Demo

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

Crossover
Elgin, IL Full Time
POSTED ON 5/5/2026
AVAILABLE BEFORE 7/27/2026
  • In-person locations: Beverly Hills, CA; La Jolla (San Diego), CA; Piedmont, CA; South Bay (LA), CA; Greenwich, CT; Boca Raton, FL; Miami Beach, FL; Chicago, IL; Boston, MA; Bethesda, MD; Raleigh, NC; New York City, NY (relocation assistance available)
  • $200,000 annual salary, paid weekly | Health, dental, and vision benefits begin day one

The greatest support you can offer a student achieving 99% is refusing to label it 100%. This isn't indifference—it reflects your conviction that they can reach the full mark, and that lowering expectations constitutes the true disservice. If this reasoning resonates, continue reading. If it strikes you as severe, you will find this position challenging.

Students at Alpha do not attend traditional lectures. They advance through adaptive applications at double the speed of conventional classrooms while simultaneously developing practical life competencies. Your role ensures three commitments are fulfilled for every student in your cohort: genuine enthusiasm for school, accelerated learning at 2x pace, and acquisition of skills absent from standard curricula. You will also develop the Guides who uphold these same commitments across your campus.

Data informs every choice, and daily operations are conducted in person. Your time divides between your personal student cohort and the Guides under your leadership—with identical expectations for both: quantifiable advancement, without compromise. When a Guide's session underperforms, you do not file documentation; you observe, analyze, and address the issue that same afternoon.

You will observe reserved children presenting with assurance to adults. You will witness students who previously "despised school" requesting extended hours. And you will recognize that the standard you maintained made this possible, because upholding expectations demonstrates your belief in their capacity to exceed them.

You may initiate an entirely new campus from the ground up, establishing the foundational culture for the institution. As the campus develops, your emphasis transitions from operational startup mode to coaching leadership, cultivating the team that extends Alpha's methodology throughout your region.

If this appeals to you, submit your application now.

What You Will Be Doing

  • Facilitating one-hour live workshops in life skills and social-emotional learning (SEL) for K-8 students, covering areas such as public speaking and concentration, using Alpha's established playbook
  • Conducting daily motivation sessions designed to propel 100% of students toward their weekly application goals through age-appropriate incentive structures including school currency and leaderboards
  • Developing Guides via observation, precise feedback, and direct coaching so they execute workshops with equivalent energy and accuracy
  • Analyzing Coachbot analytics and student data to pinpoint students requiring intervention, then providing that intervention yourself
  • Directly mentoring your assigned student cohort, demonstrating the coaching and motivational techniques you expect every Guide to employ

What You Won’t Be Doing

  • Creating lesson plans or developing curriculum. Students engage with adaptive applications; your responsibility is elevating the people who support them.
  • Delivering traditional classroom lectures. Your role is 80% performance, 20% content expertise; if you prefer standing at a whiteboard, this position is not suitable.
  • Compromising standards due to pressure from parents or administration. When a student achieves 99%, the response is "not yet"—and you will have institutional support to maintain that boundary.
  • Spending time in an office processing administrative documents. The majority of your day involves direct interaction with students and Guides.
  • Awaiting delayed performance reviews. Data is available in real time through Coachbot, and adjustments occur immediately.

Director Of Learning & Development Key Responsibilities

Ensure Alpha's 3 Promises are realized across your cohort and among the Guides you lead: every student develops a genuine love for school, learns at 2x traditional pace, and acquires authentic life skills.

Basic Requirements

  • Currently located in or prepared to relocate to Beverly Hills, CA; La Jolla (San Diego), CA; Piedmont, CA; South Bay (LA), CA; Greenwich, CT; Boca Raton, FL; Miami Beach, FL; Chicago, IL; Boston, MA; Bethesda, MD; Raleigh, NC; New York City, NY (relocation assistance available)
  • Bachelor's degree in Education, Psychology, Business, or related discipline (Master's degree preferred; conventional teaching certifications are not sought)
  • Minimum 5 years of professional experience in education, learning and development, coaching, or comparable field
  • Demonstrated experience creating and executing educational programs, curricula, or training initiatives
  • Proven history of managing a team of 5 or more individuals, including responsibility for hiring and performance-related termination decisions
  • Experience providing coaching, mentorship, or constructive feedback to enhance engagement and performance outcomes
  • Prior work with youth ages 5–14 in educational or developmental contexts
  • Demonstrated ability to leverage data and metrics for decision-making and continuous improvement
  • Legal authorization to work in the United States

Nice-to-have Requirements

  • Master's degree in Education, Psychology, or Business
  • Experience as an athletic coach, camp director, or youth program leader where you directly motivated children to achieve quantifiable goals
  • Background coaching adults in positions where performance was measured and evaluated
  • Ability to engage large groups of children with confidence. The type of presence that commands attention in a room 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-Elgin-DirectorofLear.014

Salary : $200,000

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