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

Unlike most enrollment positions that prioritize volume, this role is designed to uphold standards.

Alpha is constructing one of the world's most ambitious educational models. Our campuses integrate demanding academics, technology-driven instruction, and elevated expectations for both students and faculty. Students routinely demonstrate accelerated learning compared to national benchmarks, supported by measurable outcomes. Afternoons are dedicated to depth, autonomy, and practical skill development. The model delivers results. However, its success depends on enrolling the right families. Your role is critical to that outcome.

You will control the complete admissions process for a campus, spanning initial application to final enrollment. This is not a transitional or handoff position. You are accountable for the family experience, the clarity with which they comprehend the model, and ensuring enrollment decisions are made with proper rationale. You will evaluate compatibility, facilitate informed discussions, and advise against enrollment when appropriate. The objective is not maximizing numbers. The objective is ensuring alignment.

We welcome candidates from premium service sectors outside conventional education: selective private schools, competitive programs, high-end hospitality, executive assistance, exclusive membership organizations, or entrepreneurial operators who have directly managed sophisticated client relationships from inception to completion. What is essential is your capacity to execute a high-touch, multi-phase process with discernment, precision, and accountability. If your career has centered on delivering exceptional service where trust, confidentiality, and experience quality constitute the brand, this role will resonate. Apply now to apply that benchmark to meaningful work.

What You Will Be Doing

• Taking full ownership of the enrollment process for prospective families, beginning with initial contact and concluding with onboarding.
• Facilitating needs-assessment discussions to evaluate fit prior to offering solutions or advising on subsequent actions.
• Overseeing 20+ concurrent family relationships across various enrollment stages, maintaining transparent tracking of status and follow-up activities.
• Directing campus visits, shadowing opportunities, and decision-oriented conversations that articulate outcomes, expectations, and ideal candidate profiles.
• Ensuring precise CRM and enrollment documentation (HubSpot and SIS) to enable forecasting, prioritization, and service excellence.

What You Won’t Be Doing

• Employing transactional or aggressive sales methodologies.
• Accepting families who lack alignment merely to satisfy enrollment targets.
• Supervising a sizable team or operating within complex approval hierarchies.
• Transferring responsibility for the family experience across multiple functions.
• Working remotely. This position is campus-based by requirement.

Director Of Enrollment Key Responsibilities

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

Basic Requirements

• 3+ years providing premium, individualized service in settings where service excellence directly influences brand credibility (education, luxury hospitality, executive assistance, premium membership, or owner-managed services).
• Proven ownership of a complete client, admissions, or enrollment experience from initial contact through onboarding.
• Experience managing 20+ concurrent client, guest, or family relationships at varying stages, supported by a clear tracking and prioritization methodology.
• Capacity to offer specific examples of consultative decision-making, including instances where you recommended against your product or service due to poor fit.
• Professional writing experience engaging senior executives, high-net-worth individuals, or discerning clients.
• Willingness to reside in or relocate within 60 days to one of the following locations: Chicago, IL, Nashville, TN, Oklahoma City, OK, Tulsa, OK, or Southlake, TX.
• Authorized to work in the United States without visa sponsorship.

Nice-to-have Requirements

• Experience with selective private school admissions or enrollment in competitive programs.
• Background in luxury hospitality, VIP client services, or executive-level support functions.
• Experience designing or enhancing enrollment workflows, standard operating procedures, or service benchmarks.
• Proficiency leveraging data and CRM analytics to enhance conversion quality, 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-5800-US-Joliet-DirectorofEnro1