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Director of Enrollment Management, 2 Hour Learning - $200,000/year USD

Crossover
Boca Raton, FL Full Time
POSTED ON 6/9/2026
AVAILABLE BEFORE 8/31/2026
Most enrollment positions focus on maximizing numbers. This role is designed to uphold standards.

Alpha is developing one of the world's most ambitious educational models. Our campuses integrate demanding academics, technology-enabled learning, and elevated expectations for both students and faculty. Students routinely exceed national learning benchmarks, and the evidence supports this claim. Afternoon hours are dedicated to deeper exploration, independent work, and practical skill development. The model delivers results. But success depends entirely on selecting the right families.

This is your mandate.

You will oversee the complete enrollment process for a campus, beginning with initial inquiry and extending through onboarding. This is not a role where responsibilities transfer between departments. You are accountable for the family experience, for ensuring families fully comprehend our model, and for verifying that enrollment decisions are grounded in genuine alignment. You will evaluate compatibility, facilitate meaningful dialogue, and advise against enrollment when appropriate. The objective is not to maximize headcount. The objective is to achieve fit.

We welcome candidates from premium service sectors outside conventional education: selective independent schools, competitive programs, luxury hospitality, executive assistance, exclusive membership organizations, or entrepreneurial professionals who have directly managed sophisticated client relationships from start to finish. What counts is your capacity to execute a high-touch, multi-phase process with discernment, precision, and accountability.

If your career has centered on providing exceptional service where trust, confidentiality, and experience quality are the brand differentiators, this role will resonate—simply applied to work that produces measurable impact.

This is a full-time, salaried, on-campus position. We are hiring for Greenwich, Boca Raton, Atlanta, Charlotte, and Chantilly. Relocation assistance is provided.

What You Will Be Doing

  • Taking full ownership of the enrollment experience for prospective families, from initial outreach through final onboarding.
  • Facilitating assessment-focused conversations to evaluate fit prior to offering solutions or suggesting further engagement.
  • Overseeing 20 concurrent family engagements across multiple enrollment stages, maintaining transparent tracking and timely communication.
  • Delivering campus tours, student shadow visits, and enrollment discussions that articulate outcomes, standards, and the intended audience for the model.
  • Ensuring precise CRM and enrollment documentation (HubSpot and SIS) to enable accurate forecasting, appropriate prioritization, and consistent service delivery.

What You Won’t Be Doing

  • Deploying transactional or aggressive sales methods.
  • Accepting families who lack alignment simply to meet enrollment targets.
  • Overseeing a sizable team or working within complex approval hierarchies.
  • Distributing family experience responsibilities across multiple team members.
  • Operating remotely. This position is campus-based by intention.

Director Of Enrollment Management Key Responsibilities

Own and deliver a high-integrity, selective enrollment process that successfully converts aligned families while safeguarding the quality and effectiveness of the Alpha model.

Basic Requirements

  • 3 years providing premium, individualized service in settings where service excellence directly shapes brand perception (education, luxury hospitality, executive assistance, exclusive memberships, or independently operated services).
  • Proven ownership of a complete client, admissions, or enrollment process from initial contact through onboarding.
  • Experience managing 20 concurrent client, guest, or family relationships across varying stages, supported by a reliable tracking and prioritization system.
  • Capacity to offer specific examples of consultative judgment, including instances where you advised against your own product or service due to poor fit.
  • Professional written communication experience with senior leaders, high-net-worth clients, or discerning audiences.
  • Willingness to reside in or relocate within 60 days to one of these locations: Greenwich, CT; Boca Raton, FL; Atlanta, GA; Charlotte, NC; or Chantilly, VA.
  • Authorized to work in the United States without visa sponsorship.

Nice-to-have Requirements

  • Experience in competitive private school admissions or selective program enrollment.
  • Background in luxury hospitality, VIP client services, or executive support functions.
  • Experience designing or improving enrollment workflows, standard operating procedures, or service protocols.
  • Proficiency using data and CRM analytics to enhance conversion alignment, not simply conversion velocity.

About 2 Hour Learning

Education is broken, but 2 Hour Learning is proving it doesn’t have to be. They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.

With students consistently ranking in the top 1-2% nationally and the top 20% achieving an astonishing 6.5x growth, they’re proving that smarter learning is possible. At 2 Hour Learning, it’s talent and performance that matter.

They offer a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can be a part of fixing a broken school system.

2 Hour Learning is reprogramming learning for the AI era.

Here’s How They’re Fixing It.

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 $100 USD/hour, which equates to $200,000 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-5799-US-BocaRato-DirectorofEnro

Salary : $200,000

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