be shorter and less comfortable than expected, and that is exactly why it needs to exist on paper.

Work through the cleanup in this order:

1. List every verbal equity promise anyone on the founding team remembers making, going back to the first instructor hire.
2. For each promise, write down the share count or percentage as people remember it, plus any vesting terms that were discussed.
3. Note whether each instructor is still with the academy, since that changes what is fair and what is urgent.
4. Take the list to counsel and convert the promises worth honoring into documented grants with a resolution and a signed acknowledgment.

Unvested equity is where most academies discover their documentation was never adequate in the first place. An instructor who leaves after a year and a half, with a promised grant that was never formally papered, will often still believe they are owed something close to what they were told verbally, regardless of what a vesting schedule would have said had one existed. A clean resolution avoids this by stating the vesting schedule and any clawback terms plainly at the time of the grant, not after a departure becomes contentious. Academies that skip this step end up negotiating exits based on memory and goodwill instead of a document, which rarely goes well for either side.

A typical employee option pool assumes a single, standardized vesting schedule administered by HR or finance. Instructor equity at a coaching or cohort business is usually more bespoke: different instructors negotiate different terms depending on the track they run, how much of the curriculum they built, and how replaceable they are. That variability is exactly why informal handling breaks down faster here than at a typical startup. Each grant needs its own resolution rather than a single boilerplate template, and the board record needs to hold all of them individually, searchable by instructor, so nobody has to reconstruct which terms applied to which person years later.