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 Senior Director, Enterprise Initiatives plays a pivotal role in advancing the organization’s strategic initiatives, operational effectiveness, and organizational efficiency. Supporting the Chief of Staff & Corporate Secretary and the CEO, this role serves as a central connector across the enterprise, aligning and executing high-priority projects, streamlining communication across divisions, and supporting delivery of the organization’s goals and objectives. This position provides a unique opportunity to gain enterprise-wide exposure, work closely with the CEO and senior executive team, and directly influence the execution of HOOPP’s strategic objectives. The ideal candidate is highly organized, analytical, and collaborative, with a strong ability to navigate complex issues, build relationships, and deliver results in a dynamic, fast-paced environment. What you will do: Strategic Planning & Execution: Partner with the Chief of Staff & Corporate Secretary (COS&CS) to plan and deliver initiatives that advance HOOPP’s strategy, ensuring alignment of communications, change management, leadership engagement, and execution of CEO priorities. Develop performance dashboards or reports that monitor progress on key priorities and provide actionable insights. Support leadership meetings and forums and coordinate information flow and action tracking between the Office of the CEO and the enterprise. Problem Solving & Decision Support: Identify and manage emerging issues and risks, and recommend solutions to support CEO and senior leadership decision-making. Conduct research, synthesize insights and prepare concise, high-quality briefings and summaries. Ensure that all briefing materials and communications are of the highest quality and delivered to the CEO at the right point in the decision-making process. Strategic Partnerships & Stakeholder Relations Aggregate and analyze enterprise-wide information to inform stakeholder engagement and partnership strategies, identify opportunities, and present actionable insights. Support the CEO’s stakeholder and strategic partnership engagement, ensuring alignment with organizational priorities and strategy. Serve as a trusted liaison between the Office of the CEO and external stakeholders, maintaining professional communication and supporting the development of executive messaging for meetings and partnership activities. Executive Communication & Coordination: Enable effective communication and coordination between the CEO, COS&CS, and senior leadership to ensure clarity and alignment. Collaborate with communication teams to ensure accuracy and consistency of the CEO’s external messaging, public remarks and executive communications. Prepare timely and accurate executive-level reports, briefings, and presentations for the COS&CS and the CEO. Collaborate with internal teams to plan and deliver the CEO’s all-staff meetings, town halls, off-sites, and other corporate events, supporting the development of related communications materials. Operational Effectiveness & Efficiency: Drive operational excellence by optimizing workflows, meeting structures, and follow-up processes to enhance coordination, clarity, and execution. Foster two-way communication and coordination with divisions to strengthen information flows and help teams stay aligned on the organization’s goals. What you bring: Bachelor’s degree in business administration, Finance, Management, Communications, or a related field. 10+ years of experience in a strategic, operational, or advisory capacity, ideally within financial services, consulting, government, or a pension-related organization. Proven experience managing complex, cross-functional projects and managing multiple priorities under pressure. Strong problem-solving and analytical abilities, with a strategic mindset. Exceptional written and verbal communication skills with the ability to prepare concise, executive-level narratives and materials. Experience in strategic communications, public affairs, or reputation management is an asset. Strong change-leadership and influencing skills, with the ability to align diverse stakeholders around common goals. Demonstrated ability to work in a high-stakes environment supporting senior executives. Adaptability and sound judgment in a dynamic and evolving environment. High degree of discretion, professionalism, and ability to handle confidential information. Strong interpersonal skills and a collaborative, diplomatic leadership style with the ability to influence. About HOOPP The Healthcare of Ontario Pension Plan (HOOPP) is one of the strongest and most stable defined benefit (DB) pension plans in Canada. Since 1960, HOOPP has been helping Ontario's healthcare workers build the foundation for a financially secure retirement. We take pride in being the pension plan for Ontario’s healthcare community and serve more than 478,000 members at more than 700 employers across the province. At HOOPP, we are committed to providing our members with a stable and reliable pension that starts in retirement and is paid for life. With offices in Toronto and London, we manage a global, multi-asset class investment portfolio. At the end of 2024 our net assets reached $123.0 billion and our funded status remained strong and stable at 111%. HOOPP's core values - accountable, compassionate and trustworthy - guide every interaction with our members, employers and employees. We've become one of Canada's leading pension plans by consistently challenging ourselves and embracing innovation. From our unique investment management approach to our innovative technology and thought-provoking research, we constantly seek to push the boundaries, and we do this by hiring passionate, forward-thinking people. Our high-performance culture is founded on collaboration, respect and belonging. HOOPP is an equal opportunity employer and we're proud of our diversity. We select applicants for employment solely on the basis of their qualifications. Should you require accommodation because of a disability during the recruitment and selection process, please contact our Human Resources team. We will be happy to consult with you so that arrangements can be made for reasonable accommodation.
