Vice President of Community Relations, 2 Hour Learning - $400,000/year USD

Your entry into private school leadership was driven by a desire to influence how children are educated—not to manage fundraising efforts or mediate parent committees. A version of this role exists where the academic framework is safeguarded centrally, operational functions are handled by dedicated teams, and your time is devoted to what you do exceptionally well: engaging the families who have the greatest impact, converting them into champions, and serving as the definitive voice when difficult conversations arise.

You will lead the parent-facing side of 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 commit, current UHNW families who re-enroll, refer others, and publicly endorse 2 Hour Learning, and a regional community in which Alpha maintains strong visibility. Approximately half your time will be externally focused—cultivating community partnerships, conducting information sessions, and holding one-on-one discussions with discerning parents who have engaged with every AI critique and expect to understand why this model delivers.

The remainder of your role serves as the escalation point. When an Associate Dean of Parents encounters a situation beyond their authority—a prominent family considering withdrawal, or a campus beginning to dilute the model to appease a vocal parent—you step in. You preserve both the family relationship and the integrity of the model. Then you create a documented precedent so the Associate Dean network can address similar issues independently in the future.

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

What You Will Be Doing

• Developing regional visibility by establishing partnerships with family offices, exclusive clubs, and independent advisors, along with hosting workshops and community gatherings that drive inbound interest
• Overseeing the complete admissions process for affluent families: information sessions, CRM-tracked individual follow-ups, and enrollment decisions, including communicating when a family is not a good fit for the school
• Cultivating enrolled parents as vocal advocates for 2 Hour Learning via advocacy workshops and parent-to-parent networks, transforming current families into your most effective source of new prospects
• Handling escalations that others are unable to resolve: determining whether the issue lies with the model, campus implementation, or family alignment, engaging directly with the family, and then documenting the resolution for use across the network
• Maintaining strong connections with current families through consistent engagement, and surfacing the trends you observe to leadership
  
  

What You Won’t Be Doing

• Leading capital campaigns, donor cultivation, major gift solicitation, or any other fundraising activities
• Organizing PTAs, School Improvement Councils, parent committees, or focus groups that hold decision-making authority over school policy
• Overseeing facilities, finance, legal, vendors, technology, marketing, or community logistics—these functions are centralized, ensuring your time remains focused on relationships rather than operations
• Creating curriculum or providing instructional coaching to staff; the academic model is maintained and protected by central leadership
• Approving exceptions or modifications to the educational model in response to parent requests, regardless of the parent's influence
• Merely logging and addressing complaints, or drafting newsletters and standard parent communications
• Resolving conflict through avoidance—diplomacy in this role requires delivering difficult messages and upholding standards
• Operating remotely; this is an on-site, full-time position representing the public face of the school, with evening and weekend community commitments
  
  

Vice President Of Community Relations Key Responsibilities

Establish a metropolitan region where Alpha families serve as 2 Hour Learning's most vocal supporters—and where no parent challenge is addressed by diluting the model.

Basic Requirements

• 7 years in a position centered on high-stakes relationship management: head of school, fundraising, enterprise sales, private wealth management, or client success
• Consistent, direct engagement with ultra-high-net-worth (UHNW) families, including households with $1M annual income 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 in UHNW client services
• At least one documented instance of personally guiding a sensitive matter to resolution: a parent crisis, a staff investigation, a media inquiry, or a regulatory interaction
• Demonstrated ability to uphold standards when faced with pressure from influential stakeholders
• Residence in the Miami, San Francisco, or Los Angeles metropolitan area, with availability to work on-site full-time, including evening and weekend events
• Authorization to work in the United States without requiring sponsorship
  
  

Nice-to-have Requirements

• Current or recent Head of School—or senior leadership partner—at a premier independent K-12 institution (NAIS-member or equivalent)
• Experience leading multi-campus or multi-site school operations (regional director, network superintendent, COO of a school network)
• UHNW client-services expertise applied to school leadership: private wealth management, single-family office, or major-gifts development at an elite preparatory school or Ivy League institution
• Established connections among UHNW families or prominent local organizations in Miami, San Francisco, or Los Angeles
• Background in crisis communication involving media, regulators, or board-level stakeholders
• Practical AI development experience—custom GPTs, agents, or internally developed 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 credential is 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. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time, W2 employee position with immediate access to benefits (https://support.crossover.com/article/7581-w2-benefits-u-s-paychex-paid-only). All roles are year-long positions. The compensation level for this role is $400,000 USD/year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5465-US-LasVegas-VicePresidento2