Head of School $400,000 USD/year Pay is set based on global value, not the local market.
Most roles = hourly rate x 40 hrs x 50 weeks
Description
You pursued leadership in private education to influence how children are taught, not to oversee fundraising drives or mediate parent advisory groups. This version of the role protects the academic framework for you, centralizes operational management, and allows you to focus your time on what you do best: attracting the families who matter most, converting them into advocates, and serving as the definitive voice when difficult conversations arise.
You will lead the parent engagement side of Alpha in a single metro area — either Miami, San Francisco, or Los Angeles. Success will be measured by enrollment and advocacy: prospective ultra-high-net-worth families who enroll, current UHNW families who re-enroll, refer others, and publicly champion 2 Hour Learning, and a local presence where Alpha is recognized and respected. Approximately half your time will be externally focused — forming community partnerships, hosting information sessions, and conducting 1:1 discussions with discerning parents who have examined every AI critique and want to understand why this model truly delivers.
The other half of your role serves as the escalation channel. When an Associate Dean of Parents encounters a situation beyond their authority — a prominent family threatening withdrawal, a campus quietly modifying the model to appease a vocal parent — it escalates to you. Your responsibility is to retain the family and preserve the model. Both outcomes. Then you create documentation of the resolution so the Associate Dean network can manage similar cases independently going forward.
If you have led a private or independent K-12 school, or if you have built a career earning the confidence of UHNW families in another sector, and you have been seeking the role where sound judgment and persuasive communication are the core deliverables, this is that opportunity.
What you will be doing
- Establishing local visibility through relationships with family offices, private clubs, and independent advisors, plus hosting workshops and community events that drive inbound interest
- Managing the complete admissions process for affluent families: conducting info sessions, executing 1:1 follow-up in the CRM, and making enrollment decisions, including advising a family when this is not the appropriate school for their child
- Converting enrolled parents into vocal advocates of 2 Hour Learning through advocacy workshops and parent-to-parent networks, ensuring enrolled families become your most effective source of new leads
- Handling escalations beyond others' capacity: determining whether the issue stems from the model, campus implementation, or family alignment, engaging directly with the family, then documenting the resolution for network-wide reference
- Maintaining consistent contact with current families through regular touchpoints, and communicating the themes you observe back to leadership
What you will NOT be doing
- Leading capital campaigns, donor cultivation, major gifts, or any other fundraising activities
- Organizing PTAs, School Improvement Councils, parent committees, or focus groups that influence school policy through voting
- Overseeing facilities, finance, legal, vendors, technology, marketing, or community logistics — centralized teams manage all of this, keeping your schedule focused on relationships, not operations
- Developing curriculum or mentoring instructional staff on teaching methods; the academic model is centrally owned and protected
- Granting exceptions or modifications to the educational model to accommodate a parent request, regardless of the parent's influence
- Merely logging and answering complaints, or drafting newsletters and routine parent communications
- Resolving conflict through avoidance — diplomacy in this role means delivering difficult messages, not diluting standards
- Operating behind the scenes; this is an on-site, full-time, public-facing school leadership position that includes evening and weekend community events
Key responsibilities
Develop a metro area where Alpha families serve as 2 Hour Learning's most vocal advocates — and where no parent crisis is resolved by weakening the model.
Candidate requirements
- 7+ years in a position centered on high-stakes relationships: head of school, fundraising, enterprise sales, private wealth management, or client success
- Direct, sustained experience with ultra-high-net-worth (UHNW) families, such as households earning $1M+ annually or families paying full tuition at an elite private school
- Experience in a parent-facing or client-facing capacity at an independent or private K-12 school, or in UHNW client services
- At least one instance of personally guiding a sensitive situation to resolution: a parent crisis, a staff investigation, a press inquiry, or a regulator interaction
- A demonstrated history of upholding a standard when influential individuals challenge it
- Residing in the Miami, San Francisco, or Los Angeles metro area, and available to work on-site full-time, including evening and weekend events
- Authorized to work in the United States without sponsorship
Nice to have
- Current or recent Head of School — or the Head's principal deputy — at a top-tier independent K-12 (NAIS-member or equivalent tier)
- Multi-campus or multi-site school leadership experience (regional director, network superintendent, COO of a school network)
- A UHNW client-services background applied to school leadership: private wealth management, single-family office, or major-gifts development at an elite preparatory school or Ivy League institution
- An established network among UHNW families or influential local organizations in Miami, San Francisco, or Los Angeles
- Crisis communication experience involving press, regulators, or board-level stakeholders
- Practical AI development experience — custom GPTs, agents, or vibe-coded internal tools deployed in a real operating environment
- An advanced degree (M.Ed., MBA, or doctorate) — common in this profile, but not required; no formal education is required for this role
Applying for a role? Here’s what to expect.
Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.
Chat-style
screening interview.
Cognitive 
aptitude test.
Prove real-world 
job skills.
Interview with the hiring manager.
Pass
proctored test.
Accept job offer.
Frequently asked questions
About the role
Reviews
Meet some people who've landed similar jobs
Recruitment sucks. So we’re fixing it.
The Olympics of work
It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.
Premium pay for premium talent
Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.
Shortlist by skills, not bias
We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.
Join the world's largest community of 
AI-first remote workers.