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

Crossover; Worcester (MA); On-site; USD 180,000 - 220,000; Full time

Job summary

Alpha seeks a Director of Learning & Development to lead a campus cohort, coach Guides, and ensure three core outcomes: enthusiasm for learning, double-speed progress, and mastery of life skills. All work is in person and focuses on building a scalable, data-informed program across campuses.

You will oversee workshops, mentor Guides, analyze Coachbot data, and drive the coaching culture as Alpha expands its presence in the US.

Qualifications

• Bachelor's degree in Education, Psychology, Business, or related discipline; Master’s preferred.
• Minimum 5 years of professional experience in education, learning and development, coaching, or comparable field.
• Proven leadership experience managing teams of 5+ individuals.
• Experience creating and executing educational programs or training initiatives.
• Legal authorization to work in the United States.

Responsibilities

• Execute Alpha's 3 Promises across cohorts and Guides, ensuring genuine love for school and growth.
• Lead direct work with student cohorts and coach Guides with consistent expectations.
• Mentor and develop Guides using direct observation and feedback.
• Analyze Coachbot data to identify students needing additional support and provide it.
• Directly mentoring your assigned student cohort to model coaching and motivation.

Skills

Leadership

Coaching

Data-driven decision making

Education

Bachelor's degree in Education, Psychology, Business, or related discipline

Master's degree preferred

Job description

• In-person roles available in: Beverly Hills, CA; Piedmont, CA; Greenwich, CT; Boca Raton, FL; Miami, FL; Boston, MA; Raleigh, NC; New York City, NY; Seattle, WA (relocation assistance available)
• $200,000 annually, paid weekly | Health, dental, and vision coverage from day one

• In-person roles available in: Beverly Hills, CA; Piedmont, CA; Greenwich, CT; Boca Raton, FL; Miami, FL; Boston, MA; Raleigh, NC; New York City, NY; Seattle, WA (relocation assistance available)
• $200,000 annually, paid weekly | Health, dental, and vision coverage from day one

The greatest support you can offer a student who achieves 99% is to withhold the perfect score. Not out of apathy — but because you know they're capable of reaching 100%, and pretending otherwise is the true disservice. If this reasoning resonates, continue. If it feels severe, this position isn't a fit.

Students at Alpha don't passively absorb lectures. They advance through adaptive applications at double the speed of conventional classrooms while simultaneously developing practical life competencies. Your role is to ensure three core outcomes for every student in your cohort: genuine enthusiasm for learning, double-speed academic progress, and mastery of skills beyond traditional curricula. You will simultaneously develop the Guides who deliver these outcomes throughout your campus.

All choices are grounded in data, and all work is conducted in person. Your time divides between direct work with your student cohort and coaching the Guides under your leadership — with identical expectations for both: demonstrable growth, without compromise. When a Guide's session underperforms, you skip the paperwork; instead, you observe, discuss, and course-correct before the day ends.

You will witness reserved students present with confidence to adult audiences. You will see learners who once "despised school" request extended hours. And you will recognize that the high standard you maintained made these transformations possible, because upholding expectations is how you demonstrate belief in someone's potential.

You may be establishing a campus from the ground up, defining the foundational culture of the school. As the campus develops, your role evolves from operational founder to coaching executive, cultivating the team that extends Alpha's methodology throughout your territory.

What You Will Be Doing

• Facilitating one-hour interactive workshops on life skills and social-emotional learning (SEL) for K-8 students, covering areas such as public speaking and concentration, using Alpha's established framework
• Conducting daily motivational sessions designed to propel 100% of students toward weekly application milestones through age-appropriate mechanisms including school currency and competitive leaderboards
• Developing Guides via direct observation, specific feedback, and practical coaching to ensure they execute workshops with equivalent enthusiasm and accuracy
• Analyzing Coachbot data and individual student records to pinpoint students requiring additional support, then providing that support directly
• Directly mentoring your assigned student cohort, demonstrating the coaching and motivational techniques you expect every Guide to replicate

What You Won’t Be Doing

• Developing lesson plans or creating curriculum. Students engage with adaptive apps; your responsibility is elevating the people who guide them.
• Delivering traditional lectures to a seated class. You operate as 80% motivator, 20% content expert; if you prefer standing at a whiteboard, this role won't suit you.
• Compromising standards due to external pressure from parents or administrators. When a student reaches 99%, the response remains "not yet" — and you will be empowered to maintain that position.
• Spending your time in an office processing administrative documents. The majority of your day involves direct interaction with students and Guides.
• Waiting extended periods for performance assessment. Outcomes are visible in real time through Coachbot, and adjustments are made immediately.

Director Of Learning & Development Key Responsibilities

Execute Alpha's 3 Promises throughout your cohort and among the Guides under your supervision: every student develops genuine love for school, achieves learning at 2x traditional pace, and acquires authentic life skills.

Basic Requirements

• Currently residing in or prepared to relocate to Beverly Hills, CA; Piedmont, CA; Greenwich, CT; Boca Raton, FL; Miami, FL; Boston, MA; Raleigh, NC; New York City, NY; Seattle, WA (relocation assistance provided)
• Bachelor's degree in Education, Psychology, Business, or related discipline (Master's degree preferred; conventional teaching certifications not required)
• 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 leadership record managing teams of 5 or more individuals, including responsibility for hiring and performance-based termination decisions
• Background in coaching, mentoring, or delivering constructive feedback to enhance engagement and performance outcomes
• Direct experience working with children ages 5–14 in educational or developmental contexts
• Strong capability in leveraging data and 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
• Experience as an athletic coach, camp director, or youth program coordinator where you directly inspired children to achieve quantifiable goals
• History of coaching adults in positions where performance was actively measured and evaluated
• Natural ability to engage large groups of children. The caliber of presence that commands attention in a room full of 8-year-olds.

About Alpha

Join the team building school around student growth

Alpha reimagines the school day around faster learning, stronger mentorship, and more time for students to build real-world skills.

Roles with real student impact:

Alpha hires teachers (guides), operators, admissions experts, school & curriculum leaders, and remote team members.

Education work that pays like it matters:

Alpha offers six-figure roles for people ready to help build a radically better school experience.

A culture built for builders:

Alpha is fast-moving, ambitious, and student focused. It’s for people who want to improve the system, not maintain it.

Alpha is where you can do the most meaningful work of your career.

There is so much to cover for this exciting role, and space here is limited.

Working with us

This is a full-time, W2 employee position with immediate access to benefits (https://support.crossover.com/article/7581-w2-benefits-u-s-paychex-paid-only). All roles are year-long positions. The compensation level for this role is $200,000 USD/year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.