Director of Program & Coaching Strategy

📋 Description Lead development, execution, and continuous improvement of coaching and learning programs. Build and scale executive coaching systems: sourcing, onboarding, evaluation, quality management. Design repeatable frameworks and playbooks for consistent coaching experiences. Develop coach-member matching strategies and scalable delivery models, including group coaching. Create systems to measure coaching effectiveness, member satisfaction, retention, and impact. Oversee monthly leadership masterclasses, speaker coordination, and post-event engagement. 🎯 Requirements 4+ years building or scaling coaching, learning, or member-focused programs. Experience designing coaching networks, learning programs, leadership initiatives, or operational Strong understanding of adult learning principles, accountability systems, and coach enablement. Ability to translate ideas into scalable systems, processes, and workflows. Strategic thinking with the ability to execute independently. Experience in fast-paced, founder-led, or startup environments with evolving priorities. 🎁 Benefits Fully remote position with Canada-based candidates preferred. Revenue share with upside tied to program growth and retention. Opportunity to earn at founder-equivalent level within an established business. Autonomy to shape a growing leadership development ecosystem. Direct collaboration with executive leadership and cross-functional teams. Opportunity to build scalable systems impacting hundreds of technology professionals.