Associate Director, Coaching & Leadership Development

OMERS•Toronto, ON

2d•CA$122,000 - CA$188,000•Remote

About The Position

The Associate Director, Coaching & Leadership Development will establish and lead an internal coaching practice that supports senior leaders and teams across the organization, as well as leading the design and delivery of enterprise leadership development and high potential programs. This role is responsible for designing a scalable, high‑quality coaching culture strengthening leadership capability and performance. The role blends enterprise program design, coaching and facilitation, partnering closely with senior leaders, HRBPs, and the Talent Management team to embed coaching as a leadership capability and development tool. This role may also have people leadership accountabilities.

Requirements

7-10 years of progressive experience in leadership development, executive coaching, or organizational development roles.
Demonstrated experience coaching senior and executive leaders in complex, matrixed organizations.
Proven ability to design and scale leadership or coaching programs at an enterprise level.
Strong facilitation skills with the ability to engage senior audiences.
Formal coaching training and certification (e.g., ICF or equivalent)
University degree in Human Resources, Business, or related discipline

Responsibilities

Establish and Lead an Internal Coaching Culture: Design and implement an internal coaching framework aligned to the organization’s leadership strategy and values. Define coaching standards, governance, ethics, and quality controls to ensure consistency and credibility. Determine where internal coaching is most effective versus external coaching, and manage a high quality, aligned roster of external coaches. Build tools, resources, and processes to scale coaching across leadership and deeper in the organization over time.
Senior Leader Coaching: Provide 1:1 and small‑group coaching to senior leaders: supporting transitions, performance, leadership impact, and enterprise mindset. Lead a community of practice to ensure the ongoing development and alignment to standards of an internal roster of trained coaches. Coach leaders on complex topics including influence, decision‑making, ambiguity, resilience, leading through change, etc. Serve as a trusted thought partner to senior leaders, balancing challenge and support. Educate leaders on the value of coaching and help normalize coaching as a strategic leadership tool.
Needs Assessment and Strategy: Leading the strategy, design and delivery of innovative leadership and team development programs, including flagship, transitional, and targeted leadership development initiatives and other offerings to drive professional growth and accountability aligned with our enterprise Leadership Capabilities framework and business needs. Developing learning paths that employ blended delivery methods and best-in-class methodologies to deliver a sustained learning experience that achieves long-term outcomes. Consulting with business leaders and HR Business Partners to understand their needs and aligning leadership and team development solutions to meet them. Building strong relationships with business leaders to identify appropriate opportunities for sponsorship, championship, engagement and alignment. Maintaining up to date understanding of global best practices and market benchmarks through white papers, thought partnerships and other channels.
Design and Development: Working with various business and HR stakeholders to design and develop blended learning experiences and materials aligned with adult learning principles and innovative, best-in-class learning standards. Leading the sourcing, evaluation, contracting and relationship management with external vendors, reviewing vendor material on a continual basis while having an ever-constant eye to market trends and innovation. Developing detailed plans for design and deployment of programs, including budgets, communication plans, and delivery planning. Overseeing a roster of internal and external facilitators to deliver initiatives, and facilitating initiatives as required including in-person, virtual, and hybrid formats.
Strategy, Measurement & Continuous Improvement: Define success measures and outcomes for coaching and leadership development initiatives (e.g., leader impact, engagement, retention, readiness). Use qualitative and quantitative insights to refine the coaching practice and ensure it delivers business and people outcomes. Stay current on external best practices in coaching and leadership development.