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

Crossover
Cleveland, OH Remote Full Time
POSTED ON 5/19/2026
AVAILABLE BEFORE 8/10/2026
Most enrollment positions prioritize throughput. This position prioritizes alignment.

Alpha is constructing a school model unlike any other at scale. Our campuses integrate academic rigor, technology-enhanced instruction, and elevated expectations for both learners and educators. Students advance more rapidly than national norms, supported by measurable outcomes. Afternoons shift toward mastery, autonomy, and applied competencies. The model delivers results. But only when families are correctly matched.

This is your responsibility.

You will manage the complete enrollment experience for a single campus, beginning with initial interest and concluding with onboarding. This is not a relay role. You determine how families perceive us, how well they grasp the model, and whether their enrollment choice reflects sound reasoning. You will evaluate compatibility, facilitate substantive dialogue, and advise against enrollment when appropriate. The objective is not volume maximization. The objective is strategic fit.

We welcome applicants from elite service sectors beyond conventional education: independent schools, competitive admissions programs, high-end hospitality, executive client management, premium membership platforms, or entrepreneurial operators who have directly overseen complex client experiences from start to finish. What counts is your capacity to execute a refined, phased engagement with discernment, precision, and accountability.

If your professional foundation is in delivering exceptional service where credibility, confidentiality, and experience design shape reputation, this opportunity will resonate—only now applied to work that measurably improves lives.

This is a full-time, salaried, on-site position. We are recruiting in Chicago, Nashville, Oklahoma City, Tulsa, Southlake, and Houston. Relocation assistance is provided.

What You Will Be Doing

  • Directing the entire enrollment pathway for prospective families, from initial outreach to final onboarding.
  • Facilitating discovery dialogues to assess alignment prior to proposing options or advising on progression.
  • Overseeing 20 concurrent family engagements across varied enrollment phases, with transparent tracking of status and next actions.
  • Orchestrating campus visits, student shadow days, and enrollment discussions that articulate results, standards, and intended audience with clarity.
  • Sustaining precise CRM and enrollment documentation (HubSpot and SIS) to enable forecasting, triage, and service excellence.

What You Won’t Be Doing

  • Deploying volume-driven or coercive enrollment strategies.
  • Accepting families with poor model alignment solely to achieve targets.
  • Supervising sizable teams or operating within multilayered hierarchies.
  • Distributing the family journey across multiple functional owners.
  • Operating remotely. This role is intentionally campus-resident.

Director Of Enrollment Management Key Responsibilities

Design and deliver a trust-based, selectivity-focused enrollment process that attracts aligned families while safeguarding the operational and academic integrity of the Alpha model.

Basic Requirements

  • 3 years providing premium, bespoke service in settings where client experience directly influences organizational credibility (education, luxury hospitality, executive support, premium membership, or owner-managed services).
  • Proven stewardship of a complete client, admissions, or enrollment cycle from initial engagement through onboarding completion.
  • Experience concurrently shepherding 20 client, guest, or family interactions across multiple stages, supported by a transparent management system.
  • Capacity to share specific instances of advisory decision-making, including occasions where you counseled against your own offering due to misalignment.
  • Professional correspondence experience with C-suite executives, affluent individuals, or discerning clientele.
  • Willingness to reside in or relocate within 60 days to one of these locations: Chicago, IL, Nashville, TN, Oklahoma City, OK, Tulsa, OK, Southlake, TX, or Houston, TX.
  • Authorized to work in the United States without visa sponsorship.

Nice-to-have Requirements

  • Experience in competitive independent school admissions or selective program recruitment.
  • Background in luxury hospitality, VIP concierge services, or executive client relations.
  • Experience designing or optimizing enrollment workflows, operating standards, or service protocols.
  • Proficiency leveraging data and CRM analytics to enhance enrollment quality, not solely 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-5800-US-Clevelan-DirectorofEnro

Salary : $200,000

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