Youth Development Manager
$200,000 CAD Salaried employee 

Not accepting applications on crossover.com at this time.

Description

  • Toronto, Canada – on-site position
  • Annual compensation: $200,000 CAD

The most effective support for an 8-year-old who's struggling is maintaining high expectations. If that statement creates discomfort, this role isn't the right fit. If it resonates, continue reading.

Alpha has reimagined conventional education. Academic learning happens through adaptive applications at each student's individual pace. No traditional lectures. No grade-based limitations. What remains—and what matters above all—is what technology cannot provide: essential life skills, sustained motivation, and an adult who maintains standards students didn't believe they could meet. That responsibility is yours.

A typical morning could involve coaching a Guide using Coachbot analytics to identify exactly where a cohort is falling behind. By midday you're facilitating live workshops with elementary and middle school students, implementing playbook activities focused on public speaking or constructive feedback. Afternoons transition to motivation work: reviewing individual student progress data, applying Alpha's incentive framework (campus currency, performance leaderboards), and re-engaging a reluctant 7th grader. The split is forty percent workshops, thirty percent motivation work, thirty percent coaching. Throughout, you maintain your own student cohort, ensuring your coaching remains rooted in direct practice rather than theory.

You've likely heard you're overly results-oriented for the education sector. Too reliant on data. Too insistent on boundaries that make other educators uneasy. Alpha was designed for precisely that profile. You demonstrate the model's effectiveness through your own student outcomes, elevate the Guides (Alpha's teacher equivalent) to match that standard, and as you produce results, your influence on school-wide program quality expands.

Maintain the standard. Transform the student. Submit your application.

What you will be doing

  • Facilitating hour-long live workshops on essential life skills (public speaking, concentration, feedback exchange) for students in grades K-8, using Alpha's structured playbook
  • Conducting motivation sessions that leverage Coachbot analytics and Alpha's incentive architecture (campus currency, leaderboards) to achieve 100% student goal attainment
  • Coaching Guides on maintaining program fidelity and upholding standards, with each session yielding specific improvement actions
  • Managing your own student cohort to keep your coaching anchored in direct, ongoing experience
  • Monitoring student satisfaction metrics, goal completion percentages, and Guide performance indicators weekly to identify underperformance promptly

What you will NOT be doing

  • Delivering instruction in mathematics, literacy, or other academic content — adaptive applications manage all academic teaching
  • Developing curriculum or designing workshop content from scratch (Alpha's playbook serves as your operational framework; success is measured by execution excellence)
  • Training Guides on instructional methods (Guides don't lecture — your focus is coaching energy, motivation, and accountability systems)
  • Overseeing campus operations, financial planning, or administrative functions
  • Lowering standards when a student approaches but hasn't met the benchmark (expectations remain constant; your role is helping them achieve it)

Key responsibilities

Fulfill Alpha's three core commitments to every student: fostering genuine enthusiasm for school, enabling learning at twice the conventional rate, and developing practical life skills for the real world.

Candidate requirements

  • On-site presence in Toronto, Canada (remote or hybrid arrangements not 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 fields
  • Leadership experience managing a team of 5 or more, including responsibility for hiring and performance-based terminations
  • Hands-on experience working with children ages 5-14 in educational or developmental contexts
  • Track record of building, launching, or substantially scaling a program, team, school, or initiative — not merely sustaining existing operations
  • Alignment with a school model that intentionally moves away from traditional educational approaches
  • Legal work authorization for Canada

Nice to have

  • Master's degree in Education, Psychology, Organizational Leadership, or related discipline
  • Background coaching sports, leading experiential education programs, directing camps, or managing youth programs at a scale requiring cohort management and outcome measurement
  • Transitioned from classroom teaching to program development or operations roles in different capacities (EdTech companies, tutoring enterprises, youth-focused nonprofits, school intervention programs)
  • Proficiency using learning analytics platforms to inform weekly coaching strategies
  • Conviction that the existing education system requires fundamental redesign and personal commitment to that transformation

Meet a successful candidate

Watch Interview
Braden Pomerantz
Braden  |  Head Guide
United States

Braden knew he wanted to work with students. He just didn’t want the old version of the job. After years of coaching, debate, and searching ...

Meet Braden

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Cognitive 
aptitude test.

Prove real-world 
job skills.
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job skills.

Interview with the hiring manager.
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Pass
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Accept job offer.
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Accept job offer.

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