Demo

Director of Family Engagement, Alpha - $200,000/year USD

Crossover
Forest, CA Full Time
POSTED ON 5/18/2026
AVAILABLE BEFORE 8/10/2026
  • 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 package: Health, dental, vision, 401k, paid time off, and more

The families you'll serve don't need another vendor. They need someone they can trust completely.

This position exists at the heart of that trust. You'll become the individual families turn to when something doesn't feel right, when they're seeking clarity, or when they want to discuss what truly matters. Not as a function of title—but because you've genuinely earned their confidence. Your role will define how families experience their child's education at one of our five California locations: Palo Alto, Piedmont, downtown San Francisco, La Jolla, or South Bay Los Angeles.

Alpha represents a fundamentally different approach to schooling. Students complete their core academic work in just two hours daily through AI-powered learning systems, then dedicate the remainder of their day to public speaking, critical reasoning, and applied real-world skills. No traditional lectures. No filler assignments. Top 1% performance outcomes on a national scale. Our parent community is sophisticated, expertly advised, and often initially skeptical. They demand rigorous thinking, not rehearsed talking points.

You'll steward that dialogue continuously over time. Not merely during the enrollment phase, but throughout the years that follow. You'll speak with authority about artificial intelligence—its mechanics, its shortcomings, and its significance—particularly with families who launch companies, fund ventures, or demand exactness in every choice. If you're unable to engage at that caliber, this role will prove exhausting. If you can, it transforms into one of the most intellectually stimulating positions in the education sector.

This is not client account management. This is enduring trust-building with ultra-high-net-worth households who require discretion, judgment, and unwavering consistency. If that setting resonates with your background—and you leverage AI tools daily to accelerate your thinking, writing, and execution—the opportunity here will be immediately evident.

What You Will Be Doing

  • Take full ownership of relationships with every family at your campus, cultivating trust that strengthens over time
  • Identify and address concerns proactively, handling them with confidentiality, urgency, and mature judgment
  • Remain highly visible during critical touchpoints: morning arrival, afternoon dismissal, and thoughtfully curated family gatherings
  • Facilitate ongoing, substantive discussions about Alpha's AI-driven educational approach with analytical, technologically sophisticated families
  • Create and continuously improve community programming that fosters connection, active support, and organic referral growth

What You Won’t Be Doing

  • Overseeing admissions pipelines or enrollment quotas—your work starts once families have already committed
  • Operating primarily from behind a desk or through email correspondence—this is a highly visible, in-person position
  • Using scripted responses or avoiding challenging questions about artificial intelligence or educational philosophy
  • Depending on fixed, predefined procedures—you'll establish frameworks where none currently exist
  • Viewing families as transactional accounts—this role values discernment and relational intelligence over checklist execution

Director Of Family Engagement Key Responsibilities

Cultivate and maintain profound trust with ultra-high-net-worth families, driving sustained retention, enthusiastic advocacy, and enduring confidence in Alpha's AI-enabled educational approach.

Basic Requirements

  • Located in or capable of daily commuting to Palo Alto, Piedmont, San Francisco, La Jolla, or Los Angeles
  • Minimum 5 years of direct experience working with UHNW individuals or families in contexts such as private schools, private equity, family offices, or premium client service settings
  • Demonstrated capability to manage nuanced, high-stakes relationships with discretion and mature judgment
  • Daily, hands-on user of AI platforms (such as ChatGPT, Claude, Perplexity) with fluency in articulating AI functionality, risks, and boundaries
  • Commanding presence and communication approach that establishes credibility among highly educated, demanding families
  • Professional or personal familiarity with private or independent school environments
  • Flexibility for early morning, late afternoon, and occasional evening or weekend programming

Nice-to-have Requirements

  • Established connections within local private school networks or UHNW circles
  • Background working alongside founders, venture investors, or technology executives
  • History of developing community initiatives or experiences that generate word-of-mouth referrals
  • Prior exposure to early-stage or rapidly scaling organizations where structure is still emerging
  • Skill in distilling 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-DirectorofFami

Salary : $200,000

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