Dean of Enrollment, Learning

Many enrollment positions focus on driving numbers. This position is designed to uphold rigor. 2 Hour Learning partners with families seeking precision, confidentiality, and verifiable results. We distill a complete school day into two highly focused hours through AI-enabled, mastery-based instruction. Students routinely outpace national learning benchmarks, supported by measurable data. Afternoons become available for deeper exploration, autonomy, and practical skill development.

The model is effective, but its success depends entirely on family alignment.

• Managing the complete enrollment cycle for prospective families, starting from initial inquiry and continuing through onboarding.
• Facilitating assessment-focused conversations to evaluate alignment before introducing solutions or advising on progression.
• Overseeing 20+ concurrent family engagements across various enrollment phases, maintaining clear tracking of status and scheduled follow-up.
• Directing campus visits, shadow day experiences, and decision‑oriented dialogues that articulate outcomes, expectations, and ideal candidate profiles.
• Ensuring precise CRM and enrollment documentation (Hub Spot and SIS) to enable accurate forecasting, strategic prioritization, and consistent service delivery.

• Applying transactional or coercive sales methods.
• Accepting families with poor alignment solely to satisfy enrollment targets.
• Supervising extensive teams or navigating multi‑tier authorization processes.
• Transferring responsibility for family engagement across multiple departments.
• Operating remotely. This position requires on‑campus presence by design.

Execute and manage a high‑integrity, selective enrollment process that successfully enrolls compatible families while safeguarding the academic credibility and operational effectiveness of the 2 Hour Learning model.

• 3+ years providing premium, individualized service in settings where quality of service directly influences brand standing (education, luxury hospitality, executive support, premium membership, or independently owned service businesses).
• Proven ownership of a complete client, admissions, or enrollment process spanning first interaction through onboarding.
• Experience concurrently managing 20+ client, guest, or family relationships across varying stages, supported by a structured approach to tracking and prioritization.
• Capacity to supply specific examples of consultative decision‑making, including instances where you advised against your offering when alignment was lacking.
• Professional writing experience addressing senior executives, high‑net‑worth individuals, or discerning clientele.
• Readiness to reside in or relocate within 60 days to one of these markets:
  Santa Barbara, CA;
  San Francisco, CA;
  Orange County, CA;
  Dallas‑Fort Worth, TX; or Palm Beach, FL.
• Authorization to work in the United States without requiring visa sponsorship.

• Background in selective independent school admissions or competitive program recruitment.
• Experience in luxury hospitality, VIP client services, or executive support capacities.
• Involvement in developing or enhancing enrollment workflows, standard operating procedures, or service protocols.
• Proficiency leveraging data and CRM analytics to enhance enrollment quality, not merely velocity.

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.

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.