Head of School, Alpha - $400,000/year USD

Crossover; Vermont; On-site; USD 360,000 - 440,000; Full time

Job summary

Alpha is hiring a Head of School to lead the parent-facing side in multiple U.S. metros, including Burlington (VT), Miami, Irvine, and Los Angeles.

The role centers on enrollment growth, UHNW advocacy, and preserving the school model while managing escalations with influential families. With 7+ years in high-stakes education or wealth-adjacent leadership and a track record of converting inquiries into enrollments, you will partner with private offices and high-net-worth networks to build a

Qualifications

• 7+ years leading high-stakes relationships in private or independent education, fundraising, or wealth management.
• 2+ years working directly with ultra-high-net-worth families or similar high-expectation groups.
• Proven ownership of measurable enrollment, retention, advocacy, or client outcomes.
• Polished executive communication and conviction in Alpha's model.
• Residence in listed metro areas (MIAMI, Irvine, Park City, Boca Raton, Palm Beach, Tulsa, Austin, LA, Burlington VT, Las Vegas, Jackson Hole, Bay Area).

Responsibilities

• Build local awareness through partnerships with family offices, private clubs, and independent advisors.
• Run admissions for wealthy families end-to-end: info sessions, follow-ups, enrollment decision.
• Turn enrolled families into public champions of 2 Hour Learning through advocacy workshops.
• Resolve escalations by diagnosing model vs. campus vs. family-fit issues and write precedents.
• Maintain strong relationships with current families and report patterns to leadership.

Skills

High-stakes relations

UHNW client experience

Enrollment outcomes

Executive communication

Residence in metros

Job description

"We are never going to lower the standard for any kid — instead we're going to raise the support to help them get there."

— Braden, Head Guide, Alpha Austin

Alpha is hiring.

You went into school leadership to shape how children learn, not to run capital campaigns and referee parent committees. There is a version of this job where the academic model is protected for you, operations is handled centrally, and you spend your week on what you do best: winning over the families who matter most, turning them into advocates, and being the voice of authority when the conversation gets hard.

You will own the parent side of Alpha in one metro — Miami, San Francisco, Irvine, Park City, Boca Raton, Palm Beach, Tulsa, Lake Travis, Lake Forest, Burlington, Las Vegas, Jackson Hole, San Rafael, or Los Angeles. Your measure is enrollment and advocacy: prospective ultra-high-net-worth families who convert, current UHNW families who re-enroll, refer, and publicly champion 2 Hour Learning, and a local community where Alpha is top of mind. Roughly half your week is outward-facing — community partnerships, info sessions, and 1:1 conversations with sophisticated parents who have read every AI skeptic and want to know why the model actually works.

The rest of the seat is the escalation line. When a board family threatens to pull their kids, or a campus quietly softens the model to keep a vocal parent happy—it comes to you. You retain the family, and you keep the model intact. Both. Then you document the precedent so the network can handle it next time without you.

If you have run a private or independent K-12 school, or you have spent a career earning the trust of UHNW families in another industry, and you have been waiting for the job where judgment and persuasion are the actual deliverables, this is it.

What You Will Be Doing

• Building local awareness through partnerships with family offices, private clubs, and independent advisors, plus workshops and community events that generate inbound interest
• Running admissions for wealthy families end to end: info sessions, 1:1 follow-up in the CRM, and the enrollment decision, including telling a family this is not the right school for their child
• Turning enrolled parents into public champions of 2 Hour Learning through advocacy workshops and parent-to-parent networks, so enrolled families become your strongest source of new inquiries
• Resolving the escalations others cannot: diagnosing whether the problem is the model, campus execution, or family fit, engaging the family directly, then writing up the precedent for the rest of the network
• Keeping current families close through regular touchpoints, and reporting the patterns you hear back to leadership

What You Won’t Be Doing

• Running capital campaigns, donor cultivation, major gifts, or any other form of fundraising
• Convening PTAs, School Improvement Councils, parent committees, or focus groups that get a vote on school policy
• Managing facilities, finance, legal, vendors, technology, marketing, or community logistics — centralized teams own all of this, so your week stays on relationships, not operations
• Designing curriculum or coaching instructional staff on pedagogy; the academic model is owned and protected centrally
• Making exceptions or customizations to the educational model to satisfy a parent request, however influential the parent
• Simply logging and responding to complaints, or writing newsletters and routine parent communications
• Defusing conflict by avoiding it — diplomacy here means delivering hard messages, not softening standards
• Working behind the scenes; this is an on-site, full-time, face-of-the-school seat that includes evening and weekend community events

Head Of School Key Responsibilities

Build a metro where Alpha families are 2 Hour Learning’s loudest advocates — and where no parent crisis is resolved by compromising the model.

Basic Requirements

• 7+ years leading high-stakes relationships in private or independent K-12 education, fundraising or major gifts, enterprise sales, client success, or private wealth management
• 2+ years working directly and regularly with ultra-high-net-worth or similarly high-expectation families, such as full-pay families at an elite private school, family-office clients, wealth-management clients, or major donors
• Proven ownership of measurable enrollment, retention, advocacy, sales, or client outcomes, including resolving sensitive situations and holding firm standards when influential people push back
• Polished executive communication, consultative judgment, and genuine conviction in Alpha's accelerated learning model, with the confidence to represent it to skeptical parents and public stakeholders
• Living in the Miami, Irvine, Park City, Boca Raton, Palm Beach, Tulsa, Austin, Los Angeles, Burlington (VT), Las Vegas, Jackson Hole, or Bay Area metro area
• Authorized to work in the United States without sponsorship; and available for full-time on-site work, including 2 to 4 evening or weekend events per month

Nice-to-have Requirements

• Sitting or recent Head of School — or the Head’s right hand — at a top-tier independent K-12 (NAIS-member or peer tier)
• Multi-campus or multi-site school leadership experience (regional director, network superintendent, COO of a school network)
• A UHNW client-services background translated into school leadership: private wealth management, single-family office, or major-gifts development at an elite prep or Ivy
• An existing network among UHNW families or influential local organizations in Miami, San Francisco, Irvine, Park City, Boca Raton, Palm Beach, Tulsa, Lake Travis, Lake Forest, Burlington, Las Vegas, Jackson Hole, San Rafael, or Los Angeles
• Crisis communication experience involving press, regulators, or board-level stakeholders
• Hands-on AI building experience — custom GPTs, agents, or vibe-coded internal tools used in a real operating context
• An advanced degree (M.Ed., MBA, or doctorate) — common in this profile, but not required; no formal education is required for this role

About Alpha

Join the team building school around student growth

Alpha reimagines the school day around faster learning, stronger mentorship, and more time for students to build real-world skills.

Roles with real student impact:

Alpha hires teachers (guides), operators, admissions experts, school & curriculum leaders, and remote team members.

Education work that pays like it matters:

Alpha offers six-figure roles for people ready to help build a radically better school experience.

A culture built for builders:

Alpha is fast-moving, ambitious, and student focused. It’s for people who want to improve the system, not maintain it.

Alpha is where you can do the most meaningful work of your career.

There is so much to cover for this exciting role, and space here is limited.

Working with us

This is a full-time, W2 employee position with immediate access to benefits (https://support.crossover.com/article/7581-w2-benefits-u-s-paychex-paid-only). All roles are year-long positions. The compensation level for this role is $400,000 USD/year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.