Head of Admissions, 2 Hour Learning - $200,000/year USD (Chicago)

While most enrollment positions prioritize volume, this role exists to safeguard standards.

Alpha is developing one of the world's most ambitious school models. Our campuses integrate rigorous academics, technology-enhanced learning, and elevated expectations for both students and faculty. Students routinely exceed national learning benchmarks, supported by verifiable data. Afternoons are reserved for deep learning, independence, and practical skill development. The model delivers results. But success depends entirely on selecting the right families. That's your responsibility.

You will control the complete admissions process for a campus, from initial application to final enrollment. This is not a role where you hand off responsibilities. You are accountable for the family experience, for ensuring families fully comprehend our model, and for confirming enrollment decisions are made for sound reasons. You will evaluate compatibility, facilitate substantive discussions, and recommend declining candidates when appropriate. Maximum enrollment is not the objective. The objective is proper alignment.

We welcome candidates from premium service backgrounds outside conventional education: selective private schools, competitive programs, high-end hospitality, executive support, exclusive membership organizations, or owner-operators who have directly managed high-value client relationships from beginning to end. What counts is your capacity to execute a sophisticated, multi-phase process with sound judgment, transparency, and consistent follow-through. If your career has been defined by delivering exceptional service where trust, discretion, and experience quality shape the brand, this position will resonate.

What You Will Be Doing

• Controlling the complete enrollment experience for prospective families, from initial contact to onboarding completion.
• Facilitating needs-assessment discussions to establish fit prior to proposing solutions or advising on next steps.
• Overseeing 20+ concurrent family relationships at varying enrollment stages, with transparent tracking of status and follow-up actions.
• Directing campus tours, shadow experiences, and decision-focused conversations that articulate outcomes, expectations, and the model's ideal audience.
• Keeping CRM and enrollment data accurate (HubSpot and SIS) to enable forecasting, prioritization, and service excellence.

What You Won’t Be Doing

• Employing transactional or aggressive sales methods.
• Accepting misaligned families solely to meet enrollment targets.
• Overseeing a large team or navigating complex approval hierarchies.
• Distributing family experience ownership across multiple roles.
• Operating remotely. This position is campus-based by necessity.

Head Of Admissions Key Responsibilities

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

Basic Requirements

• 3+ years providing premium, individualized service in settings where service quality directly influences brand reputation (education, high-end hospitality, executive support, exclusive membership, or owner-operated services).
• Proven ownership of a complete client, admissions, or enrollment process from initial contact to onboarding.
• Experience managing 20+ concurrent client, guest, or family relationships at various stages, supported by a clear tracking and prioritization system.
• Capacity to share specific examples of consultative decision-making, including instances where you advised against your product or service due to poor fit.
• Professional written communication experience with senior executives, high-net-worth individuals, or sophisticated clientele.
• Willingness to reside in or relocate within 60 days to one of these markets: Chicago, IL, Nashville, TN, or Tulsa, OK.
• Authorized to work in the United States without visa sponsorship.

Nice-to-have Requirements

• Experience in selective private school admissions or competitive program recruitment.
• Background in high-end hospitality, VIP guest services, or executive-level support functions.
• Experience developing or refining enrollment workflows, standard operating procedures, or service benchmarks.
• Comfort leveraging data and CRM insights to enhance conversion quality, 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.

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 for more details on this topic.

Crossover Job Code: LJ-5800-US-Chicago-HeadofAdmissio.005