Youth Program Manager
$200,000 CAD Salaried employee 

Not accepting applications on crossover.com at this time.

Description

  • Toronto, Canada – on-site position
  • $200,000 CAD annually

The kindest thing you can do for a struggling eight-year-old is hold the line. If that notion unsettles you, this role is not for you. If it resonates, continue reading.

Alpha has dismantled conventional teaching. Students progress through academics via adaptive software at their own speed. No traditional lectures. No grade-level caps. What remains—and what matters above all—is what technology cannot provide: the character development, the drive, and the adult who maintains a standard each student didn't believe they could meet. That is your domain.

A typical morning might involve coaching a Guide using their Coachbot data, identifying precisely where a cohort is falling behind. By midday you're facilitating a live workshop with elementary and middle school students, executing a structured activity on public speaking or feedback delivery. Afternoons transition to motivation work: reviewing individual student progress data, activating Alpha's incentive architecture (campus currency, leaderboards), and re-engaging a reluctant seventh grader. Forty percent workshop facilitation, thirty percent motivation, thirty percent Guide coaching. You maintain your own student cohort throughout, ensuring your coaching remains rooted in direct practice.

You have likely been told you care too much about outcomes for the education field. Too metric-focused. Too willing to enforce a boundary that makes colleagues uneasy. Alpha was designed for precisely that individual. You demonstrate the model's effectiveness with your own students, elevate the Guides (Alpha's version of teachers) around you to that same benchmark, and as you produce results, your authority over campus program quality expands.

Uphold the standard. Transform the student. Apply today.

What you will be doing

  • Facilitating one-hour live workshops on character skills (public speaking, concentration, feedback exchange) for students in grades K-8, executing Alpha's structured playbook
  • Conducting motivation sessions leveraging Coachbot analytics and Alpha's incentive framework (campus currency, leaderboards) to achieve 100% student goal attainment
  • Coaching Guides on program adherence and standards maintenance, with each session yielding specific action steps for improvement
  • Managing your own student cohort to ensure your coaching remains anchored in real-time experience
  • Monitoring student satisfaction metrics, goal completion percentages, and Guide performance indicators weekly to identify underperformance promptly

What you will NOT be doing

  • Instructing mathematics, literacy, or any core academic content — adaptive software manages all academic instruction
  • Designing curriculum or creating workshop content from scratch (Alpha's playbook is your framework; the focus is execution excellence)
  • Coaching Guides on instructional methodology (Guides do not teach — you coach presence, motivation, and accountability)
  • Overseeing campus operations, financial planning, or administrative tasks
  • Lowering standards when a student is nearly there but hasn't arrived (the benchmark remains constant; your role is helping them reach it)

Key responsibilities

Fulfill Alpha's three commitments to every student: loving school, progressing at double the conventional rate, and developing real-world character skills.

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 experience in education, learning and development, coaching, or related area
  • Led a team of 5 or more individuals, including making hiring and termination decisions based on performance data
  • Hands-on experience working with youth ages 5-14 in an educational or developmental context
  • Built, launched, or substantially expanded a program, team, school, or initiative — not simply inherited or sustained an existing one
  • Comfortable operating in a school that deliberately rejects conventional pedagogy
  • Legal work authorization in Canada

Nice to have

  • Master's degree in Education, Psychology, Organizational Leadership, or related discipline
  • Coached sports, facilitated experiential programs, managed camps, or led youth initiatives at a scale requiring cohort management and outcome measurement
  • Transitioned from classroom teaching to program development or leadership in a different capacity (EdTech, tutoring enterprises, youth nonprofits, school intervention initiatives)
  • Experience applying learning analytics platforms to inform weekly coaching strategies
  • Conviction that the existing education system is fundamentally flawed and personal commitment to reimagining it

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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The Olympics of work

The Olympics of work

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