Director of Program & Coaching Strategy

Team: Project Management

Location: Canada

Commitment: Full-time

Workplace Type: remote

Accountabilities:

The Director of Program & Coaching Strategy will oversee the development, execution, and continuous improvement of coaching and learning programs. This role requires a balance of strategic vision, operational excellence, and strong stakeholder management. Key responsibilities include:

• Building and scaling a comprehensive executive coaching system, including coach sourcing, evaluation, onboarding, and quality management processes.
• Designing repeatable frameworks and playbooks to ensure consistent, high-quality coaching experiences.
• Developing coach-member matching strategies and scalable delivery models, including group coaching initiatives.
• Creating systems to measure coaching effectiveness, member satisfaction, retention, and overall program impact.
• Managing monthly leadership masterclasses, including speaker coordination, content alignment, event execution, and post-event engagement.
• Building and maintaining a resource library and structured leadership event calendar aligned with member development goals.
• Implementing progress tracking systems, dashboards, milestone frameworks, and accountability processes.
• Partnering with leadership and operations teams to align programs with growth, retention, referral, and revenue objectives.
• Identifying opportunities for automation, strategic partnerships, program improvements, and scalable delivery solutions.
• Owning key performance indicators related to member experience, retention, lifetime value, and referral growth.
• Recruiting, training, and supporting coaches and subject matter experts to strengthen the program ecosystem.

Requirements:

The ideal candidate is a strategic and hands-on program leader with experience building learning, coaching, or community-driven initiatives. You should be comfortable operating in an entrepreneurial environment where ownership, adaptability, and execution are highly valued. Required qualifications include:

• 4+ years of experience building or scaling coaching, learning, education, or member-focused programs.
• Experience designing coaching networks, learning programs, leadership initiatives, or operational frameworks.
• Strong understanding of adult learning principles, accountability systems, and coach enablement strategies.
• Ability to translate ideas into scalable systems, processes, and operational workflows.
• Strong strategic thinking combined with the ability to execute independently.
• Experience working in fast-paced, founder-led, or startup environments where priorities can evolve quickly.
• Excellent communication, relationship-building, and stakeholder management skills.
• Strong analytical mindset with the ability to track performance metrics and improve outcomes.
• Ability to balance empathy and member-focused thinking with operational discipline.
• Passion for professional development, leadership growth, and creating meaningful impact.

Benefits:

• Fully remote position with Canada-based candidates preferred.
• Revenue share compensation model with significant upside tied to program growth and retention.
• Opportunity to earn at a founder-equivalent level while benefiting from an established business foundation.
• High level of autonomy and ownership in shaping a growing leadership development ecosystem.
• Direct collaboration with executive leadership and cross-functional teams.
• Opportunity to build scalable systems and programs that impact hundreds of technology professionals.
• Work with a diverse group of coaches, speakers, operations specialists, and community leaders.
• Career growth opportunity within a rapidly expanding organization.