Crossover
Director of Parent Engagement & Advocacy, Alpha - $200,000/year USD
Crossover, Washington, District Of Columbia, United States
Overview
LOCATION NOTE: This position requires on-site work in one of the cities listed below, with local travel as required. We offer relocation assistance to candidates who present concrete relocation plans and timelines.
You excel in the unpredictability of startup environments. You have a proven track record working with high-net-worth clients who demand exceptional service. You hold a genuine conviction that AI can transform education and welcome the opportunity to defend that position against skeptics. If these conditions create discomfort, this position is not the right fit.
Alpha operates outside the traditional school model. We are a technology startup demonstrating that every child possesses exceptional potential. Our students complete their core academic requirements in just two hours daily through AI-driven applications, dedicating remaining time to practical competencies: public speaking, critical thinking, collaborative challenges, and meaningful projects. No lectures. No redundant assignments. Only accelerated learning delivering top 1% outcomes nationally. Parents anticipate concierge-tier service. You will continuously defend this approach against concerns about screen time, skepticism from traditional education advocates, and "this seems unrealistic" objections.
During year zero through year one, this functions as an enrollment sales position. You control the complete pipeline from initial inquiry through executed enrollment agreements, accountable for conversion metrics and CRM oversight. We will not launch a campus with fewer than 25 enrolled students. Achieving that threshold is your responsibility. You will facilitate compelling information sessions, execute individual campus tours, maintain persistent follow-up, and finalize agreements. After reaching 25 students and onboarding an admissions director, your role transitions to serving as the campus's principal parent-facing leader. You will cultivate loyalty, address concerns with white-glove attention, and transform satisfied parents into vocal advocates who actively recruit others.
This position offers high trust and autonomy with explicit accountability. You will operate independently without substantial administrative infrastructure, marketing resources, or established protocols. Strategy evolves based on performance data. Systems are under development. You will create them. You will spend the majority of your time in the community (coffee conversations, networking lunches, Chamber of Commerce participation) rather than at a desk. You will maintain visibility during morning arrival and afternoon departure times. You will participate in evening parent gatherings and occasional weekend student programming. A single poorly-aligned family within a 25-student cohort can compromise everything, making the ability to decline wrong-fit families as critical as enrolling appropriate ones.
The opportunity? You will observe transformations rarely witnessed by educators: skeptical parents evolving into passionate advocates, reserved students presenting with confidence to adult audiences, families selecting your campus over prestigious private institutions. You will create something substantial from the ground up and own the outcomes.
If you believe the current education system is failing children and a superior alternative exists, this represents your opportunity to demonstrate it.
Hiring Locations
CA: Santa Barbara, Palo Alto, & Piedmont (East Bay)
GA: Roswell (Atlanta)
IL: Chicago
MD: Bethesda
TX: Austin & Brownsville
VA: Chantilly
WA: Kirkland (Seattle)
What You Will Be Doing
Control the complete enrollment sales pipeline during year 0-1, spanning inquiry through executed agreements, managing conversion targets and CRM systems until the 25-student threshold is achieved
Facilitate information sessions and campus tours that convert interested parents while strategically declining wrong-fit families (selective rejection is as critical as acceptance)
Function as the principal contact for high-net-worth families investing $40K+ annually, delivering white-glove service that converts parents into advocates
Establish visibility through consistent on-site presence during morning arrival (7-9am) and afternoon departure (2-4pm), while dedicating most working hours to community engagement through coffee meetings, networking activities, and partnership development
Advocate for Alpha's AI-driven model when addressing skeptical parents who raise concerns about screen time and non-traditional education approaches
Mobilize parent champions by creating exceptional experiences that motivate families to actively recruit their networks
What You Won’t Be Doing
Maintaining standard 9-5 schedules (early mornings, extended afternoons, and evening commitments are necessary)
Implementing pre-existing playbooks and standardized procedures (you will build systems within a startup context)
Depending on administrative personnel, marketing departments, or enrollment support teams (you operate independently)
Enrolling every applicant family (strategic selectivity is a fundamental competency)
Working primarily from a desk (this position demands daily community engagement and active relationship cultivation)
Director Of Parent Engagement & Advocacy Key Responsibilities Control enrollment sales during year 0-1, subsequently transitioning to cultivating parent relationships that generate advocates and fuel word-of-mouth expansion.
Basic Requirements
Currently reside within commuting distance of one of these campuses OR willing to relocate within 60 days (preference for existing local connections): Santa Barbara, CA; Palo Alto, CA; Piedmont, CA; Roswell, GA; Chicago, IL; Bethesda, MD; Austin, TX; Brownsville, TX; Chantilly, VA; or Kirkland, WA.
Legally authorized to work in the U.S. without sponsorship
5+ years in positions involving work with high-net worth clients through consultative sales or high-touch customer experience roles (examples: private school enrollment/admissions, luxury sales, hospitality, philanthropy, etc.)
Documented enrollment/sales funnel achievements with conversion metrics available for discussion
Executive presence and communication capabilities to establish trust and facilitate sophisticated decision-making with affluent families
Entrepreneurial self-starter comfortable operating independently within a startup environment
Authentic enthusiasm for AI-driven education, with confidence defending the model to skeptical parents questioning screen time and non-traditional methodologies
Availability for flexible scheduling: early mornings (7-9am), late afternoons (2-4pm), evening programming (2-3x/month), and weekend activities
Nice-to-have Requirements Exceptional candidates will possess at least one of the following:
Established network within the local affluent community with existing relationships
Private school or independent school enrollment/admissions leadership background with documented results
Sales, business development, or fundraising track record involving high-value clients
Prior startup or early-stage organization experience managing ambiguity and accelerated change
Event planning and community organizing background producing memorable experiences
Real estate, development, or major gift fundraising experience engaging with UHNW individuals
About Alpha 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-5598-US-Washingt-DirectorofPare3.014
#J-18808-Ljbffr
You excel in the unpredictability of startup environments. You have a proven track record working with high-net-worth clients who demand exceptional service. You hold a genuine conviction that AI can transform education and welcome the opportunity to defend that position against skeptics. If these conditions create discomfort, this position is not the right fit.
Alpha operates outside the traditional school model. We are a technology startup demonstrating that every child possesses exceptional potential. Our students complete their core academic requirements in just two hours daily through AI-driven applications, dedicating remaining time to practical competencies: public speaking, critical thinking, collaborative challenges, and meaningful projects. No lectures. No redundant assignments. Only accelerated learning delivering top 1% outcomes nationally. Parents anticipate concierge-tier service. You will continuously defend this approach against concerns about screen time, skepticism from traditional education advocates, and "this seems unrealistic" objections.
During year zero through year one, this functions as an enrollment sales position. You control the complete pipeline from initial inquiry through executed enrollment agreements, accountable for conversion metrics and CRM oversight. We will not launch a campus with fewer than 25 enrolled students. Achieving that threshold is your responsibility. You will facilitate compelling information sessions, execute individual campus tours, maintain persistent follow-up, and finalize agreements. After reaching 25 students and onboarding an admissions director, your role transitions to serving as the campus's principal parent-facing leader. You will cultivate loyalty, address concerns with white-glove attention, and transform satisfied parents into vocal advocates who actively recruit others.
This position offers high trust and autonomy with explicit accountability. You will operate independently without substantial administrative infrastructure, marketing resources, or established protocols. Strategy evolves based on performance data. Systems are under development. You will create them. You will spend the majority of your time in the community (coffee conversations, networking lunches, Chamber of Commerce participation) rather than at a desk. You will maintain visibility during morning arrival and afternoon departure times. You will participate in evening parent gatherings and occasional weekend student programming. A single poorly-aligned family within a 25-student cohort can compromise everything, making the ability to decline wrong-fit families as critical as enrolling appropriate ones.
The opportunity? You will observe transformations rarely witnessed by educators: skeptical parents evolving into passionate advocates, reserved students presenting with confidence to adult audiences, families selecting your campus over prestigious private institutions. You will create something substantial from the ground up and own the outcomes.
If you believe the current education system is failing children and a superior alternative exists, this represents your opportunity to demonstrate it.
Hiring Locations
CA: Santa Barbara, Palo Alto, & Piedmont (East Bay)
GA: Roswell (Atlanta)
IL: Chicago
MD: Bethesda
TX: Austin & Brownsville
VA: Chantilly
WA: Kirkland (Seattle)
What You Will Be Doing
Control the complete enrollment sales pipeline during year 0-1, spanning inquiry through executed agreements, managing conversion targets and CRM systems until the 25-student threshold is achieved
Facilitate information sessions and campus tours that convert interested parents while strategically declining wrong-fit families (selective rejection is as critical as acceptance)
Function as the principal contact for high-net-worth families investing $40K+ annually, delivering white-glove service that converts parents into advocates
Establish visibility through consistent on-site presence during morning arrival (7-9am) and afternoon departure (2-4pm), while dedicating most working hours to community engagement through coffee meetings, networking activities, and partnership development
Advocate for Alpha's AI-driven model when addressing skeptical parents who raise concerns about screen time and non-traditional education approaches
Mobilize parent champions by creating exceptional experiences that motivate families to actively recruit their networks
What You Won’t Be Doing
Maintaining standard 9-5 schedules (early mornings, extended afternoons, and evening commitments are necessary)
Implementing pre-existing playbooks and standardized procedures (you will build systems within a startup context)
Depending on administrative personnel, marketing departments, or enrollment support teams (you operate independently)
Enrolling every applicant family (strategic selectivity is a fundamental competency)
Working primarily from a desk (this position demands daily community engagement and active relationship cultivation)
Director Of Parent Engagement & Advocacy Key Responsibilities Control enrollment sales during year 0-1, subsequently transitioning to cultivating parent relationships that generate advocates and fuel word-of-mouth expansion.
Basic Requirements
Currently reside within commuting distance of one of these campuses OR willing to relocate within 60 days (preference for existing local connections): Santa Barbara, CA; Palo Alto, CA; Piedmont, CA; Roswell, GA; Chicago, IL; Bethesda, MD; Austin, TX; Brownsville, TX; Chantilly, VA; or Kirkland, WA.
Legally authorized to work in the U.S. without sponsorship
5+ years in positions involving work with high-net worth clients through consultative sales or high-touch customer experience roles (examples: private school enrollment/admissions, luxury sales, hospitality, philanthropy, etc.)
Documented enrollment/sales funnel achievements with conversion metrics available for discussion
Executive presence and communication capabilities to establish trust and facilitate sophisticated decision-making with affluent families
Entrepreneurial self-starter comfortable operating independently within a startup environment
Authentic enthusiasm for AI-driven education, with confidence defending the model to skeptical parents questioning screen time and non-traditional methodologies
Availability for flexible scheduling: early mornings (7-9am), late afternoons (2-4pm), evening programming (2-3x/month), and weekend activities
Nice-to-have Requirements Exceptional candidates will possess at least one of the following:
Established network within the local affluent community with existing relationships
Private school or independent school enrollment/admissions leadership background with documented results
Sales, business development, or fundraising track record involving high-value clients
Prior startup or early-stage organization experience managing ambiguity and accelerated change
Event planning and community organizing background producing memorable experiences
Real estate, development, or major gift fundraising experience engaging with UHNW individuals
About Alpha 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-5598-US-Washingt-DirectorofPare3.014
#J-18808-Ljbffr