Director of Enrollment, Founders School - $400,000/year USD at Crossover

You understand how to cultivate a relationship with a billionaire — and how to become the person they trust with their child's most pivotal decision. That defines this role. If your default instinct is to "manage applications" or "optimize a conversion funnel," you won't fit here. If your instinct is to take full ownership of a relationship for the long term, this could be the most rewarding position you'll ever hold.

Founders School is a four-year high school where students build genuine companies with the goal of $1M in profit before they graduate. Annual tuition is $150K, backed by a guarantee: $1M profit by graduation or full tuition refund. The program begins in New York City in Fall 2026 with 20 students and will scale to 1,000. Our families rank among the most accomplished and discerning on the planet — many hold wealth in the hundreds of millions to billions. Someone must own every one of those relationships: from initial contact through enrollment and well beyond.

This role resembles running investor relations at a premier fund — not admissions at a traditional private school. You steward a pipeline of high-net-worth prospects, lead them through a substantive decision-making process, secure their commitment to a significant investment, and then sustain the relationship for years so trust deepens over time: they re-enroll, enroll siblings, and bring in referrals.

What You Will Be Doing

• Taking full ownership of the pipeline of qualified prospective families — every lead, whether inbound, sourced at events, or referred, evolves into a genuine relationship centered on you. Consistent calls, thoughtful follow-through, and serving as the person who either knows the answer to any question or secures it immediately.
• Organizing events that connect prospective and enrolled families — ranging from large information sessions to smaller, curated dinners and gatherings.
• Shepherding families through application and diligence — articulating the school's model, the guarantee, and the student journey, and moving them from curiosity to enrollment without resorting to high-pressure tactics.
• Maintaining active engagement across the entire family ecosystem — those still deciding, those currently enrolled, and those whose younger siblings may follow. Proactive outreach ensures families hear from you before they need to reach out.
• Serving as the human embodiment of Founders School for these families, and establishing the scalable relationship-and-enrollment framework that enables the program to function and expand.
• Collaborating directly with school leadership who manage the highest-tier early conversations, while you construct the operational infrastructure beneath them.

Like a fund, the annual cycle has two phases: an active season focused on cultivating relationships with prospects and guiding them toward commitment, and a maintenance season dedicated to keeping enrolled families engaged, informed, and satisfied enough to renew their trust and recruit others.

What You Won’t Be Doing

• Selling. No commission structure, no enrollment quotas, and no aggressive closes. If a family ever feels pressured, the approach has failed. You are not a salesperson; you are their most trusted advisor in this decision.
• Managing selectivity. Traditional admissions revolves around rejecting 96% of applicants. We are building something unprecedented and persuading exceptional families to take a calculated risk on it.
• Handing families off after enrollment. The relationship does not conclude with a deposit — it marks the start of a multi-year engagement you continue to own.
• Getting buried in logistics. Scheduling, documentation, and administrative enrollment tasks are managed by operations. Your focus remains on families.

Director Of Enrollment Key Responsibilities

Within 6 months, you own the complete pipeline of prospective families in NYC — each one has an authentic relationship with you, and school leadership is no longer the constraint on any relationship below the highest tier. Families in the Fall 2027 cohort have been individually guided from interest through enrollment, every enrolled family receives proactive, scheduled outreach, and you have developed the initial messaging framework and relationship playbook that does not yet exist.

Within 12 months, the NYC enrollment pipeline operates as a repeatable system rather than an improvised effort — you can describe the pipeline status, conversion metrics, and health of every family relationship on demand. Enrolled families are renewing their trust and actively referring peers; retention and referrals are directly attributable to you.

As the program grows toward 1,000 students and expands to additional cities, you will recruit and lead the enrollment team — hiring talent, training them, and defining the family experience across all campuses. You are entering at the foundational stage of the function that will determine whether Founders School attracts and retains the right families.

Basic Requirements

• You are authentically comfortable and effective cultivating relationships with high-net-worth individuals. You have demonstrated this in a previous role — investor relations, private wealth management, private-client sales, luxury hospitality at the Four Seasons or Aman level, high-end real estate, or comparable contexts — and you can engage confidently with a billionaire, interpret their idiosyncrasies, and position yourself as a peer rather than a subordinate. This is non-negotiable.
• You are relationship-focused, not transaction-focused. You would be uncomfortable in a hard-sell, commission-driven environment, and you are motivated by building something enduring and excellent rather than maximizing a metric.
• You are sufficiently organized and self-directed to manage an entire pipeline independently. Nothing slips through the cracks, and no family ever feels neglected after committing.
• You are currently located in New York, NY, or prepared to relocate within 60 days.
• You are legally authorized to work in the United States.

Nice-to-have Requirements

• Investor-relations or relationship-management experience at a fund — the closest parallel to this role. This explicitly includes talented professionals who are exhausted by the fundraising cycle and seek to apply the same skill set to something more meaningful.
• An established network within, or credibility among, high-net-worth families in New York City.
• Authentic conviction in the mission — that entrepreneurship offers superior education compared to conventional paths — and enthusiasm for communicating that vision.

About Founders School

Founders School is a four-year high school built for ambitious students who want to create, build, and solve meaningful problems. The program combines Alpha School's elite academics, real-world experience, and mentorship from world-class entrepreneurs around three commitments to every student: Build a million-dollar business. Identify problems in the world worth solving. Master AI before adults do.

This is a place for people who'd rather build the thing than manage the thing. We're hiring the founding team that builds the dream high school for the most entrepreneurial and ambitious students in the country. Launching in NYC Fall 2026.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $200 USD/hour, which equates to $400,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5832-US-Paterson-DirectorofEnro