Director, Enterprise Strategy

Why you'll love working here:

• high-performance, people-focused culture

• our commitment that equity, diversity, and inclusion are fundamental to our work environment and business success, which helps employees feel valued and empowered to be their authentic selves

• learning and development initiatives, including workshops, Speaker Series events and access to LinkedIn Learning, that support employees' career growth

• membership in HOOPP's world class defined benefit pension plan, which can serve as an important part of your retirement security

• competitive, 100% company-paid extended health and dental benefits for permanent employees, including coverage supporting our team's diversity and mental health (e.g., gender affirmation, fertility and drug treatment, psychological support benefits of $2,500 per year, parental leave top-up, and a health spending account).

• optional post-retirement health and dental benefits subsidized at 50%

• yoga classes, meditation workshops, nutritional consultations, and wellness seminars

• the opportunity to make a difference and help take care of those who care for us, by providing a financially secure retirement for Ontario healthcare workers

Job Summary

The Director, Enterprise Strategy helps shape and drive HOOPP's enterprise strategy by turning complex problems into clear choices, actionable plans, and measurable outcomes. This role brings structure, insight, and analytical rigor to major strategic initiatives and ensures that HOOPP's long-term direction is informed by a strong understanding of uncertainty, resilience, and emerging risks.

Working closely with senior leaders across the organization, the Director leads core strategy processes, oversees enterprise-wide initiatives, and contributes to a total-enterprise view of resilience and performance. The role requires a strategist who is detail-oriented, intellectually curious, and able to operate independently while collaborating across investments, pensions, and enabling functions.

What You Will Do

Enterprise Strategy (Primary Focus – 70%)

• Lead the evolution and execution of HOOPP's enterprise strategy, including the annual strategy cycle, strategic planning materials, and Board updates.
• Run key enterprise initiatives, including the Strategic Initiative Groups (SIGs), ensuring issues are framed clearly, options are well-developed, and outcomes are measurable.
• Embed foresight and scenario thinking into strategy development to help HOOPP anticipate changes in markets, technology, policy, and member needs.
• Develop clear frameworks, decision tools, and "strategy on a page" materials to bring structure and alignment across the enterprise.
• Partner with the Office of the CEO and senior leaders to advance cross-enterprise strategic projects, operating model initiatives, and long-term organizational priorities.
• Prepare crisp, insightful materials for the Executive Team and Board that translate complexity into clear strategic choices.
• Proactively connect with leaders across the organization to gather insights, drive communication, and detect early strategic or risk signals that support better enterprise decision-making.

Enterprise Risk (Supporting Focus – 20%)

• Contribute to a modernized Annual Risk Report that highlights the strategic risks, opportunities, and resilience themes that matter most to HOOPP's long-term success.
• Help link strategy and risk by assessing how enterprise risks shape strategic choices and execution.
• Support the development of a Total Enterprise Approach, connecting financial, operational, human, and technological considerations into a unified resilience view.
• Work with senior leaders across Investments, Pensions, Finance, Technology, HR, and Legal to analyze cross-enterprise risks and improve decision-making.
• Apply a strategist's lens to emerging risks, translating uncertainty into insights that guide planning and resource allocation.

Leadership, Innovation, and Capability Building (10%)

• Support the VP in building a high-performing Strategy & Enterprise Risk team and ways of working.
• Mentor analysts and strategists, modelling structured problem-solving, high-quality analysis, and effective communication.
• Create tools, dashboards, and processes that make strategy and risk more data-driven, transparent, and actionable.
• Champion the use of technology, analytics, and AI to improve insight generation and streamline workflows across the team.

What You Bring

• 10+ years in strategy, management consulting, or enterprise planning; experience in investment or risk is an asset but not required.
• Graduate degree (MBA, MDes, or equivalent) in strategy, business, design, or innovation or related field. CFA or similar credentials considered an asset.
• Exceptional structured problem-solving, analytical capability, and attention to detail.
• Ability to lead complex initiatives independently, while influencing senior decision-makers with clear, compelling insights.
• Strong written and visual communication skills; able to create executive-ready presentations, memos, and decision materials.
• Comfort operating in ambiguity, framing unstructured problems, and driving clarity across functions.
• Experience supervising or mentoring junior team members.
• Curiosity, adaptability, and a commitment to high-quality, thoughtful work.

Core Competencies

• Strategic Thinking: Understands complex systems and can structure issues, choices, and trade-offs.
• Execution: Drives initiatives from framing to delivery, bringing order, discipline, and follow-through.
• Analytical Insight: Uses data, research, and synthesis to inform decisions and measure progress.
• Collaboration: Builds strong relationships and works effectively across divisions and domains.
• Leadership: Models high standards, supports others' growth, and brings clarity and steadiness to complex work.
• Communication: Produces compelling narratives for executives, Boards, and cross-functional teams.