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

You chose private school leadership because you wanted to influence how students are educated—not to manage fundraising drives or mediate parent councils. This role offers a different model: the academic program is centrally protected, operational demands are managed by shared services, and your focus is what you do exceptionally well: building trust with the families who define your success, converting them into vocal supporters, and serving as the decisive voice when difficult conversations arise. You will lead parent engagement for Alpha in a single metropolitan area—Miami, San Francisco, or Los Angeles. Success will be measured by enrollment and advocacy: prospective ultra-high-net-worth 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 who have studied AI critiques and want to understand why this educational approach is sound. The other half of your role is escalation management. When an Associate Dean of Parents encounters a situation beyond their authority—a high-profile family threatening withdrawal, or a campus beginning to dilute the model to appease a demanding parent—the matter escalates to you. Your task is to retain the family while preserving the integrity of the model. Both outcomes are required. You then document the resolution so the Associate Dean network can manage similar cases independently going forward. If you have led a private or independent K-12 school, or if you have built a career earning the confidence of UHNW families in another sector, and you have been seeking a position where sound judgment and effective persuasion are the core work product, this role is that opportunity. What You Will Be Doing Establishing local visibility by forming relationships with family offices, private membership organizations, and independent advisors, and hosting workshops and community programming that drive inbound interest Managing the full admissions cycle for affluent families: leading information sessions, conducting 1:1 follow-ups documented in the CRM, and making enrollment decisions, including informing families when the school is not the appropriate match for their child Converting enrolled parents into vocal advocates for 2 Hour Learning by facilitating advocacy workshops and peer networks, ensuring that current families become your most effective channel for new inquiries Handling escalations that exceed the capacity of frontline staff: determining whether the issue stems from the model itself, campus implementation, or family alignment, engaging directly with the family, and then creating a written precedent for network-wide reference Maintaining regular contact with current families through consistent touchpoints, and surfacing 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 so your time remains dedicated to relationship management 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 in this context 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 Director Of School Development Key Responsibilities Create 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 educational model. Basic 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; no formal educational credentials are required for this position 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, it’s talent and performance that 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. 2 Hour Learning is reprogramming learning for the AI era Here’s How They’re Fixing It There is so much to cover for this exciting role, and space here is limited. Working with us This is a full-time, W2 employee position with immediate access to benefits ( All roles are year-long positions. The compensation level for this role is $400,000 USD/year. The payment period is weekly. 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