Director of Parent 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 

Multiple Locations, US
Semi-flexible schedule
In-person
full-time (40 hrs/week)
Long-term role

Director of Parent Engagement   $400,000 USD/year

Description

You entered private school leadership to influence how students develop, not to manage fundraising drives or mediate parent governance structures. A version of this role exists where the educational framework is safeguarded on your behalf, operational functions are centrally managed, and your time is devoted to what you do best: securing the confidence of the most influential families, transforming them into champions, and serving as the definitive voice when discussions become difficult.

You will lead the parent dimension of Alpha within a single metropolitan area — Miami, San Francisco, or Los Angeles. Success is measured by enrollment and advocacy: prospective ultra-high-net-worth families who commit, existing UHNW families who remain, refer others, and publicly endorse 2 Hour Learning, and a regional presence where Alpha is consistently top of mind. Approximately half your time will be externally focused — forging community alliances, leading information sessions, and engaging in one-on-one dialogue with discerning parents who have studied every AI critique and want to understand why this model delivers results.

The other half of this position serves as the escalation channel. When an Associate Dean of Parents encounters a situation beyond their resolution capacity — a prominent family threatening withdrawal, a campus subtly diluting the model to appease a persistent parent — it escalates to you. You preserve both the family relationship and the integrity of the model. Then you codify the resolution so the Associate Dean network can manage similar cases independently going forward.

If you have led a private or independent K-12 institution, or you have built a career earning the confidence of UHNW families in another sector, and you have been seeking the position where sound judgment and persuasive communication are the core outputs, this is that role.

What you will be doing

  • Cultivating local visibility by establishing partnerships with family offices, private membership organizations, and independent advisors, alongside hosting workshops and community gatherings that drive inbound interest
  • Managing the full admissions cycle for affluent families: conducting information sessions, maintaining 1:1 follow-through in the CRM, and making enrollment decisions, which includes advising a family when this 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 most effective source of new inquiries
  • Addressing escalations beyond the capacity of others: determining whether the issue stems from the model, campus implementation, or family alignment, engaging directly with the family, then documenting the resolution as precedent for the broader network
  • Maintaining consistent engagement with current families through regular touchpoints, and communicating the trends you observe back to leadership

What you will NOT be doing

  • Leading capital campaigns, donor cultivation efforts, major gift initiatives, or any other fundraising activities
  • Organizing PTAs, School Improvement Councils, parent committees, or focus groups that hold decision-making authority over school policies
  • Overseeing facilities, finance, legal matters, vendor relationships, technology, marketing, or community logistics — all centralized teams handle these functions, allowing your time to remain focused on relationships rather than operations
  • Developing curriculum or providing instructional coaching to teaching staff on pedagogy; the academic framework is centrally owned and protected
  • Granting exceptions or modifications to the educational model in response to parent requests, regardless of the parent's influence
  • Merely logging and replying to complaints, or drafting newsletters and routine parent correspondence
  • Resolving conflict through avoidance — diplomacy in this context means communicating difficult truths, not compromising standards
  • Operating remotely; this is an on-site, full-time, public-facing position that requires participation in evening and weekend community events

Key responsibilities

Develop a metropolitan area where Alpha families serve as 2 Hour Learning's most vocal advocates — and where every parent challenge is resolved without compromising the integrity of the model.

Candidate requirements

  • 7+ years in a position centered on high-stakes relationship management: head of school, fundraising leadership, enterprise sales, private wealth management, or client success
  • Sustained, direct engagement with ultra-high-net-worth (UHNW) families, including households with annual incomes of $1M+ or families paying full tuition at elite private schools
  • Background 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 instance of personally guiding a sensitive situation to resolution: a parent crisis, a staff investigation, a media inquiry, or a regulatory engagement
  • Demonstrated history of upholding a standard when influential stakeholders challenge it
  • Current residence in the Miami, San Francisco, or Los Angeles metropolitan area, with availability to work on-site full-time, including evenings and weekends
  • Authorization to work in the United States without sponsorship

Nice to have

  • Current or recent Head of School — or senior leadership partner to the Head — at a top-tier independent K-12 institution (NAIS-member or equivalent caliber)
  • Leadership experience across multiple campuses or sites (regional director, network superintendent, COO within a school network)
  • UHNW client-services expertise transitioned into educational leadership: private wealth management, single-family office operations, or major-gifts development at an elite preparatory school or Ivy League institution
  • Established connections among UHNW families or influential local institutions in Miami, San Francisco, or Los Angeles
  • Crisis communication experience involving media, regulatory bodies, or board-level stakeholders
  • Practical AI development experience — custom GPTs, agents, or internally built tools applied in a real operational setting
  • An advanced degree (M.Ed., MBA, or doctorate) — typical for this profile, though not mandatory; no formal education credentials are required for this position

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