
Director of Strategic Parent Engagement, Alpha - $200,000/year USD
Crossover, New York, NY, United States
You flourish in the unpredictability of startup environments. You've built strong relationships with affluent clients accustomed to premium service. You're convinced that AI will transform education and enjoy advocating that vision against critics. If these conditions make you uneasy, this position won't suit you.
Alpha operates differently from conventional schools. We're a technology startup demonstrating that every child possesses exceptional potential. Our students complete their core curriculum in two hours daily through AI-enabled applications, dedicating remaining time to practical competencies: presenting, reasoning, collaborative problem‑solving, and meaningful project work. We eliminate lectures and repetitive assignments, delivering accelerated progress and performance in the nation's top percentile. Families anticipate personalized, high‑touch service. You'll continuously articulate this approach in response to concerns about digital exposure, conventional education advocates, and skepticism that our outcomes seem implausible.
During the initial zero‑to‑one phase, this functions as an enrollment sales position. You control the entire pipeline from initial contact through executed enrollment contracts, meeting conversion benchmarks and maintaining CRM discipline. We require a minimum of 25 enrolled students before launching a campus. Achieving that threshold falls to you. You'll deliver compelling information sessions, facilitate individual campus visits, maintain persistent follow‑through, and secure commitments. After reaching 25 enrollments and an admissions director comes aboard, your responsibilities transition to serving as the campus's lead parent relationship manager. You'll cultivate loyalty, address concerns through premium service delivery, and convert satisfied families into vocal advocates who drive organic recruitment.
This position combines high trust and high autonomy with transparent accountability. You'll operate independently without substantial administrative infrastructure, marketing resources, or established protocols. Strategy adapts according to performance data. Systems are emerging. You'll create them. Your daily schedule emphasizes external engagement—coffee conversations, business lunches, Chamber involvement—rather than office‑based work. You'll maintain visibility at morning arrival and afternoon departure times. Evening parent programs and periodic weekend student events are expected. In a cohort of 25, a single poorly‑matched family can disrupt the entire community, making the ability to decline unsuitable applicants as critical as enrolling appropriate ones.
The upside? You'll observe transformations rarely seen in traditional education: doubtful parents evolving into passionate supporters, reserved students delivering poised presentations, families selecting your campus over established private institutions. You'll construct something from inception and claim ownership of outcomes.
If you're convinced that conventional schooling fails most children and a superior alternative exists, this represents your opportunity to demonstrate it.
Campus Locations Under Recruitment
- CA: Santa Barbara, Palo Alto, Piedmont (East Bay), & Lake Forest (Orange Co.)
- MD: Bethesda
- TX: Austin, Fort Worth (DFW)
- WA: Kirkland (Seattle)
This position requires on‑site presence in the cities specified above, including local travel. Relocation support is provided for candidates with confirmed relocation commitments and schedules.
What You Will Be Doing
- Manage the complete enrollment sales process during year 0‑1, spanning inquiry through executed agreement, meeting conversion objectives and maintaining CRM discipline until the 25‑student threshold is achieved.
- Deliver information sessions and campus visits that persuade qualified families while strategically declining poor‑fit applicants (rejection decisions carry equal weight to acceptances).
- Function as the principal liaison for affluent families investing $40K+ annually, delivering premium service that transforms parents into advocates.
- Establish community presence through consistent on‑site availability during morning arrival (7‑9 am) and afternoon departure (2‑4 pm), while dedicating most working hours to external relationship‑building through coffee meetings, networking, and community alliances.
- Articulate and justify Alpha's AI‑driven approach to questioning parents concerned about screen exposure and alternative education models.
- Mobilize parent ambassadors by creating exceptional experiences that motivate families to recruit within their networks.
What You Won’t Be Doing
- Maintaining standard 9‑5 schedules (early morning presence, late afternoon availability, and evening programming are essential).
- Executing established protocols and documented procedures (you’ll construct systems within a startup context).
- Depending on administrative personnel, marketing departments, or enrollment infrastructure (you operate independently).
- Enrolling every applicant (selective admissions represent a core capability).
- Working primarily from an office (this role demands daily community engagement and network cultivation).
Director Of Strategic Parent Engagement Key Responsibilities
Control enrollment sales during year 0‑1, then transition to cultivating parent relationships that generate advocates and fuel word‑of‑mouth expansion.
Basic Requirements
- Currently located within commuting range of one of these campuses OR committed to relocating within 60 days (local community ties preferred): Santa Barbara, CA; Palo Alto, CA; Piedmont, CA; Lake Forest, CA; Bethesda, MD; Austin, TX; Fort Worth, TX; or Kirkland, WA.
- Work authorization in the U.S. without sponsorship requirements.
- 5+ years in positions involving affluent client relationships through consultative sales or premium customer experience delivery (including private school enrollment/admissions, luxury goods sales, high‑end hospitality, philanthropic development, etc.).
- Documented enrollment/sales pipeline achievement with conversion performance you can articulate.
- Professional presence and communication capability to establish credibility and influence sophisticated decisions with high‑net‑worth families.
- Entrepreneurial initiative suited to independent operation within a startup context.
- Authentic belief in AI‑enabled education, with confidence defending the model against parents questioning screen exposure and non‑traditional methods.
- Schedule flexibility for early mornings (7‑9 am), late afternoons (2‑4 pm), evening programs (2‑3x monthly), and weekend activities.
Nice‑to‑have Requirements
Outstanding candidates will demonstrate at least one of the following:
- Pre‑existing relationships within the local affluent community with developed networks.
- Private school or independent school enrollment/admissions leadership with documented success.
- Sales, business development, or fundraising performance with high‑value client portfolios.
- Prior startup or early‑stage organization experience managing ambiguity and accelerated evolution.
- Event coordination and community programming expertise producing impactful experiences.
- Real estate, development, or major gift fundraising background engaging ultra‑high‑net‑worth individuals.
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 for more details on this topic.
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