Director of Program & Coaching Strategy in Canada Creek, Nova Scotia at Jobgether

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Director of Program & Coaching Strategy based in Canada.

This role offers the opportunity to lead and scale a high-impact coaching and leadership development ecosystem designed for ambitious technology professionals.
The Director of Program & Coaching Strategy will own the systems, processes, and experiences that drive member transformation, engagement, and long-term success.
You will combine strategic thinking with operational execution to build scalable coaching programs, learning experiences, and community initiatives.
Working closely with executive leadership and cross-functional teams, you will shape programs that help professionals advance into senior leadership positions.
This position is ideal for an entrepreneurial operator who thrives in fast-moving environments and enjoys building structured solutions from the ground up.
You will have the autonomy to design innovative approaches, optimize delivery models, and directly influence growth, retention, and customer outcomes.

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.

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.

• 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.