Associate 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 Associate Director, Enterprise Strategy helps shape and advance HOOPP’s enterprise strategy. The role turns complex issues into clear choices, practical plans, and measurable results.

This position supports the full enterprise strategy cycle and leads structured innovation efforts, including the development and testing of new business models, offerings, and capabilities. The Associate Director integrates strategic risk, AI strategy, and emerging trends into planning and decision-making.

Working closely with senior leaders and teams across the organization, this role brings together strategy, innovation, and risk to support sound decision-making and long-term resilience. The role requires clear thinking, strong communication skills, and the ability to guide work from idea through launch.

What you will do:

• Support the annual enterprise strategy process, including priority setting, planning, and progress reporting.

• Turn complex business issues into clear options and recommendations.

• Prepare clear and well-structured presentations and written materials for senior leaders and the Board.

• Provide regular updates on strategy progress and key initiatives.

• Build strong working relationships across teams and with external partners.

• Lead structured innovation efforts from idea generation through testing and launch planning.

• Identify opportunities for new business models, services, partnerships, and enterprise capabilities.

• Help shape and advance HOOPP’s AI strategy, including identifying high-value use cases and governance considerations.

• Develop business cases, operating plans, and clear success measures for new initiatives.

• Facilitate workshops and working sessions to generate ideas and align stakeholders.

• Support tracking and oversight of the innovation pipeline.

• Monitor external trends in markets, technology, policy, and member needs, and assess their impact on HOOPP.

• Integrate strategic risk and uncertainty into planning and decision-making.

• Ensure new initiatives align with HOOPP’s risk appetite and long-term resilience goals.

• Translate risk insights into practical actions and recommendations.

• Facilitate cross-functional discussions to support clear and timely decisions.

• Encourage the thoughtful use of data, analytics, and AI tools to improve insight and efficiency.

• Mentor team members and promote strong problem-solving and communication skills.

• Support a culture of learning, accountability, and responsible innovation.

What you bring:

• 7–10 years of experience in strategy, innovation, consulting, or a related field.

• Experience in investments or pensions is an asset.

• Experience leading cross-functional initiatives from planning through execution.

• Experience developing business cases and supporting the launch of new initiatives.

• Understanding of strategic risk and scenario planning.

• Experience working on AI or technology-enabled initiatives is an asset.

• Graduate degree (MBA or equivalent) preferred.

• Experience presenting to senior leaders and facilitating group discussions.

• Experience mentoring or developing others.

• Strategic Thinking – Breaks down complex issues into clear choices and action plans.

• Innovation Leadership – Moves ideas from concept to launch using structured testing and learning.

• Risk Awareness – Considers uncertainty and risk when making recommendations.

• Execution – Delivers high-quality work on time with clear milestones.

• Analytical Skills – Uses data and research to support decisions.

• Partnerships – Builds strong relationships and works effectively across teams and with external partners.

• Communication – Creates clear presentations, reports, and strategic narratives for senior leaders and the Board.

• Leadership – Sets high standards, supports others’ development, and encourages accountability and learning.