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Head of Enrollment Operations, Learning

Job in Santa Barbara, Santa Barbara County, California, 93190, USA
Listing for: Crossover
Full Time, Part Time position
Listed on 2026-02-28
Job specializations:
  • Business
    Customer Success Mgr./ CSM
Salary/Wage Range or Industry Benchmark: 200000 USD Yearly USD 200000.00 YEAR
Job Description & How to Apply Below
Position: Head of Enrollment Operations, 2 Hour Learning - $200,000/year USD

LOCATION

NOTE:

We are hiring multiple candidates for this position. This is an in-person role based at our campuses in Dallas-Fort Worth, Austin, Santa Barbara, San Francisco, Orange County, and Palm Beach. Relocation assistance is provided.

Most enrollment functions prioritize volume. This one prioritizes standards.

At 2 Hour Learning, we serve families who demand precision, discretion, and evidence. We condense a complete school day into two concentrated hours through AI-powered, mastery-based learning. Students routinely outpace national learning benchmarks, supported by verifiable data. Afternoons are freed for depth, autonomy, and real-world skill development. The model is effective. But it requires the right families.

This is your responsibility.

You will manage the complete enrollment experience for a campus, starting with initial inquiry and continuing through onboarding. This is not a handoff position. You are accountable for how families perceive us, how well they comprehend the model, and whether enrollment decisions are made for sound reasons. You will evaluate fit, facilitate thoughtful discussions, and advise against enrollment when appropriate. The objective is not to maximize enrollment.

The objective is alignment.

We welcome candidates from premium service backgrounds outside traditional education: private schools, selective programs, luxury hospitality, executive support, premium membership organizations, or owner-operators who have directly managed high-value client experiences end-to-end. What counts is your capacity to execute a high-touch, multi-phase process with judgment, clarity, and accountability.

If your career has been built on delivering white-glove service where trust, discretion, and experience quality define brand value, this role will be recognizable—just directed toward something that produces measurable outcomes.

This is a full-time, salaried, in-person position. We are hiring across Dallas-Fort Worth, Austin, Santa Barbara, San Francisco, Orange County, and Palm Beach. Relocation assistance is available.

What You Will Be Doing
  • Managing the complete enrollment journey for prospective families, from initial contact through onboarding.
  • Facilitating needs-assessment discussions to establish fit before proposing solutions or suggesting next steps.
  • Overseeing 20+ concurrent family relationships across various stages of the enrollment process, with transparent tracking of status and follow-up actions.
  • Conducting campus tours, shadow experiences, and decision-oriented conversations that articulate outcomes, expectations, and the model's ideal audience.
  • Ensuring accurate CRM and enrollment documentation (Hub Spot and SIS) to enable forecasting, prioritization, and service excellence.
What You Won’t Be Doing
  • Applying transactional or high-pressure sales methods.
  • Enrolling misaligned families to satisfy a target.
  • Supervising a large team or working through layered approval structures.
  • Distributing ownership of the family experience across multiple roles.
  • Operating remotely. This role is campus-based by design.
Head Of Enrollment Operations

Key Responsibilities

Own and deliver a high-trust, high-selectivity enrollment experience that converts aligned families while safeguarding the integrity and performance of the 2 Hour Learning model.

Basic Requirements
  • 3+ years providing premium, personalized service in settings where service quality directly influences brand reputation (education, luxury hospitality, executive support, premium membership, or owner-operated services).
  • Proven ownership of a full client, admissions, or enrollment process from initial contact through onboarding.
  • Experience managing 20+ client, guest, or family relationships concurrently at varying stages, supported by a structured 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 clients.
  • Willingness to reside in or relocate within 60 days to Santa Barbara, CA;
    San…
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