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

Most enrollment positions focus on increasing headcount. This position focuses on upholding quality.

Alpha is developing one of the most forward-thinking school frameworks in the world. Our locations integrate demanding academics, technology-enabled instruction, and elevated expectations for both learners and educators. Students routinely progress faster than national averages, supported by measurable outcomes. Afternoons are structured for deeper engagement, autonomy, and practical competency development.

The framework is effective. But its effectiveness depends on enrolling the right families. That is your mandate.

You will control the admissions pathway for an entire campus, spanning initial application to final enrollment. This is not a role where responsibility is distributed. You determine how families engage with us, how thoroughly they grasp the framework, and whether their enrollment decisions reflect genuine alignment.

You will evaluate compatibility, facilitate intentional dialogue, and advise against enrollment when warranted. The objective is not enrollment maximization. The objective is mission alignment.

We welcome candidates from high-caliber service sectors outside conventional education: independent schools, competitive admissions programs, premium hospitality, executive concierge, exclusive membership platforms, or entrepreneurial operators who have directly stewarded high-stakes client experiences from start to finish.

What counts is your capacity to execute a personalized, multi-phase engagement with discernment, transparency, and accountability. If your career has centered on delivering exceptional service where credibility, confidentiality, and experiential excellence define reputation, this role will resonate. Apply now to elevate that expertise in work with lasting impact.

What You Will Be Doing

• Directing the complete enrollment pathway for prospective families, spanning initial outreach to onboarding completion.
• Facilitating discovery conversations to assess alignment before proposing options or advising on progression.
• Overseeing 20+ concurrent family engagements across varied enrollment phases, maintaining transparent tracking of status and follow-up timelines.
• Facilitating campus visits, student shadow days, and enrollment dialogues that articulate outcomes, expectations, and ideal candidate profiles.
• Ensuring precise CRM and enrollment documentation (HubSpot and SIS) to enable forecasting, strategic prioritization, and service excellence.

What You Won’t Be Doing

• Executing transactional or aggressive enrollment strategies.
• Admitting families lacking alignment merely to satisfy quotas.
• Overseeing staff or operating within bureaucratic decision hierarchies.
• Fragmenting family experience ownership across multiple stakeholders.
• Performing this work remotely. This position requires on-campus presence.

Director Of Enrollment Management Key Responsibilities

Direct and deliver a high-integrity, selective enrollment process that successfully enrolls mission-aligned families while safeguarding the rigor and outcomes of the Alpha framework.

Basic Requirements

• 3+ years providing premium, individualized service in contexts where service delivery directly shapes brand credibility (education, premium hospitality, executive assistance, exclusive membership, or privately operated service businesses).
• Proven ownership of a complete client, admissions, or enrollment experience from initial inquiry through successful onboarding.
• Experience managing 20+ concurrent client, guest, or family engagements at varying stages, supported by a reliable tracking and prioritization framework.
• Capacity to share specific examples of consultative judgment, including instances where you advised against your offering due to misalignment.
• Professional-grade written communication experience with executive leadership, affluent 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.
• Authorized to work in the United States without visa sponsorship.

Nice-to-have Requirements

• Background in competitive independent school admissions or selective program recruitment.
• Experience in premium hospitality, VIP client services, or executive support functions.
• Track record developing or optimizing enrollment workflows, standard operating procedures, or service protocols.
• Proficiency leveraging data and CRM analytics to enhance enrollment alignment, not merely volume.

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-Rockford-DirectorofEnro