Director of Community Engagement, 2 Hour Learning - $400,000/year USD

About the role

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.

Responsibilities

• 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

Requirements

• 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

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, 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