Jobs · Vermont

Client Success Director, Alpha - $200,000/year USD

Crossover · Vermont, United States · Yesterday
$200k/yrFull-time

About the role

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.

Responsibilities

  • Take ownership of the relationship with every family on campus—the continuous, evolving connection that ensures parents feel recognized, not merely attended to
  • Identify concerns ahead of their articulation and address them with the tact and interpersonal skill that preserves confidence
  • Maintain visible presence in the places families gather: morning arrival (7–9am), afternoon dismissal (2–4pm), evening parent programming, and select weekend engagements
  • Create a campus culture with authentic depth—programming, rituals, and moments that foster a sense of belonging to something families want to safeguard
  • Encourage parent champions naturally, creating consistently superior experiences that make referrals an organic result
  • Sustain the ongoing dialogue about Alpha's AI-driven approach with families managing concerns around screen exposure, skeptical relatives, and periodic uncertainty—not only during enrollment but across their entire campus tenure
  • Recognize when a family isn't aligned and manage that transition with the same composure you apply to all interactions—safeguarding the community is integral to serving it
  • Establish the structures and routines this position demands in a setting where the framework is still evolving

Requirements

  • Currently live within commuting range of one of these campuses OR willing to relocate within 60 days (preference given to candidates with established local ties)
  • Denver, CO; Greenwich, CT; Boca Raton, FL; Tampa, FL; Boston, MA; Bethesda, MD; Charlotte, NC; Las Vegas, NV; Oklahoma City, OK; Tulsa, OK; Nashville, TN; Austin, TX; Dallas (Carrollton), TX; Fort Worth, TX; Houston (The Woodlands), TX; Park City, UT; Burlington, VT; Kirkland, WA; or Jackson Hole, WY
  • Legally authorized for U.S. employment without sponsorship requirements
  • 5+ years in a client-facing role serving high-net-worth or ultra-high-net-worth families—private school administration, luxury hospitality, philanthropic advising, or any context where discretion, interpersonal warmth, and social sophistication were equally essential as competence
  • Proven capacity to maintain relationships through challenging situations with sophisticated families and conclude with trust strengthened
  • Authentic presence and communication approach that secures confidence rapidly with affluent, high-expectation families—polished without appearing rehearsed
  • Direct familiarity with independent, private, or alternative education—through professional experience or as a parent—that provides you credible perspective when families challenge the model
  • Authentic conviction in AI-enabled education and the capacity to sustain that belief genuinely across years of family interactions, not solely during initial enrollment
  • Flexibility for non-standard hours: early mornings (7–9am), late afternoons (2–4pm), evening programming 2–3x/month, and periodic weekend activities

Nice-to-have Requirements

  • Established connections within the local affluent community that would provide immediate, organic credibility on campus
  • Private or independent school background with demonstrated success in family retention and community building—beyond enrollment metrics alone
  • Experience managing high-stakes family dynamics where your discretion and judgment were the foundation of sustained trust
  • A talent for designing experiences—programming, occasions, environments—where participants feel part of something they want to protect
  • Prior startup or early-stage involvement where you built infrastructure from the ground up and remained steady through rapid change

About Alpha

Join the team building school around student growth Alpha reimagines the school day around faster learning, stronger mentorship, and more time for students to build real-world skills. Roles with real student impact: Alpha hires teachers (guides), operators, admissions experts, school & curriculum leaders, and remote team members. Education work that pays like it matters: Alpha offers six-figure roles for people ready to help build a radically better school experience. A culture built for builders: Alpha is fast-moving, ambitious, and student focused. It’s for people who want to improve the system, not maintain it. Alpha is where you can do the most meaningful work of your career. There is so much to cover for this exciting role, and space here is limited.

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