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

While most enrollment positions prioritize volume, this role was designed to uphold standards.

Alpha is constructing one of the world's most ambitious educational models. Our campuses integrate demanding academics, technology-enabled instruction, and elevated expectations for both students and faculty. Students routinely exceed national learning benchmarks, with data to support these outcomes. Afternoon hours are dedicated to deeper exploration, independent work, and development of practical competencies. The model delivers results—but only when paired with the right families. That responsibility falls to you.

You will oversee the complete admissions process for a campus, spanning application to enrollment. This is not a role defined by handoffs. You are accountable for how families perceive us, how thoroughly they grasp the model, and whether enrollment choices are made with proper understanding. You will evaluate compatibility, facilitate meaningful dialogue, and advise against enrollment when circumstances warrant it. Maximum enrollment is not the objective. Alignment is.

We welcome candidates from premium service contexts outside conventional education: selective private institutions, competitive programs, upscale hospitality, executive assistance, exclusive membership communities, or entrepreneurs 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, transparency, and consistent follow-through. If your career has centered on delivering exceptional service where trust, confidentiality, and experiential quality define the brand, this position will resonate. Apply now to elevate that standard in work with lasting impact.

What You Will Be Doing

• Taking full ownership of the enrollment experience for prospective families, covering initial outreach through onboarding completion.
• Facilitating needs-assessment discussions to establish fit prior to offering solutions or suggesting subsequent actions.
• Coordinating 20+ concurrent family relationships across various enrollment phases, maintaining clear tracking of status and follow-up obligations.
• Directing campus visits, shadow day experiences, and decision-stage discussions that transparently convey results, expectations, and the model's ideal audience.
• Ensuring precise CRM and enrollment documentation (HubSpot and SIS) to enable forecasting, prioritization, and service excellence.

What You Won’t Be Doing

• Applying transactional or aggressive sales methods.
• Accepting families who represent poor alignment solely to achieve enrollment targets.
• Overseeing a sizable team or navigating complex approval hierarchies.
• Distributing responsibility for the family experience across multiple personnel.
• Operating remotely. This position is intentionally campus-based.

Director Of Enrollment Management Key Responsibilities

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

Basic Requirements

• 3+ years providing premium, individualized service in settings where service excellence directly influences brand standing (education, upscale hospitality, executive assistance, exclusive membership organizations, or owner-managed service businesses).
• Proven ownership of a complete client, admissions, or enrollment process spanning initial engagement through onboarding.
• Experience concurrently stewarding 20+ client, guest, or family accounts at varying stages, supported by a structured tracking and prioritization approach.
• Capacity to offer specific examples of consultative judgment, including instances where you advised against your offering when alignment was lacking.
• Professional written communication background with senior leaders, high-net-worth clientele, or discerning stakeholders.
• Willingness to reside in or relocate within 60 days to one of these locations: Greenwich, CT; Boca Raton, FL; Atlanta, GA; or Boston, MA.
• Authorized to work in the United States without visa sponsorship.

Nice-to-have Requirements

• Background in competitive private school admissions or enrollment for selective programs.
• Experience in upscale hospitality, VIP client services, or executive-level support functions.
• Track record developing or refining 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-5799-US-Lowell-DirectorofEnro