Director of Enrollment
$400,000 USD/year Pay is set based on global value, not the local market. Most roles = hourly rate x 40 hrs x 50 weeks 

New York, NY, US
In-person
full-time (40 hrs/week)
Flexible schedule
Long-term role

Director of Enrollment   $400,000 USD/year

Description

You understand how to cultivate a relationship with an individual worth a billion dollars—and how to become their trusted partner for the most consequential decision they'll make on behalf of their child. That defines this role. If your default approach is to "manage applications" or "optimize conversion," this position is not for you. If your instinct is to assume complete ownership of a relationship, sustained over years, this may be the most meaningful role of your career.

Founders School is a four-year high school where teenagers launch real businesses targeting $1M in profit by the time they graduate. Annual tuition is $150K, with a guarantee: $1M in profit by graduation, or full tuition refunded. The program begins in New York City in Fall 2026 with 20 students and scales toward 1,000. Our families rank among the world's most accomplished and discerning—many hold net worths ranging from hundreds of millions to billions. One person must own every one of those relationships, from initial contact through enrollment and well beyond.

This position resembles investor relations at a premier fund far more than traditional admissions at a private school. You steward a pipeline of high-net-worth prospects, guide them through a rigorous process, secure their commitment to a major decision, and then sustain the relationship for years so trust deepens: they re-enroll, enroll siblings, and refer others in their network.

What you will be doing

  • Managing the complete pipeline of qualified prospective families—every lead, whether inbound, sourced at an event, or referred, becomes a substantive relationship with you at its center. Regular touchpoints, attentive follow-through, and serving as the person who either answers any question immediately or secures the answer promptly.
  • Organizing events that convene prospective and enrolled families, ranging from larger informational sessions to more intimate dinners and gatherings.
  • Leading families through the application and diligence journey—articulating the school's model, the guarantee, and the trajectory, and moving them from curiosity to enrollment without resorting to high-pressure tactics.
  • Maintaining engagement across the entire family ecosystem—those considering, those enrolled, and those whose siblings will 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 constructing the repeatable relationship and enrollment system that enables the program to operate and scale.
  • Collaborating directly with school leadership who manage the highest-tier conversations early on, while you establish the operational infrastructure beneath.

Similar to a fund, the calendar follows two phases: an active season focused on building relationships with prospective families and guiding them toward commitment, and a maintenance phase devoted to keeping enrolled families engaged, informed, and satisfied enough to renew their trust and introduce others.

What you will NOT be doing

  • Engaging in sales tactics. There is no commission structure, no quota, and no aggressive closing. If a family experiences pressure at any point, we have failed. You are not a salesperson; you are the person they trust most throughout this decision.
  • Administering selectivity. Traditional admissions revolves around rejection at institutions with 4% acceptance rates. We are constructing something new and persuading exceptional families to invest in it.
  • Transferring families to others and stepping away. The relationship does not conclude with the deposit—it marks the start of a multi-year partnership you continue to own.
  • Becoming overwhelmed by administrative tasks. Scheduling, documentation, and enrollment logistics are managed by operations. Your focus remains entirely on families.

Key responsibilities

Within 6 months, you assume ownership of the full pipeline of prospective NYC families—each has an established relationship with you, and the heads of school are no longer the constraint on any relationship outside the top tier. Families in the Fall 2027 cohort have been personally shepherded from interest to enrollment, every enrolled family receives proactive touchpoints on a defined cadence, and you have developed the initial messaging framework and family-relationship playbook that does not currently exist.

At the 12-month mark, the NYC pipeline operates as a reliable system rather than an improvised effort—you can describe the pipeline status, conversion metrics, and the health of every family relationship at any moment. Enrolled families are renewing their commitment and generating referrals; retention and referral outcomes are directly attributable to your work.

As the program expands toward 1,000 students across multiple cities, you recruit and lead the enrollment team supporting 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 enrolls the right families.

Candidate requirements

  • You are authentically comfortable and effective cultivating relationships with high-net-worth individuals. You have done this in a previous capacity—investor relations, private wealth management, private-client sales, luxury hospitality at the Four Seasons / Aman level, high-end real estate, or comparable—and you can engage confidently with someone worth a billion dollars, interpret their individual preferences, and function as a peer rather than a subordinate. This is essential.
  • You are relationship-oriented, not transaction-oriented. You would feel uncomfortable in a high-pressure, commission-driven environment, and you are motivated by creating something enduring and exceptional rather than merely hitting targets.
  • You possess the organization and initiative to manage a pipeline independently. Nothing is overlooked, and no family ever feels neglected after committing.
  • You are based in or willing to relocate to New York, NY within 60 days.
  • You are legally authorized to work in the United States.

Nice to have

  • Experience in investor relations or relationship management at a fund—the closest parallel to this role. This explicitly includes talented individuals who are exhausted by the fundraising cycle and wish to apply the same skill set to something with greater purpose.
  • An established network or credibility among NYC high-net-worth families.
  • Authentic conviction in the mission—that entrepreneurship offers a superior education to the conventional path—and enthusiasm for conveying that narrative.

Meet a successful candidate

Watch Interview
Chris Hayes
Chris  |  L2 Guide
United States

Ever wondered if work is enhancing your life, or erasing it? After years of late nights as a fitness coach left him exhausted and disconnect...

Meet Chris

Applying for a role? Here’s what to expect.

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.

Chat-style
screening interview.
STEP 1

Chat-style
screening interview.

Cognitive 
aptitude test.
STEP 2

Cognitive 
aptitude test.

Prove real-world 
job skills.
STEP 3

Prove real-world 
job skills.

Interview with the hiring manager.
STEP 4

Interview with the hiring manager.

Pass
proctored test.
STEP 5

Pass
proctored test.

Accept job offer.
STEP 6

Accept job offer.

Frequently asked questions

About Crossover

Meet some people who've landed similar jobs

Why Crossover

Recruitment sucks. So we’re fixing it.

The Olympics of work

The Olympics of work

It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.

Premium pay for premium talent

Premium pay for premium talent

Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.

Shortlist by skills, not bias

Shortlist by skills, not bias

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.

Crossover Logo White
Follow us on
Have a question?

Get answers to common questions using our smart chatbot Crosby.

HELP AND FAQs

Join the world's largest community of  AI first Remote WorkersAI-first remote workers.