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

Many enrollment positions prioritize volume. This position prioritizes standards.

Alpha is constructing a school model that ranks among the most ambitious globally. Our campuses integrate rigorous academics with technology-enabled learning and maintain elevated expectations for both students and educators. Student learning velocity consistently exceeds national benchmarks, supported by measurable data. Afternoons are allocated to depth work, independent learning, and practical skill development. The model is effective. Its effectiveness, however, depends entirely on enrolling the right families. That responsibility is yours.

You will control the entire admissions process for a campus, beginning with the application and concluding with enrollment. This is not a role with fragmented ownership. You are accountable for the family experience, the clarity with which they understand our model, and the soundness of their enrollment decision. You will evaluate compatibility, facilitate substantive dialogue, and advise against enrollment when appropriate. The objective is not to maximize enrollment figures. The objective is to ensure alignment.

We welcome candidates whose backgrounds include premium service delivery outside conventional education: selective private schools, competitive programs, upscale hospitality, executive assistance, exclusive membership organizations, or entrepreneurial operators who have directly managed high-value client experiences from start to finish. What counts is your capacity to execute a sophisticated, multi-phase process with discernment, precision, and accountability. If your career has been defined by delivering exceptional service where trust, discretion, and experiential quality constitute the brand, this role will resonate. Apply now to apply that standard to meaningful work.

What You Will Be Doing

• Controlling the complete enrollment experience for prospective families, spanning initial contact through onboarding completion.
• Facilitating needs-assessment discussions to establish fit prior to introducing solutions or advising on subsequent actions.
• Overseeing 20+ concurrent family engagements across various enrollment stages, maintaining transparent tracking and follow-up protocols.
• Directing campus visits, shadow day experiences, and decision-oriented conversations that articulate outcomes, expectations, and model suitability with clarity.
• Ensuring precise CRM and enrollment documentation (HubSpot and SIS) to enable forecasting accuracy, prioritization, and service excellence.

What You Won’t Be Doing

• Employing transactional or aggressive sales methodologies.
• Admitting families who do not align with the model solely to achieve enrollment targets.
• Overseeing a sizable team or operating within complex hierarchical approval structures.
• Distributing responsibility for the family journey across multiple staff members.
• Performing this work remotely. This position requires on-campus presence by design.

Director Of Enrollment Management Key Responsibilities

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

Basic Requirements

• 3+ years providing premium, tailored service in settings where service excellence directly influences brand perception (education, upscale hospitality, executive assistance, exclusive membership, or owner-operated services).
• Proven ownership of a complete client, admissions, or enrollment process from initial engagement through onboarding.
• Experience concurrently stewarding 20+ client, guest, or family accounts across varying stages, supported by a reliable tracking and prioritization framework.
• Capacity to furnish specific examples of consultative judgment, including instances where you advised against your product or service due to poor fit.
• Professional-grade written communication experience with senior leadership, high-net-worth clients, or discerning stakeholders.
• Willingness to reside in or relocate within 60 days to one of these locations: Chicago, IL, Nashville, TN, Oklahoma City, OK, Tulsa, OK, or Southlake, TX.
• Authorization to work in the United States without requiring visa sponsorship.

Nice-to-have Requirements

• Experience in competitive private school admissions or selective program enrollment processes.
• Professional history in upscale hospitality, VIP client services, or executive-level assistance.
• Experience designing or refining enrollment workflows, standard operating procedures, or service protocols.
• 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-DirectorofEnro.001