Most enrollment positions prioritize throughput. This one is designed to uphold standards.
Alpha is developing one of the most forward-thinking school models globally. Our campuses integrate demanding academics, technology-enabled learning, and elevated expectations for both students and faculty. Students routinely exceed national learning benchmarks, supported by measurable evidence. Afternoon hours are dedicated to depth, autonomy, and practical competency development. The model delivers results—but only when paired with the right families.
This is your mandate.
You will control the entire enrollment experience for a campus, beginning with initial inquiry and concluding with onboarding. This is not a relay role. You determine how families perceive us, how thoroughly they grasp the model, and whether enrollment decisions reflect genuine alignment. You will evaluate compatibility, facilitate informed discussions, and advocate for rejection when circumstances warrant it. The objective is not enrollment maximization. The objective is fit.
We welcome candidates from elevated service sectors outside conventional education: independent schools, competitive programs, luxury hospitality, executive client services, premium membership platforms, or entrepreneurial leaders who have directly overseen high-value client relationships from start to finish. What counts is your capacity to orchestrate a sophisticated, multi-phase process with discernment, precision, and accountability.
If your professional background centers on delivering exceptional service where credibility, confidentiality, and experience integrity define brand identity, this role will resonate—simply applied to work that measurably transforms outcomes.
This is a full-time, salaried, on-site position. We are currently hiring across Santa Barbara, Santa Monica, Orange County, Roswell, Chicago, Charlotte, Raleigh, and Dallas-Fort Worth. Relocation assistance is provided.
What You Will Be Doing
Direct and deliver a high-trust, selective enrollment process that successfully onboards aligned families while safeguarding the integrity and academic performance of the Alpha model.
Basic Requirements
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-5531-US-Chicago-HeadofEnrollme
Alpha is developing one of the most forward-thinking school models globally. Our campuses integrate demanding academics, technology-enabled learning, and elevated expectations for both students and faculty. Students routinely exceed national learning benchmarks, supported by measurable evidence. Afternoon hours are dedicated to depth, autonomy, and practical competency development. The model delivers results—but only when paired with the right families.
This is your mandate.
You will control the entire enrollment experience for a campus, beginning with initial inquiry and concluding with onboarding. This is not a relay role. You determine how families perceive us, how thoroughly they grasp the model, and whether enrollment decisions reflect genuine alignment. You will evaluate compatibility, facilitate informed discussions, and advocate for rejection when circumstances warrant it. The objective is not enrollment maximization. The objective is fit.
We welcome candidates from elevated service sectors outside conventional education: independent schools, competitive programs, luxury hospitality, executive client services, premium membership platforms, or entrepreneurial leaders who have directly overseen high-value client relationships from start to finish. What counts is your capacity to orchestrate a sophisticated, multi-phase process with discernment, precision, and accountability.
If your professional background centers on delivering exceptional service where credibility, confidentiality, and experience integrity define brand identity, this role will resonate—simply applied to work that measurably transforms outcomes.
This is a full-time, salaried, on-site position. We are currently hiring across Santa Barbara, Santa Monica, Orange County, Roswell, Chicago, Charlotte, Raleigh, and Dallas-Fort Worth. Relocation assistance is provided.
What You Will Be Doing
- Controlling the complete enrollment pathway for prospective families, from initial outreach through final onboarding.
- Facilitating fit-assessment dialogues to establish compatibility before proposing solutions or advising subsequent actions.
- Overseeing 20+ concurrent family engagements across various enrollment phases, maintaining transparent status tracking and timely follow-up.
- Directing campus visits, shadow day experiences, and decision-stage discussions that transparently convey outcomes, expectations, and target audience.
- Sustaining precise CRM and enrollment documentation (HubSpot and SIS) to enable accurate forecasting, priority management, and service excellence.
- Deploying transactional or aggressive sales methods.
- Accepting families with poor alignment solely to achieve enrollment targets.
- Supervising large teams or navigating complex approval hierarchies.
- Distributing family experience ownership across multiple functions.
- Operating remotely. This position is intentionally campus-based.
Direct and deliver a high-trust, selective enrollment process that successfully onboards aligned families while safeguarding the integrity and academic performance of the Alpha model.
Basic Requirements
- 3+ years providing premium, individualized service in settings where service excellence directly influences brand standing (education, luxury hospitality, executive assistance, premium membership, or independently operated client services).
- Proven ownership of a complete client, admissions, or enrollment cycle from initial engagement through onboarding.
- Experience concurrently stewarding 20+ client, guest, or family connections at varying stages, supported by a structured tracking and prioritization approach.
- Capacity to supply specific examples of advisory decision-making, including instances where you counseled against your offering when alignment was absent.
- Professional-grade written correspondence experience with senior leadership, high-net-worth clients, or discerning audiences.
- Willingness to reside in or relocate within 60 days to one of these markets: Santa Barbara, CA; Santa Monica, CA; Orange County, CA; Roswell, GA; Chicago, IL; Charlotte, NC; Raleigh, NC; or Dallas-Fort Worth, TX.
- Authorized to work in the United States without visa sponsorship.
- Background in competitive private school admissions or selective program recruitment.
- Experience in luxury hospitality, VIP client services, or executive support capacities.
- Involvement in designing or optimizing enrollment workflows, standard operating procedures, or service protocols.
- Proficiency leveraging data and CRM analytics to enhance conversion quality, not merely velocity.
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-5531-US-Chicago-HeadofEnrollme
Head of Enrollment Operations, Alpha - $200,000/year USD
Crossover
linkedin
Chicago, IL
10-15 years $100.00/hr - $100.00/hr
Full time
13 April 2026
Top Skills:
AiBrand IdentityCrmForecastingHitHospitalityHubspotRecruitmentRelaySaleTarget Audience
96
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Job Description
Download Resume
Most enrollment positions prioritize throughput. This one is designed to uphold standards.
Alpha is developing one of the most forward-thinking school models globally. Our campuses integrate demanding academics, technology-enabled learning, and elevated expectations for both students and faculty. Students routinely exceed national learning benchmarks, supported by measurable evidence. Afternoon hours are dedicated to depth, autonomy, and practical competency development. The model delivers results—but only when paired with the right families.
This is your mandate.
You will control the entire enrollment experience for a campus, beginning with initial inquiry and concluding with onboarding. This is not a relay role. You determine how families perceive us, how thoroughly they grasp the model, and whether enrollment decisions reflect genuine alignment. You will evaluate compatibility, facilitate informed discussions, and advocate for rejection when circumstances warrant it. The objective is not enrollment maximization. The objective is fit.
We welcome candidates from elevated service sectors outside conventional education: independent schools, competitive programs, luxury hospitality, executive client services, premium membership platforms, or entrepreneurial leaders who have directly overseen high-value client relationships from start to finish. What counts is your capacity to orchestrate a sophisticated, multi-phase process with discernment, precision, and accountability.
If your professional background centers on delivering exceptional service where credibility, confidentiality, and experience integrity define brand identity, this role will resonate—simply applied to work that measurably transforms outcomes.
This is a full-time, salaried, on-site position. We are currently hiring across Santa Barbara, Santa Monica, Orange County, Roswell, Chicago, Charlotte, Raleigh, and Dallas-Fort Worth. Relocation assistance is provided.
What You Will Be Doing
Direct and deliver a high-trust, selective enrollment process that successfully onboards aligned families while safeguarding the integrity and academic performance of the Alpha model.
Basic Requirements
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-5531-US-Chicago-HeadofEnrollme
Alpha is developing one of the most forward-thinking school models globally. Our campuses integrate demanding academics, technology-enabled learning, and elevated expectations for both students and faculty. Students routinely exceed national learning benchmarks, supported by measurable evidence. Afternoon hours are dedicated to depth, autonomy, and practical competency development. The model delivers results—but only when paired with the right families.
This is your mandate.
You will control the entire enrollment experience for a campus, beginning with initial inquiry and concluding with onboarding. This is not a relay role. You determine how families perceive us, how thoroughly they grasp the model, and whether enrollment decisions reflect genuine alignment. You will evaluate compatibility, facilitate informed discussions, and advocate for rejection when circumstances warrant it. The objective is not enrollment maximization. The objective is fit.
We welcome candidates from elevated service sectors outside conventional education: independent schools, competitive programs, luxury hospitality, executive client services, premium membership platforms, or entrepreneurial leaders who have directly overseen high-value client relationships from start to finish. What counts is your capacity to orchestrate a sophisticated, multi-phase process with discernment, precision, and accountability.
If your professional background centers on delivering exceptional service where credibility, confidentiality, and experience integrity define brand identity, this role will resonate—simply applied to work that measurably transforms outcomes.
This is a full-time, salaried, on-site position. We are currently hiring across Santa Barbara, Santa Monica, Orange County, Roswell, Chicago, Charlotte, Raleigh, and Dallas-Fort Worth. Relocation assistance is provided.
What You Will Be Doing
- Controlling the complete enrollment pathway for prospective families, from initial outreach through final onboarding.
- Facilitating fit-assessment dialogues to establish compatibility before proposing solutions or advising subsequent actions.
- Overseeing 20+ concurrent family engagements across various enrollment phases, maintaining transparent status tracking and timely follow-up.
- Directing campus visits, shadow day experiences, and decision-stage discussions that transparently convey outcomes, expectations, and target audience.
- Sustaining precise CRM and enrollment documentation (HubSpot and SIS) to enable accurate forecasting, priority management, and service excellence.
- Deploying transactional or aggressive sales methods.
- Accepting families with poor alignment solely to achieve enrollment targets.
- Supervising large teams or navigating complex approval hierarchies.
- Distributing family experience ownership across multiple functions.
- Operating remotely. This position is intentionally campus-based.
Direct and deliver a high-trust, selective enrollment process that successfully onboards aligned families while safeguarding the integrity and academic performance of the Alpha model.
Basic Requirements
- 3+ years providing premium, individualized service in settings where service excellence directly influences brand standing (education, luxury hospitality, executive assistance, premium membership, or independently operated client services).
- Proven ownership of a complete client, admissions, or enrollment cycle from initial engagement through onboarding.
- Experience concurrently stewarding 20+ client, guest, or family connections at varying stages, supported by a structured tracking and prioritization approach.
- Capacity to supply specific examples of advisory decision-making, including instances where you counseled against your offering when alignment was absent.
- Professional-grade written correspondence experience with senior leadership, high-net-worth clients, or discerning audiences.
- Willingness to reside in or relocate within 60 days to one of these markets: Santa Barbara, CA; Santa Monica, CA; Orange County, CA; Roswell, GA; Chicago, IL; Charlotte, NC; Raleigh, NC; or Dallas-Fort Worth, TX.
- Authorized to work in the United States without visa sponsorship.
- Background in competitive private school admissions or selective program recruitment.
- Experience in luxury hospitality, VIP client services, or executive support capacities.
- Involvement in designing or optimizing enrollment workflows, standard operating procedures, or service protocols.
- Proficiency leveraging data and CRM analytics to enhance conversion quality, not merely velocity.
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-5531-US-Chicago-HeadofEnrollme