Director of School Development, 2 Hour Learning - $400,000/year USD

About the role

This role offers a different model: the academic program is centrally protected, operational demands are managed by shared services, and your focus is building trust with ultra-high-net-worth (UHNW) families—converting them into vocal supporters and serving as the decisive voice in difficult conversations. You will lead parent engagement for Alpha in a single metropolitan area—Miami, San Francisco, or Los Angeles. Success is measured by enrollment and advocacy: prospective UHNW families who enroll, current families who renew, refer peers, and become public advocates for 2 Hour Learning, and a regional presence where Alpha is consistently recognized.

Approximately half your time will be externally focused—building community partnerships, hosting information sessions, and engaging in one-on-one dialogues with discerning parents. The other half involves escalation management: resolving high-stakes situations (e.g., a family threatening withdrawal or a campus diluting the model) while preserving the integrity of the program. Resolutions are documented to build precedent for the Associate Dean network.

Responsibilities

• Establish local visibility by forming relationships with family offices, private membership organizations, and independent advisors, and hosting workshops and community programming that drive inbound interest.
• Manage the full admissions cycle for affluent families: lead information sessions, conduct 1:1 follow-ups documented in the CRM, and make enrollment decisions, including informing families when the school is not the right match.
• Convert enrolled parents into vocal advocates for 2 Hour Learning by facilitating advocacy workshops and peer networks, ensuring current families become your most effective channel for new inquiries.
• Handle escalations that exceed frontline staff capacity: determine whether issues stem from the model, campus implementation, or family alignment; engage directly with families; and create written precedents for network-wide reference.
• Maintain regular contact with current families through consistent touchpoints and surface recurring themes to leadership.

What You Won’t Be Doing

• Leading capital campaigns, cultivating donors, securing major gifts, or engaging in fundraising.
• Organizing PTAs, School Improvement Councils, parent committees, or focus groups that influence school policy.
• Overseeing facilities, finance, legal matters, vendor relationships, technology infrastructure, marketing, or community logistics (centralized teams handle these).
• Developing curriculum or providing instructional coaching (the academic model is centrally owned).
• Granting exceptions or bespoke modifications to the educational approach to accommodate parent requests, regardless of influence.
• Merely logging complaints, drafting responses, or producing routine parent updates.
• Resolving conflict through avoidance—effective diplomacy requires delivering difficult messages and upholding standards.
• Operating remotely; this is an on-site, full-time position as the public face of the school, including evening and weekend obligations.

Requirements

• 7+ years in high-stakes relationship management: head of school, development, enterprise sales, private wealth advisory, or client success.
• Documented, sustained engagement with UHNW families (households with annual income of $1M+ or families paying full tuition at elite private institutions).
• Background in parent-facing or client-facing roles at an independent or private K-12 school, or in UHNW client services.
• At least one documented instance of personally guiding a sensitive matter to resolution (e.g., parent crisis, staff investigation, media inquiry, or regulatory engagement).
• Demonstrated ability to uphold standards under pressure from influential stakeholders.
• Current residence in Miami, San Francisco, or Los Angeles metropolitan area, with availability for on-site, full-time work (including evenings/weekends).
• Authorization to work in the U.S. without sponsorship.

Nice-to-have Qualifications

• Current or recent Head of School—or senior deputy—at a top-tier independent K-12 institution (NAIS-affiliated or equivalent).
• Leadership experience across multiple campuses (regional director, network superintendent, or COO within a school network).
• UHNW client-services expertise applied to education: private wealth management, single-family office operations, or major-gifts fundraising at elite preparatory schools or Ivy League institutions.
• Established connections among UHNW families or prominent local institutions in Miami, San Francisco, or Los Angeles.
• Crisis communications experience involving media relations, regulatory bodies, or board-level constituents.
• Practical AI development experience (e.g., building custom GPTs, agents, or internally deployed tools).
• Graduate-level education (M.Ed., MBA, or doctorate)—common but not required.

About 2 Hour Learning

2 Hour Learning is transforming education by replacing the outdated one-size-fits-all model with AI-driven personalized learning. Students master academics in just two hours a day, consistently ranking in the top 1-2% nationally, with the top 20% achieving 6.5x growth. The organization prioritizes talent and performance, offering a dynamic environment for innovators, educators, and AI specialists to fix a broken school system.

Benefits

This is a full-time, W2 employee position with immediate access to benefits. All roles are year-long positions.

Pay

The compensation for this role is $400,000 USD per year, paid weekly.

Schedule

Full-time, on-site position requiring participation in evening and weekend community programming.