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 who define your success. 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 UHNW 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: when an Associate Dean of Parents encounters a situation beyond their authority, the matter escalates to you. Your task is to retain the family while preserving the integrity of the model, then document the resolution for network-wide reference.

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 appropriate match for their child
• 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 the capacity of frontline staff: determine whether the issue stems from the model, campus implementation, or family alignment, engage directly with the family, and create a written precedent 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 any fundraising activities
• Organizing PTAs, School Improvement Councils, parent committees, or focus groups that influence school policy through voting mechanisms
• Overseeing facilities, finance, legal matters, vendor relationships, technology infrastructure, marketing, or community logistics—centralized teams manage all operational functions
• Developing curriculum or providing instructional coaching to teaching staff; the academic model is centrally owned and safeguarded
• Granting exceptions or bespoke modifications to the educational approach to accommodate parent requests, regardless of the parent's influence
• Merely logging complaints and drafting responses, or producing newsletters and 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 participation in evening and weekend community programming

Requirements

• 7+ years in a position centered on high-stakes relationship management: head of school, development, enterprise sales, private wealth advisory, or client success
• Documented, sustained engagement with ultra-high-net-worth (UHNW) families, defined as households with annual income of $1M+ or families paying full tuition at elite private institutions
• Background in a parent-facing or client-facing capacity 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 successful resolution: a parent crisis, staff investigation, media inquiry, or regulatory engagement
• Demonstrated ability to uphold standards in the face of pressure from influential stakeholders
• Current residence in the Miami, San Francisco, or Los Angeles metropolitan area, with availability to work on-site full-time, including evening and weekend obligations
• Authorization to work in the United States without requiring sponsorship

Nice-to-have Requirements

• Current or recent Head of School—or senior deputy to the Head—at a top-tier independent K-12 institution (NAIS-affiliated or equivalent caliber)
• Leadership experience across multiple campuses or sites (regional director, network superintendent, or COO within a school network)
• UHNW client-services expertise applied to educational leadership: 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—building custom GPTs, agents, or internally deployed tools used in operational settings
• Graduate-level education (M.Ed., MBA, or doctorate)—common among candidates in this profile, though not mandatory

About 2 Hour Learning

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, talent and performance 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.

Benefits

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

Pay

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