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Director of Enrollment, 2 Hour Learning (Remote) - $200,000/year USD

Crossover
Boston, MA Remote Full Time
POSTED ON 5/19/2026
AVAILABLE BEFORE 8/10/2026
Many enrollment positions focus on driving numbers. This position is designed to uphold quality.

Alpha is developing one of the most forward-thinking educational models globally. Our sites integrate demanding academic programs, technology-enhanced instruction, and elevated expectations for both learners and educators. Students routinely progress more quickly than national standards, supported by measurable evidence. The afternoon hours are dedicated to deeper exploration, independent work, and practical skill development. The model delivers results. Yet it succeeds only when matched with appropriate families.

This is your entry point.

You will manage the complete enrollment process for a campus, beginning with initial contact and concluding with onboarding. This position does not involve hand-offs. You are accountable for the family's experience, the clarity of their understanding regarding our approach, and ensuring enrollment choices are made with proper reasoning. You will evaluate compatibility, facilitate meaningful dialogue, and advise against enrollment when circumstances warrant it. The objective is not to maximize headcount. The objective is compatibility.

We welcome applicants from high-end service sectors outside conventional education: independent schools, selective initiatives, upscale hospitality, executive assistance, exclusive membership entities, or entrepreneurial operators who have directly overseen premium client experiences from start to finish. What counts is your capacity to execute a detailed, phased engagement with discernment, precision, and accountability.

If your professional background centers on delivering exceptional service in settings where confidence, care, and client experience shape reputation, this opportunity will resonate—simply directed toward work that generates meaningful impact.

This is a full-time, salaried, on-site position. We are recruiting in Greenwich, Boca Ratan, Palm Beach, Atlanta, Boston, Charlotte, Raleigh, and Chantilly. Relocation assistance is provided.

What You Will Be Doing

  • Taking full ownership of the enrollment experience for prospective families, spanning initial inquiry to completed onboarding.
  • Facilitating discovery conversations to evaluate alignment prior to proposing options or advising on subsequent actions.
  • Overseeing 20 concurrent family engagements across various enrollment phases, maintaining transparent tracking and timely follow-through.
  • Guiding campus visits, student shadow days, and enrollment discussions that articulate results, standards, and the intended audience for the model.
  • Ensuring precise CRM and enrollment documentation (HubSpot and SIS) to enable forecasting, prioritization, and consistent service delivery.

What You Won’t Be Doing

  • Employing volume-driven or aggressive conversion strategies.
  • Accepting families who do not align with the model merely to meet quotas.
  • Supervising sizable teams or navigating complex reporting hierarchies.
  • Distributing responsibility for family engagement across multiple personnel.
  • Operating remotely. This role is intentionally campus-centered.

Director Of Enrollment Key Responsibilities

Lead and deliver a trust-centered, selective enrollment process that attracts compatible families while safeguarding the quality and effectiveness of the Alpha educational model.

Basic Requirements

  • 3 years providing premium, individualized service in contexts where service excellence directly influences organizational reputation (education, upscale hospitality, executive assistance, exclusive membership, or independently operated services).
  • Proven ownership of a complete client, admissions, or enrollment process from initial engagement through final onboarding.
  • Experience managing 20 client, guest, or family interactions concurrently at varying stages, supported by an organized tracking and prioritization approach.
  • Capacity to share specific examples of advisory decision-making, including instances where you recommended against your offering when alignment was absent.
  • Professional written correspondence experience with senior leaders, affluent individuals, or discerning clients.
  • Willingness to reside in or relocate within 60 days to one of these locations: Greenwich, CT; Boca Ratan, FL; Palm Beach, FL; Atlanta, GA; Boston, MA; Charlotte, NC; Raleigh, NC; or Chantilly, VA.
  • Authorized to work in the United States without visa sponsorship.

Nice-to-have Requirements

  • Experience in admissions for selective independent schools or competitive enrollment programs.
  • Professional history in upscale hospitality, VIP client services, or executive support functions.
  • Experience developing or enhancing enrollment workflows, standard operating procedures, or service protocols.
  • Comfort leveraging data and CRM analytics to enhance enrollment alignment, not merely 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-Boston-DirectorofEnro1

Salary : $200,000

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