Demo

Director of Learning & Development, Alpha - $200,000/year USD

Crossover
Greenwich, CT Full Time
POSTED ON 4/14/2026
AVAILABLE BEFORE 7/6/2026
  • On-site role in Greenwich, CT | Bethesda, MD | Chicago, IL | Piedmont, CA
  • $200,000 annual salary, paid weekly. Full health, dental, and vision benefits from day one
  • Relocation assistance provided

The kindest thing you can do for a student who achieved 99% is to never round it up to 100%. If that statement troubles you, this role is not a fit. If it resonates, continue reading.

Alpha students do not passively listen to lectures. They advance rapidly through adaptive technology, absorb material at double the speed of conventional classrooms, and develop practical life competencies simultaneously. Your responsibility is to ensure three commitments are met for every child in your group: they enjoy learning, they progress at 2x speed, and they acquire capabilities beyond what traditional curricula provide. You will also develop the Guides who execute these same commitments throughout your campus.

Your day begins with data review. Analytics reveal which students are progressing and which require intervention. By mid-morning, you are facilitating a live session, guiding K-8 learners through exercises in public speaking or concentration using Alpha's established framework. Post-lunch, you observe a Guide's delivery, then provide them with three concrete steps to refine their execution. On certain days, you serve as the motivational catalyst during a group session, transforming leaderboard rankings into momentum. You remain directly engaged with your own student group while simultaneously building Guides capable of meeting your benchmark, and as they rise, your influence scales from one group to an entire site.

You will witness reserved children present with confidence to adults. You will see a student who once "despised school" request to remain after hours. And you will recognize that the standard you maintained is precisely what enabled their growth, because upholding expectations is how you demonstrate belief in someone's potential.

If you have exceeded targets, transformed low performers into high achievers, and you are prepared to do the same for children: submit your application now.

What You Will Be Doing

  • Facilitating one-hour live sessions with K-8 students covering life competencies such as public speaking, concentration, and feedback exchange, using Alpha's structured framework
  • Developing Guides through direct observation, specific feedback, and practical coaching to ensure they execute sessions with equivalent energy and accuracy
  • Conducting daily motivational sessions designed to drive 100% of students toward weekly learning targets using developmentally appropriate tools like campus currency and competitive leaderboards
  • Analyzing Coachbot data and student records to pinpoint learners requiring support, then delivering personal intervention
  • Directly mentoring your own small student group, demonstrating the coaching and motivational techniques you expect from all Guides

What You Won’t Be Doing

  • Creating lesson plans or developing curriculum. Students advance through adaptive platforms; your focus is on making the people supporting them exceptional.
  • Delivering traditional lectures. Your role is 80% performance, 20% content expertise; if you prefer standing at a whiteboard, this is not the position.
  • Accepting "almost there" as sufficient. Complete mastery is the standard, and lowering it does not serve students.
  • Spending your time in an office handling administrative tasks. The majority of your day is spent directly engaging with students and Guides.

Director Of Learning & Development Key Responsibilities

Execute Alpha's 3 Promises: every child enjoys school, learns at 2x speed, and develops life skills, throughout your group and the groups led by your Guides.

Basic Requirements

  • Currently located in or willing to relocate to Greenwich, CT; Bethesda, MD; Chicago, IL; or Piedmont, CA (relocation assistance available)
  • Bachelor's degree in Education, Psychology, Business, or related discipline
  • Minimum 5 years of professional experience in education, learning and development, coaching, or related area
  • Demonstrated experience designing and executing educational programs, curricula, or training systems
  • Proven history of managing a team of 5 or more individuals, including recruitment and performance-driven termination decisions
  • Experience providing coaching, mentorship, or actionable feedback to enhance engagement and performance outcomes
  • Experience working directly with youth aged 5-14 in educational or developmental contexts
  • Skilled in leveraging data and performance metrics to inform decisions and drive continuous improvement
  • Legal authorization to work in the United States

Nice-to-have Requirements

  • Master's degree in Education, Psychology, or Business
  • Prior experience as an athletic coach, camp director, or youth program leader where you directly motivated children to achieve quantifiable goals
  • Experience coaching adults in environments where performance was measured and evaluated
  • Ability to engage large groups of children with presence. The type of energy that commands attention from a room full of 8-year-olds.

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.

Crossover Job Code: LJ-5628-US-Greenwic-DirectorofLear

Salary : $200,000

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