Crossover · 4 hours ago
Regional Director of Family Engagement, Alpha - $200,000/year USD
Cook County, IL
Full-time
Onsite
Lead/Staff, Director/Executive
$200K/yr - $200K/yr
5+ years expCrossover is a technology startup aiming to transform education through AI-driven applications. The Regional Director of Family Engagement will manage the enrollment sales process, build relationships with affluent families, and advocate for the school's innovative educational model.
Information Technology & Services
No H1B
Responsibilities
Control enrollment sales during the 0-1 year phase, then transition to developing parent relationships that generate advocates and fuel referral-driven growth
Deliver information sessions and campus experiences that convert interested families while strategically declining misaligned applicants (selectivity is equally important as enrollment)
Function as the primary liaison for affluent families investing $40K+ per year, delivering concierge-level service that transforms parents into active promoters
Establish community presence through consistent on-campus availability during morning arrival (7-9am) and afternoon dismissal (2-4pm), while dedicating the majority of workdays to external relationship-building: coffee conversations, networking activities, and community alliances
Articulate and defend Alpha's AI-driven educational approach to parents who express concerns about technology use and unconventional pedagogy
Mobilize parent advocates by creating outstanding experiences that motivate families to recruit within their networks
Qualification
Required
Currently live within commuting range of one of these campuses OR prepared to relocate within 60 days (priority given to candidates with existing local ties): Santa Barbara, CA; Palo Alto, CA; Piedmont, CA; Roswell, GA; Chicago, IL; Bethesda, MD; Austin, TX; Brownsville, TX; Chantilly, VA; or Kirkland, WA
Authorized to work in the United States without requiring sponsorship
5+ years in positions involving high-net-worth client relationships within consultative sales or premium customer experience contexts (examples: private school admissions/enrollment, luxury retail, high-end hospitality, philanthropic development, etc.)
Proven enrollment or sales pipeline performance with quantifiable conversion results you can articulate
Professional presence and communication ability to establish credibility and influence complex decisions with affluent clientele
Self-directed entrepreneurial mindset with capability to function independently in startup conditions
Authentic belief in AI-enhanced education, with confidence addressing skeptical parents who question technology exposure and alternative educational models
Schedule flexibility for non-standard hours: early mornings (7-9am), late afternoons (2-4pm), evening programming (2-3x/month), and weekend events
Preferred
Established connections within the local affluent community with pre-existing relationships
Leadership experience in private or independent school enrollment/admissions with documented success
Sales, business development, or fundraising performance history with high-value clientele
Background in startup or early-stage ventures managing uncertainty and rapid evolution
Experience designing and executing events and community initiatives that create lasting impact
Background in real estate, development, or major donor fundraising involving ultra-high-net-worth individuals
Benefits
Relocation support is provided for candidates who have confirmed relocation plans and timelines.
This is a full-time (40 hours per week), long-term position.
Company
Crossover
Crossover is a global recruitment company, founded in 2014.
5001-10000 employees
Funding
Current Stage
Late StageLeadership Team
Brad Weinert
COO
Recent News
2025-04-12
Geeky Gadgets
2025-01-24
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