You understand what it takes to cultivate a relationship with an individual whose net worth exceeds a billion dollars — and you know how to secure their confidence in a deeply personal, high-stakes decision affecting their child's future. That's what this role demands. If your default approach is to "manage applications" or "optimize conversion funnels," you won't succeed here. If, instead, you take full ownership of relationships and nurture them over years, this could be the most meaningful position you've held.
Founders School is a four-year secondary program in which students create genuine businesses targeting $1 million in profit by the time they graduate. Annual tuition stands at $150,000, backed by a guarantee: $1 million in profit by graduation, or full tuition reimbursement. The program begins in New York City in fall 2026 with a founding cohort of 20 students, with plans to expand toward 1,000. The families we serve rank among the world's most accomplished and selective — many hold net worths in the hundreds of millions or billions. Every single one of those relationships must be owned, from initial outreach through enrollment and well beyond.
This role resembles investor relations at an elite fund far more than it does traditional private school admissions. You'll steward a portfolio of high-net-worth prospects, guide them through a rigorous engagement process, shepherd them to commitment, and sustain the relationship over time so trust deepens and compounds — leading to re-enrollment, sibling enrollment, and active referrals.
Much like a fund, the calendar operates in two phases: an active cycle during which you cultivate relationships with prospective families and guide them toward commitment, and a stewardship cycle in which you keep enrolled families engaged, informed, and satisfied enough to renew trust and introduce others.
Within six months, you will own the complete pipeline of prospective families in New York City — each will have a personal relationship with you, and school leadership will no longer be constrained by relationship capacity below the highest tier. The fall 2027 cohort's families will have been personally guided from initial interest to enrollment, every enrolled family will be receiving proactive outreach on a defined cadence, and you will have authored the first iteration of the messaging framework and family relationship playbook that does not yet exist.
At the twelve-month mark, the New York City enrollment funnel will operate as a disciplined system rather than an ad hoc effort — you will be able to describe the pipeline, conversion metrics, and the health of every family relationship at any moment. Enrolled families will be renewing their commitment and actively referring others; retention and referral outcomes will be directly attributable to your stewardship.
As the program scales toward 1,000 students across multiple cities, you will recruit and lead the enrollment function beneath you — hiring, training, and defining the family experience at every campus. You are joining at the foundational stage of the function that will determine whether Founders School attracts and retains the right families.
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 hard to qualify – on purpose. High standards mean every educator, leader and EdTech builder is at the top of their game.
Top performers earn what they’re worth. Six-figure education roles aren’t fantasy here – they’re the baseline for excellence.
Skills carry more weight that resumes here. Demonstrate learning mastery, AI fluency and passion for what’s next. That’s what counts.