You entered private school leadership to influence how students develop, not to manage fundraising drives or mediate parent governance structures. A version of this role exists where the educational framework is safeguarded on your behalf, operational functions are centrally managed, and your time is devoted to what you do best: securing the confidence of the most influential families, transforming them into champions, and serving as the definitive voice when discussions become difficult.
You will lead the parent dimension of Alpha within a single metropolitan area — Miami, San Francisco, or Los Angeles. Success is measured by enrollment and advocacy: prospective ultra-high-net-worth families who commit, existing UHNW families who remain, refer others, and publicly endorse 2 Hour Learning, and a regional presence where Alpha is consistently top of mind. Approximately half your time will be externally focused — forging community alliances, leading information sessions, and engaging in one-on-one dialogue with discerning parents who have studied every AI critique and want to understand why this model delivers results.
The other half of this position serves as the escalation channel. When an Associate Dean of Parents encounters a situation beyond their resolution capacity — a prominent family threatening withdrawal, a campus subtly diluting the model to appease a persistent parent — it escalates to you. You preserve both the family relationship and the integrity of the model. Then you codify the resolution so the Associate Dean network can manage similar cases independently going forward.
If you have led a private or independent K-12 institution, or you have built a career earning the confidence of UHNW families in another sector, and you have been seeking the position where sound judgment and persuasive communication are the core outputs, this is that role.
Develop a metropolitan area where Alpha families serve as 2 Hour Learning's most vocal advocates — and where every parent challenge is resolved without compromising the integrity of the model.
Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.






It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.
Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.
We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.