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Director of Learning & Development, Alpha

Job in Boston, Suffolk County, Massachusetts, 02298, USA
Listing for: Crossover
Full Time position
Listed on 2026-03-10
Job specializations:
  • Education / Teaching
    Education Administration, Training Consultant
Salary/Wage Range or Industry Benchmark: 200000 USD Yearly USD 200000.00 YEAR
Job Description & How to Apply Below
Position: Director of Learning & Development, Alpha - $200,000/year USD

Locations & Compensation

  • On-site in Bethesda, MD;
    Chicago, IL;
    Palo Alto, CA;
    Piedmont, CA
  • Annual salary of $200,000 paid weekly. Comprehensive health, dental, and vision coverage from day one.
  • Relocation assistance provided

Alpha is transforming the experience of education. Students here don't passively absorb lectures—they race through adaptive learning platforms, achieve mastery at double the conventional pace, and acquire practical life competencies in parallel. Your role centers on ensuring our "3 Promises" become reality for each student in your cohort, while equipping our Guides with the skills to deliver the same outcomes.

You will fuse exceptional coaching expertise with dynamic facilitation presence, converting workshops, metrics-driven team rallies, and precise developmental feedback into powerful learning experiences. If you have exceeded benchmarks, transformed struggling performers into top achievers, or consistently reject mediocrity, we invite you to help us cultivate excellence.

Why Alpha?
  • Competitive metropolitan compensation – elevated salary structure reflecting the living costs in these urban markets, above our baseline Guide positions
  • Strong benefits and leave policies – full health benefits and substantial paid time off
  • Support for relocation – offered to exceptional candidates
  • Development-oriented environment – access to coaching, professional training, and defined advancement opportunities
What You Will Be Doing
  • Developing and coaching Guides to facilitate Alpha workshops at world‑class standards
  • Building Guide Playbooks that document facilitation best practices, design of engaging learning experiences, and solutions to common obstacles
  • Delivering consistent, practical feedback to Guides aimed at increasing student engagement and learning outcomes
  • Personally coaching a limited cohort of students, demonstrating advanced motivational and instructional techniques
What You Won’t Be Doing
  • Authoring curriculum content – Guides support student learning through adaptive software; you concentrate on training them to excel as motivators
  • Compromising expectations – when our mastery standard is 100%, your responsibility is to uphold that threshold
  • Running dull professional development – you will lead Guides through dynamic, experiential, high‑impact training sessions
Director Of Learning & Development

Key Responsibilities

Develop Guides and students to guarantee that every learner in your cohort loves attending school, achieves learning at 2× the standard rate, and gains essential life competencies. Zero exceptions.

Basic Requirements
  • Currently residing in or prepared to relocate for on‑site work at one of Alpha's campuses (Bethesda, MD; Chicago, IL; Palo Alto, CA; Piedmont, CA)
  • Hold a Bachelor's degree in any discipline.
  • Minimum of 5 years of professional experience in education, learning and development, coaching, or a closely related discipline.
  • Proven track record developing and executing innovative educational programs, curricula, or training solutions.
  • Robust leadership and mentoring capabilities with a history of building, managing, and inspiring high‑performing teams.
  • Background working with young people (ages 5-18) in an educational or developmental setting.
  • Competence in data analysis and leveraging metrics to inform decisions and drive continuous improvement.
  • Legal authorization to work in the United States
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 role 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.

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