Director of Community Engagement $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 entered private school leadership to influence how students learn—not to manage capital campaigns or mediate parent committees. A version of this role exists where the academic model is safeguarded for you, operations are centrally managed, and your time is dedicated to what you do best: engaging the families who matter most, converting them into advocates, and serving as the authoritative voice when conversations become challenging.
You will lead the parent-facing side of Alpha in a single metropolitan area—Miami, San Francisco, or Los Angeles. Success is measured by enrollment and advocacy: ultra-high-net-worth prospective families who enroll, current UHNW families who re-enroll, refer others, and publicly endorse 2 Hour Learning, and a local market where Alpha is a recognized priority. Approximately half your time will be externally focused—community partnerships, information sessions, and one-on-one discussions with discerning parents who have reviewed every AI critique and seek to understand why the model is sound.
The remainder of your role functions as the escalation point. When an Associate Dean of Parents encounters a challenge beyond their capacity—a board-level family threatening withdrawal, or a campus quietly adjusting the model to accommodate a vocal parent—the issue escalates to you. You will retain the family while preserving the model. Both outcomes are required. You will then document the resolution so the Associate Dean network can manage similar cases independently in the future.
If you have led a private or independent K-12 school, or if you have built a career earning the trust of UHNW families in another sector, and you have been seeking a position where judgment and persuasion are the core deliverables, this role is designed for you.
What you will be doing
- Cultivating local visibility through alliances with family offices, private clubs, and independent advisors, alongside workshops and community initiatives that drive inbound interest
- Managing the full admissions cycle for affluent families: conducting information sessions, following up individually via CRM, and making enrollment decisions—including advising a family when the school is not the appropriate fit for their child
- Converting enrolled parents into vocal advocates for 2 Hour Learning by facilitating advocacy workshops and parent-to-parent networks, ensuring that current families become your primary source of new inquiries
- Handling escalations that others cannot resolve: determining whether the root cause is the model, campus implementation, or family alignment, engaging directly with the family, and then documenting the resolution for the broader network
- Maintaining consistent engagement with current families through regular outreach, and communicating observed patterns back to leadership
What you will NOT be doing
- Leading capital campaigns, donor outreach, major gift initiatives, or any fundraising activities
- Organizing PTAs, School Improvement Councils, parent committees, or focus groups that influence school policy decisions
- Overseeing facilities, finance, legal, vendors, technology, marketing, or community logistics—centralized teams manage all of these, allowing you to focus on relationships rather than operations
- Developing curriculum or providing pedagogical coaching to instructional staff; the academic model is centrally owned and protected
- Granting exceptions or modifications to the educational model to accommodate parent requests, regardless of the parent's influence
- Merely documenting and replying to complaints, or drafting newsletters and routine parent correspondence
- Resolving conflict through avoidance—diplomacy in this role requires delivering difficult messages, not diluting standards
- Operating remotely; this is an on-site, full-time, public-facing position that includes evening and weekend community engagements
Key responsibilities
Establish a metro area where Alpha families serve as 2 Hour Learning's most vocal advocates—and where no parent crisis is resolved by compromising the model.
Candidate requirements
- 7+ years in a role centered on high-stakes relationships: head of school, fundraising, enterprise sales, private wealth management, or client success
- Consistent, direct engagement with ultra-high-net-worth (UHNW) families, such as households with $1M+ annual income or families paying full tuition at elite private schools
- Experience in a parent-facing or client-facing capacity at an independent or private K-12 school, or within UHNW client services
- At least one documented example 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 stakeholders challenge it
- Current residence in the Miami, San Francisco, or Los Angeles metro area, with the ability to work on-site full-time, including evening and weekend events
- Authorization to work in the United States without sponsorship
Nice to have
- Current or recent Head of School—or senior leadership deputy—at a top-tier independent K-12 institution (NAIS-member or equivalent)
- Leadership experience across multiple campuses or sites (regional director, network superintendent, COO of a school network)
- A UHNW client-services background successfully transitioned into school leadership: private wealth management, single-family office, or major-gifts fundraising at an elite preparatory school or Ivy League institution
- An established network among UHNW families or prominent local organizations in Miami, San Francisco, or Los Angeles
- Crisis communication experience involving the press, regulators, or board-level stakeholders
- Practical AI development experience—custom GPTs, agents, or vibe-coded internal tools deployed in an operational setting
- An advanced degree (M.Ed., MBA, or doctorate)—common among candidates in this profile, though not required; no formal education is mandated for this role
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