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

Crossover


Date: 9 hours ago
City: Naperville, IL
Salary: $100 per hour
Contract type: Full time
Most enrollment positions are designed to maximize volume. This position is designed to uphold standards.

Alpha is developing one of the most ambitious educational models in the world. Our campuses integrate rigorous academics, technology-enabled learning, and elevated expectations for both students and staff. Students reliably outpace national learning benchmarks, supported by measurable data. Afternoons are reserved for depth, autonomy, and practical skill development. The model delivers results. But it delivers results only when paired with the right families. That is your responsibility.

You will direct the admissions process for a campus, spanning initial application to final enrollment. This is not a coordination role. You are accountable for how families perceive us, how thoroughly they grasp the model, and whether enrollment choices are grounded in alignment. You will evaluate compatibility, facilitate substantive discussions, and advise against enrollment when warranted. The objective is not enrollment maximization. The objective is mutual fit.

We welcome candidates from premium service sectors outside conventional education: selective private schools, competitive programs, high-end hospitality, executive assistance, premium membership organizations, or entrepreneurial operators who have directly managed high-value client relationships from start to finish. What matters is your capacity to execute a detailed, multi-phase process with discernment, precision, and accountability. If your career has been defined by delivering exceptional service where trust, discretion, and experiential quality shape the brand, this role will be intuitive. Apply now to apply that caliber of work to something meaningful.

What You Will Be Doing

  • Directing the complete enrollment experience for prospective families, spanning first touchpoint to onboarding completion.
  • Facilitating needs-based conversations to evaluate alignment before offering solutions or advising on next actions.
  • Overseeing 20+ concurrent family engagements across various enrollment stages, ensuring clear tracking and timely follow-through.
  • Guiding campus tours, student shadow visits, and enrollment dialogues that articulate outcomes, expectations, and model suitability with clarity.
  • Ensuring CRM and enrollment system accuracy (HubSpot and SIS) to enable forecasting, prioritization, and consistent service delivery.

What You Won’t Be Doing

  • Applying transactional or aggressive sales methods.
  • Accepting families who lack alignment merely to satisfy quotas.
  • Overseeing a sizable team or navigating complex hierarchical approval structures.
  • Distributing family experience ownership across multiple stakeholders.
  • Operating remotely. This position is campus-based by necessity.

Director Of Admissions And Enrollment Key Responsibilities

Direct and deliver a high-trust, highly selective enrollment process that successfully converts aligned families while safeguarding the integrity and educational performance of the Alpha model.

Basic Requirements

  • 3+ years providing premium, individualized service in settings where service excellence directly shapes brand reputation (education, high-end hospitality, executive support, premium membership organizations, or entrepreneurial service operations).
  • Proven ownership of a complete client, admissions, or enrollment process spanning initial contact through onboarding.
  • Experience managing 20+ concurrent client, guest, or family engagements at varying stages, supported by a structured tracking and prioritization approach.
  • Capacity to offer specific examples of consultative decision-making, including instances where you recommended against your offering when fit was absent.
  • Professional writing experience addressing senior executives, high-net-worth clients, or discerning audiences.
  • Willingness to reside in or relocate within 60 days to one of these markets: Chicago, IL, Nashville, TN, Oklahoma City, OK, Tulsa, OK, or Southlake, TX.
  • Authorized to work in the United States without requiring visa sponsorship.

Nice-to-have Requirements

  • Experience in competitive private school admissions or selective program enrollment.
  • Background in high-end hospitality, VIP client services, or executive support functions.
  • Experience developing or enhancing enrollment workflows, standard operating procedures, or service protocols.
  • Proficiency leveraging data and CRM analytics to enhance conversion alignment, not merely conversion speed.

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-Napervil-DirectorofAdmi.004

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