Director of Parent Engagement at Crossover

• Location: On-site at one of five California campuses—Palo Alto, Piedmont, San Francisco, La Jolla (San Diego), or Los Angeles (South Bay)
• Compensation: $200,000 annually
• Full-time
• Benefits include: Health, vision, dental, 401k, paid time off, and more

The families you serve don't require additional resources. What they need is someone they trust completely.

This position stands at the heart of that trust. You will be the individual families turn to when something doesn't feel right, when they seek counsel, or when they want to discuss what truly matters. Not because the title demands it—but because you have built that credibility. Your influence will define how families experience their child's education at one of Alpha's five California locations: Palo Alto, Piedmont, downtown San Francisco, La Jolla, or South Bay (Los Angeles).

Alpha is constructing a fundamentally different school model. Students finish core academics in two hours daily through AI-powered systems, then dedicate the remainder of their time to public speaking, critical thinking, and practical execution. No traditional lectures. No unnecessary assignments. Top 1% national performance. Our families are discerning, well-counseled, and frequently skeptical. They demand clear reasoning, not rehearsed responses.

You will steward that dialogue over the long term. Not simply during enrollment, but across years. You will speak with authority about AI—its mechanics, its shortcomings, and its significance—particularly with families who lead companies, fund them, or demand rigor in every choice. If you cannot sustain that caliber of dialogue, this role will prove challenging. If you can, it becomes among the most intellectually stimulating positions in education.

This is not client management. This is enduring trust with ultra-high-net-worth families who demand discretion, discernment, and reliability. If that context feels natural—and you rely on AI daily to accelerate your thinking, writing, and execution—you will see the opportunity instantly.

What You Will Be Doing

• Take full ownership of every family relationship on campus, cultivating trust that grows stronger with time
• Identify and address concerns proactively with discretion, efficiency, and solid judgment
• Be visibly present during critical touchpoints: morning arrivals, afternoon departures, and thoughtfully designed parent gatherings
• Facilitate continuous, substantive conversations about Alpha's AI-powered model with highly analytical, technology-oriented families
• Create and iterate on community experiences that foster belonging, advocacy, and organic referrals

What You Won’t Be Doing

• Overseeing admissions pipelines or enrollment metrics—your work starts after families enroll
• Working primarily from a desk or relying solely on email—this position requires significant in-person presence
• Using scripted answers or sidestepping difficult questions about AI or educational philosophy
• Depending on established procedures—you will create frameworks where none currently exist
• Viewing families as accounts—this role values judgment over task execution

Director Of Parent Engagement Key Responsibilities

Establish and maintain deep trust with ultra-high-net-worth families, securing sustained retention, advocacy, and confidence in Alpha's AI-driven educational approach.

Basic Requirements

• Located in or capable of daily commuting to Palo Alto, Piedmont, San Francisco, La Jolla, or Los Angeles
• 5+ years of direct experience working with UHNW individuals or families in settings such as private schools, private equity, family offices, or premium client service roles
• Demonstrated capacity to manage complex, high-stakes relationships with discretion and thoughtful judgment
• Daily, active use of AI tools (e.g., ChatGPT, Claude, Perplexity) with the capacity to articulate AI capabilities, risks, and boundaries clearly
• Commanding presence and communication approach that builds credibility with highly educated, demanding families
• Knowledge of private or independent school environments, gained professionally or personally
• Willingness to work early mornings, late afternoons, and occasional evening or weekend events

Nice-to-have Requirements

• Established connections within local private school or UHNW networks
• Background working with founders, investors, or technology executives
• Proven success in creating communities or experiences that generate natural referrals
• Experience in early-stage or rapidly scaling organizations where uncertainty is common
• Skill in translating sophisticated technical ideas into clear, assured dialogue

About Alpha

Want to join a learning rebellion that’s transforming the traditional classroom?

Alpha School is on a mission to reshape education with a bold approach that harnesses AI to accelerate learning and unleash student potential.

They don’t play by the old rules.

Alpha is creating a new paradigm where students master core academics in just two hours a day, freeing up time for hands-on, passion-driven learning that truly prepares them for the real world.

Alpha School is rewriting the rules of education.

Sounds too good to be true? It’s not.

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 (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5798-US-LakeFore-DirectorofPare.002