Crossover Learning Jobs in Chicago, IL (NOW HIRING)

You went into private 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 are best at: 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, 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 an Associate Dean of Parents reaches the edge of what they can resolve — a board family threatening to pull their kids, a campus quietly softening 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 Associate Dean 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.

• 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

• Fundraising of any kind is off your plate — no capital campaigns, donor cultivation, or major gifts
• 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

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

• 7+ years in a role built on high-stakes relationships: head of school, fundraising, enterprise sales, private wealth management, or client success
• Direct, repeated work with ultra-high-net-worth (UHNW) families, such as households earning $1M+ a year or families paying full tuition at an elite private school
• Experience in a parent-facing or client-facing role at an independent or private K-12 school, or in UHNW client services
• At least one example of personally leading a sensitive situation to resolution: a parent crisis, a staff investigation, a press inquiry, or a regulator interaction
• A track record of holding a standard when influential people push back on it
• Living in the Miami, San Francisco, or Los Angeles metro area, and able to work on-site full-time, including evening and weekend events
• Authorized to work in the United States without sponsorship

• 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, 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

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, 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.

Crossover Job Code: LJ-5465-US-Chicago-HeadofSchool.007