School Program Manager
$200,000 CAD Salaried employee 

Not accepting applications on crossover.com at this time.

Description

  • On-site position in Toronto, Canada
  • Annual salary: $200,000 CAD

The greatest support you can offer a struggling 8-year-old is maintaining high expectations. If this principle troubles you, this role is not a fit. If it resonates, continue reading.

Alpha has dismantled conventional instruction methods. Academic learning occurs through adaptive applications that allow students to progress at their individual pace. There are no lectures. No grade-level limitations. What remains—and what holds the greatest importance—is what technology cannot provide: life skills development, student motivation, and an adult who maintains standards students never imagined they could meet. This is your domain.

A typical morning may involve coaching a Guide using Coachbot analytics, identifying where a cohort needs support. By midday, you're facilitating a live workshop with K-8 students, executing a playbook activity focused on public speaking or feedback delivery. Afternoons transition to motivation work: reviewing individual student progress data, implementing Alpha's incentive framework (school currency, leaderboards), and re-engaging a reluctant 7th grader. The breakdown is forty percent workshops, thirty percent motivation, thirty percent coaching. Throughout this, you maintain your own student cohort, ensuring your coaching remains grounded in practice rather than theory.

You've likely heard you're overly results-oriented for education. Excessively data-focused. Too willing to maintain boundaries that make other adults uneasy. Alpha was designed for precisely this type of person. You demonstrate the model's effectiveness through your own students, elevate the Guides (Alpha's version of teachers) to the same standard, and as you produce results, your influence over campus-wide program quality expands.

Maintain the standard. Transform the student. Apply now.

What you will be doing

  • Facilitating one-hour live workshops on life skills (including public speaking, focus, and feedback practices) for K-8 students using Alpha's established playbook
  • Conducting motivation sessions that leverage Coachbot analytics and Alpha's incentive framework (school currency, leaderboards) to achieve 100% student goal completion
  • Providing coaching to Guides on program adherence and standards maintenance, with each session yielding specific improvement actions
  • Carrying your own student cohort to ensure your coaching remains rooted in direct, current experience
  • Monitoring student satisfaction scores, goal completion rates, and Guide performance data weekly to identify underperformance proactively

What you will NOT be doing

  • Delivering instruction in math, reading, or any academic content — adaptive applications manage all academic teaching
  • Developing curriculum or creating workshop activities from scratch (Alpha's playbook serves as your operating framework; excellence in execution is the standard)
  • Coaching Guides on pedagogical technique (Guides don't teach — your coaching focuses on energy, motivation, and accountability)
  • Overseeing campus operations, financial management, or administrative functions
  • Lowering standards when a student approaches but hasn't reached the goal (the standard remains constant; your role is helping them achieve it)

Key responsibilities

Fulfill Alpha's three commitments to every student: cultivating love of school, facilitating learning at twice the traditional pace, and developing real-world life skills.

Candidate requirements

  • On-site work in Toronto, Canada (remote or hybrid arrangements are not available)
  • Bachelor's degree in Education, Psychology, Business, or a related discipline
  • Minimum 5 years of experience in education, learning and development, coaching, or a related field
  • Experience leading a team of 5 or more people, including making hiring and termination decisions based on performance outcomes
  • Hands-on experience working with youth ages 5-14 in an educational or developmental context
  • Track record of building, launching, or substantially growing a program, team, school, or initiative — not merely sustaining an existing one
  • Willingness to work in a school that deliberately rejects traditional pedagogical approaches
  • Legal authorization to work in Canada

Nice to have

  • Master's degree in Education, Psychology, Organizational Leadership, or a related discipline
  • Experience coaching athletics, leading experiential programs, directing camps, or managing youth programs at a scale requiring cohort management and outcome measurement
  • Transition from classroom teaching to building or operating programs in a different capacity (EdTech, tutoring businesses, youth nonprofits, school intervention teams)
  • Familiarity with learning analytics platforms for weekly coaching decision-making
  • Conviction that the current education system is fundamentally flawed and personal commitment to its 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

Applying for a role? Here’s what to expect.

Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.

Chat-style
screening interview.
STEP 1

Chat-style
screening interview.

Cognitive 
aptitude test.
STEP 2

Cognitive 
aptitude test.

Prove real-world 
job skills.
STEP 3

Prove real-world 
job skills.

Interview with the hiring manager.
STEP 4

Interview with the hiring manager.

Pass
proctored test.
STEP 5

Pass
proctored test.

Accept job offer.
STEP 6

Accept job offer.

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