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

Unlike most enrollment positions designed to maximize numbers, this role exists to uphold standards.2 Hour Learning partners with families who demand precision, discretion, and verifiable results. We condense a traditional full school day into two highly focused hours through AI-powered, mastery-based instruction. Students routinely outpace national learning benchmarks, supported by data. Afternoons are freed for depth, autonomy, and practical skill development. The model delivers results. But success depends entirely on selecting the right families.This is your mandate.You will manage the complete enrollment experience for a campus, starting with initial inquiry and continuing through onboarding. This is not a role where responsibility is shared. You own how families perceive us, how clearly they grasp the model, and whether enrollment decisions are made with appropriate reasoning. You will evaluate fit, facilitate meaningful dialogue, and advise against enrollment when necessary. Maximum enrollment is not the objective. Alignment is.We welcome candidates from premium service sectors outside conventional education: selective private schools, competitive programs, luxury hospitality, executive services, premium membership communities, or owner-operators who have directly managed high-value client experiences from start to finish. What counts is your capacity to execute a high-touch, multi-phase process with discernment, clarity, and consistent follow-through.If your career has centered on delivering white-glove service where trust, discretion, and experience quality shape the brand, this role will feel natural—applied to work that genuinely transforms outcomes.This is a full-time, salaried, on-site position. We are currently hiring in Dallas-Fort Worth, Austin, Santa Barbara, San Francisco, Orange County, and Palm Beach. Relocation assistance is provided.What You Will Be DoingManaging the complete enrollment process for prospective families, from initial contact through final onboarding.Facilitating needs-assessment discussions to evaluate fit before proposing solutions or advising on next steps.Overseeing 20+ concurrent family relationships across various stages of the enrollment cycle, maintaining clear tracking and timely follow-ups.Delivering campus tours, shadow day experiences, and decision-stage conversations that articulate outcomes, expectations, and model suitability.Keeping CRM and enrollment systems (HubSpot and SIS) current and accurate to enable forecasting, prioritization, and service excellence.What You Won’t Be DoingApplying transactional or high-pressure sales methods.Enrolling misaligned families to meet numerical targets.Supervising a sizable team or navigating complex approval hierarchies.Transferring ownership of the family experience across multiple roles.Working remotely. This position is campus-based by necessity.Enrollment Director Key ResponsibilitiesDesign and deliver a high-trust, selective enrollment process that successfully converts aligned families while safeguarding the integrity and effectiveness of the 2 Hour Learning model.Basic Requirements3+ 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 complete 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 clear tracking and prioritization system.Ability to supply specific examples of consultative decision-making, including instances where you recommended against your product or service due to poor fit.Professional written communication history with senior executives, high-net-worth individuals, or sophisticated clients.Willingness 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.Nice-to-have RequirementsExperience in competitive private school admissions or selective program enrollment.Background in luxury hospitality, VIP guest relations, or executive-level support functions.Experience developing or refining enrollment workflows, standard operating procedures, or service standards.Comfort leveraging data and CRM insights to enhance conversion quality, not merely velocity.About 2 Hour LearningEducation 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 usThis 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-5531-US-Boston-EnrollmentDire.017