Your entry into private school leadership was driven by a desire to influence how children are educated—not to manage fundraising efforts or mediate parent committees. A version of this role exists where the academic framework is safeguarded centrally, operational functions are handled by dedicated teams, and your time is devoted to what you do exceptionally well: engaging the families who have the greatest impact, converting them into champions, and serving as the definitive voice when difficult conversations arise.
You will lead the parent-facing side of Alpha in a single metropolitan area—Miami, San Francisco, or Los Angeles. Success will be measured by enrollment and advocacy: prospective ultra-high-net-worth families who commit, current UHNW families who re-enroll, refer others, and publicly endorse 2 Hour Learning, and a regional community in which Alpha maintains strong visibility. Approximately half your time will be externally focused—cultivating community partnerships, conducting information sessions, and holding one-on-one discussions with discerning parents who have engaged with every AI critique and expect to understand why this model delivers.
The remainder of your role serves as the escalation point. When an Associate Dean of Parents encounters a situation beyond their authority—a prominent family considering withdrawal, or a campus beginning to dilute the model to appease a vocal parent—you step in. You preserve both the family relationship and the integrity of the model. Then you create a documented precedent so the Associate Dean network can address similar issues independently in the future.
If you have led a private or independent K-12 institution, or you have built a career earning the confidence of UHNW families in a different sector, and you have been seeking a position where sound judgment and persuasive communication are the core outputs, this is that role.
Establish a metropolitan region where Alpha families serve as 2 Hour Learning's most vocal supporters—and where no parent challenge is addressed by diluting 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.