Crossover
Director of Learning & Development, Alpha - $200,000/year USD
Crossover, Chicago, Illinois, United States, 60290
Director of Learning & Development, Alpha - $200,000/year USD
Join to apply for the
Director of Learning & Development, Alpha - $200,000/year USD
role at
Crossover
1 day ago Be among the first 25 applicants
Join to apply for the
Director of Learning & Development, Alpha - $200,000/year USD
role at
Crossover
This range is provided by Crossover. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.
Base pay range $100.00/hr - $100.00/hr
On-site position in Bethesda, MD; Boston, MA; Chicago, IL; Fort Lauderdale, FL; Seattle, WA; or CA: East Bay (San Francisco), Palo Alto, Santa Monica, or Los Angeles
$200,000 annual salary, paid weekly. Health benefits from day one, HSA/FSA options, 401(k) Roth
Relocation assistance provided
Alpha is transforming the school experience. Our students engage with adaptive applications rather than traditional lectures, progressing through material at twice the standard pace while developing practical life competencies. Your role centers on ensuring our "3 Promises" reach every learner in your cohort and equipping our Guides with the tools to replicate that success.
You will combine exceptional coaching expertise with dynamic presentation skills, transforming workshops, data-informed team sessions, and precise feedback into powerful development experiences. If you have exceeded benchmarks, converted struggling performers into high achievers, or consistently reject mediocrity, we invite you to help us build excellence.
What makes Alpha different?
Competitive compensation for high-cost markets – elevated pay structure reflecting the cost of living in these metropolitan regions
Comprehensive benefits package – full health coverage and substantial paid time off
Relocation support – offered to exceptional candidates
Development-focused environment – access to coaching, professional training, and defined advancement opportunities
What You Will Be Doing
Developing and coaching Guides to deliver Alpha's workshops at a world-class standard
Building Guide Playbooks that document facilitation best practices, design engaging learning experiences, and address common obstacles
Delivering consistent, targeted feedback to Guides that drives higher student engagement and outcomes
Personally coaching a small student cohort to demonstrate advanced motivational and mentoring techniques
What You Won’t Be Doing
Developing lesson plans – Guides support students working through adaptive apps; you focus on training them to become outstanding motivators
Compromising on standards – when the passing grade is 100%, you will uphold that expectation
Running dull training sessions – you will coach Guides through dynamic, interactive, high-impact professional development
Director Of Learning & Development Key Responsibilities Train Guides and mentor students to ensure every learner in your cohort enjoys school, progresses at 2× speed, and develops essential life skills. No exceptions.
Basic Requirements
Currently located in or prepared to relocate for on-site work at one of the Alpha Campuses (Bethesda, MD; Boston, MA; Chicago, IL; Fort Lauderdale, FL; Seattle, WA; or CA: East Bay (San Francisco), Palo Alto, Santa Monica, or Los Angeles)
Hold a Bachelor's degree in any discipline.
Minimum 5 years of professional experience in education, learning and development, coaching, or a closely related area.
Proven track record of creating and executing innovative educational programs, curricula, or training solutions.
Demonstrated leadership and mentorship capabilities with experience building, managing, and inspiring high-performing teams.
Background working with young people (ages 5-18) in educational or developmental settings.
Strong analytical skills and ability to leverage data and metrics for decision-making and ongoing improvement.
Legal authorization to work in the United States
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 www.crossover.com/help-and-faqs for more details on this topic.
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Director of Learning & Development, Alpha - $200,000/year USD
role at
Crossover
1 day ago Be among the first 25 applicants
Join to apply for the
Director of Learning & Development, Alpha - $200,000/year USD
role at
Crossover
This range is provided by Crossover. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.
Base pay range $100.00/hr - $100.00/hr
On-site position in Bethesda, MD; Boston, MA; Chicago, IL; Fort Lauderdale, FL; Seattle, WA; or CA: East Bay (San Francisco), Palo Alto, Santa Monica, or Los Angeles
$200,000 annual salary, paid weekly. Health benefits from day one, HSA/FSA options, 401(k) Roth
Relocation assistance provided
Alpha is transforming the school experience. Our students engage with adaptive applications rather than traditional lectures, progressing through material at twice the standard pace while developing practical life competencies. Your role centers on ensuring our "3 Promises" reach every learner in your cohort and equipping our Guides with the tools to replicate that success.
You will combine exceptional coaching expertise with dynamic presentation skills, transforming workshops, data-informed team sessions, and precise feedback into powerful development experiences. If you have exceeded benchmarks, converted struggling performers into high achievers, or consistently reject mediocrity, we invite you to help us build excellence.
What makes Alpha different?
Competitive compensation for high-cost markets – elevated pay structure reflecting the cost of living in these metropolitan regions
Comprehensive benefits package – full health coverage and substantial paid time off
Relocation support – offered to exceptional candidates
Development-focused environment – access to coaching, professional training, and defined advancement opportunities
What You Will Be Doing
Developing and coaching Guides to deliver Alpha's workshops at a world-class standard
Building Guide Playbooks that document facilitation best practices, design engaging learning experiences, and address common obstacles
Delivering consistent, targeted feedback to Guides that drives higher student engagement and outcomes
Personally coaching a small student cohort to demonstrate advanced motivational and mentoring techniques
What You Won’t Be Doing
Developing lesson plans – Guides support students working through adaptive apps; you focus on training them to become outstanding motivators
Compromising on standards – when the passing grade is 100%, you will uphold that expectation
Running dull training sessions – you will coach Guides through dynamic, interactive, high-impact professional development
Director Of Learning & Development Key Responsibilities Train Guides and mentor students to ensure every learner in your cohort enjoys school, progresses at 2× speed, and develops essential life skills. No exceptions.
Basic Requirements
Currently located in or prepared to relocate for on-site work at one of the Alpha Campuses (Bethesda, MD; Boston, MA; Chicago, IL; Fort Lauderdale, FL; Seattle, WA; or CA: East Bay (San Francisco), Palo Alto, Santa Monica, or Los Angeles)
Hold a Bachelor's degree in any discipline.
Minimum 5 years of professional experience in education, learning and development, coaching, or a closely related area.
Proven track record of creating and executing innovative educational programs, curricula, or training solutions.
Demonstrated leadership and mentorship capabilities with experience building, managing, and inspiring high-performing teams.
Background working with young people (ages 5-18) in educational or developmental settings.
Strong analytical skills and ability to leverage data and metrics for decision-making and ongoing improvement.
Legal authorization to work in the United States
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 www.crossover.com/help-and-faqs for more details on this topic.
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