Demo

Director of Family Enrollment, Alpha - $200,000/year USD

Crossover
Chicago, IL Full Time
POSTED ON 4/9/2026
AVAILABLE BEFORE 5/7/2026
Many enrollment positions prioritize volume. This position exists to uphold standards.

Alpha is constructing one of the most forward-thinking school models globally. Our campuses integrate demanding academics, technology-enabled learning, and elevated expectations for both students and faculty. Students reliably progress faster than national averages, supported by measurable outcomes. Afternoon hours are dedicated to deeper exploration, independent work, and practical skill development. The model delivers results. But sustained success depends on enrolling aligned families.

This is your mandate.

You will oversee the complete enrollment process for a campus, beginning with the initial inquiry and continuing through onboarding. This is not a role where responsibility is passed between departments. 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 discussions, and advise against enrollment when appropriate. The objective is not filling seats. The objective is strategic alignment.

We welcome candidates from high-caliber service backgrounds outside conventional education: independent schools, competitive programs, upscale hospitality, executive assistance, exclusive membership organizations, or entrepreneurs who have directly managed premium client relationships from start to finish. The essential quality is your capacity to operate a meticulous, multi-phase process with sound judgment, precision, and consistent execution.

If your career has been defined by providing exceptional service where credibility, professionalism, and client experience shape the brand, this role will be recognizable—just directed toward work that produces measurable impact.

This is a full-time, salaried, on-site position. We are currently recruiting in Santa Barbara, Santa Monica, Orange County, Roswell, Chicago, Charlotte, Raleigh, and Dallas-Fort Worth. Support for relocation is provided.

What You Will Be Doing

  • Overseeing the entire enrollment experience for prospective families, from initial engagement through successful onboarding.
  • Facilitating exploratory discussions to evaluate alignment before proposing pathways or making recommendations.
  • Stewarding 20 concurrent family engagements across various stages of enrollment, maintaining transparent tracking and timely follow-up.
  • Guiding campus visits, student shadow days, and decision-making conversations that articulate results, standards, and ideal candidate profiles.
  • Ensuring precision in CRM and enrollment documentation (HubSpot and SIS) to enable accurate forecasting, task prioritization, and service excellence.

What You Won’t Be Doing

  • Applying transactional or aggressive sales techniques.
  • Accepting families who are poorly suited simply to meet enrollment targets.
  • Overseeing a sizable team or navigating complex hierarchical approvals.
  • Distributing accountability for the family journey across multiple team members.
  • Operating remotely. This role is intentionally campus-centered.

Director Of Family Enrollment Key Responsibilities

Lead and deliver a relationship-driven, standards-focused enrollment process that attracts well-matched families while safeguarding the integrity and effectiveness of the Alpha model.

Basic Requirements

  • 3 years providing high-caliber, individualized service in settings where the quality of service directly influences brand standing (education, upscale hospitality, executive assistance, premium membership, or independently operated services).
  • Proven ownership of a complete client, admissions, or enrollment experience from initial outreach through final onboarding.
  • Experience managing 20 concurrent client, guest, or family relationships across varying stages, supported by an organized tracking and prioritization approach.
  • Capacity to share specific examples of advisory decision-making, including instances where you counseled against your offering when alignment was absent.
  • Professional writing experience engaging senior leaders, affluent individuals, or discerning clients.
  • Willingness to reside in or relocate within 60 days to one of these locations: Santa Barbara, CA; Santa Monica, CA; Orange County, CA; Roswell, GA; Chicago, IL; Charlotte, NC; Raleigh, NC; or Dallas-Fort Worth, TX.
  • Authorized to work in the United States without visa sponsorship.

Nice-to-have Requirements

  • Experience in competitive private school admissions or enrollment for selective programs.
  • Background in upscale hospitality, VIP client services, or senior-level executive support.
  • Experience designing or enhancing enrollment workflows, standard operating procedures, or service benchmarks.
  • Proficiency leveraging data and CRM analytics to strengthen enrollment quality, not merely velocity.

About Alpha

Want to join a learning rebellion that’s transforming the traditional classroom?

Alpha School is on a mission to reshape education with a bold approach that harnesses AI to accelerate learning and unleash student potential.

They don’t play by the old rules.

Alpha is creating a new paradigm where students master core academics in just two hours a day, freeing up time for hands-on, passion-driven learning that truly prepares them for the real world.

Alpha School is rewriting the rules of education.

Sounds too good to be true? It’s not.

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-5531-US-Chicago-DirectorofFami

Salary : $200,000

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