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

Crossover
Boston, MA Remote Full Time
POSTED ON 5/28/2026
AVAILABLE BEFORE 8/10/2026
Most enrollment functions are designed around volume. This one is designed around standards.

Alpha is constructing one of the world's most rigorous school models. Our campuses integrate demanding academics, technology-enabled learning, and elevated expectations for both students and staff. Students routinely outpace national learning benchmarks, supported by measurable outcomes. Afternoons are reserved for depth, independence, and the development of practical skills. The model delivers results. But it depends entirely on enrolling the right families.

This is your remit.

You will manage the complete enrollment experience for a campus, from initial inquiry to onboarding. This is not a role where responsibility is distributed. You are accountable for the family's perception of Alpha, the clarity with which they grasp the model, and whether their enrollment decision reflects genuine alignment. You will evaluate fit, facilitate informed discussions, and advise against enrollment when appropriate. The objective is not to maximize numbers. The objective is to ensure alignment.

We welcome candidates from premium service sectors outside traditional education: selective private schools, competitive programs, high-end hospitality, executive assistance, exclusive membership organizations, or owner-operators who have independently managed high-stakes client relationships from start to finish. What counts is your capacity to execute a sophisticated, multi-phase process with sound judgment, precision, and accountability.

If your career has centered on delivering exceptional service where trust, discretion, and experiential quality are brand-defining, this role will resonate—only here, it's applied to work that meaningfully shifts outcomes.

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

What You Will Be Doing

  • Directing the complete enrollment experience for prospective families, beginning with initial contact and concluding with onboarding.
  • Facilitating needs-based conversations to evaluate alignment before offering solutions or advising on next actions.
  • Overseeing 20 concurrent family relationships across varying stages of enrollment, maintaining full transparency on status and follow-up activities.
  • Guiding campus visits, shadow day experiences, and enrollment dialogues that articulate outcomes, expectations, and the model's intended audience with precision.
  • Keeping HubSpot CRM and student information system records current and accurate to enable forecasting, prioritization, and consistent service delivery.

What You Won’t Be Doing

  • Deploying transactional or aggressive sales methods.
  • Enrolling families whose needs or values are misaligned in order to meet a quota.
  • Overseeing a large team or navigating complex approval hierarchies.
  • Handing off accountability for the family experience to other team members.
  • Operating remotely. This position is campus-based by necessity.

Director Of Admissions And Enrollment Key Responsibilities

Lead and deliver a trust-centered, selectivity-driven enrollment process that successfully enrolls mission-aligned families while safeguarding the quality and outcomes of the Alpha model.

Basic Requirements

  • 3 years providing premium, individualized service in contexts where service excellence directly shapes brand perception (including education, luxury hospitality, executive support, premium membership, or owner-operated client services).
  • Proven ownership of a complete client, admissions, or enrollment experience from initial engagement through onboarding.
  • Experience managing 20 concurrent client, guest, or family relationships at varying stages, supported by a structured approach to tracking and prioritization.
  • Capacity to share specific examples of consultative guidance, including instances when you advised against your own offering because it was not the right match.
  • Professional writing experience with senior executives, high-net-worth individuals, or discerning clients.
  • Willingness to reside in or relocate within 60 days to one of the following locations: Greenwich, CT; Boca Raton, 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 selective private school admissions or enrollment for competitive programs.
  • Background in luxury hospitality, VIP client services, or executive support.
  • Experience designing or improving enrollment workflows, standard operating procedures, or service protocols.
  • Ability to leverage data and CRM analytics to enhance enrollment quality, not solely efficiency.

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-DirectorofAdmi1

Salary : $200,000

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