Sr. Director, Digital Strategy

Locations: Toronto, Ontario, Canada

Time Type: Full time

Posted on: Posted 7 Days Ago

Job Requisition ID: JR101735

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

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

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

• Access to an annual wellness reimbursement program for health and wellness-related expenses for permanent and temporary employees

• 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 of Digital Strategy and Transformation plays a pivotal leadership role within the Plan Operations division at HOOPP. Reporting directly to the VP of Product & Projects, this position is responsible for driving the evolution of HOOPP’s digital strategy for Plan Administration with an enhanced focus on member-centric digital capabilities. The Senior Director will provide oversight, direction, and guidance to digital enablement that increases member engagement with HOOPP and promotes the value of HOOPP with members and Employers. This role will drive digital innovation, enhance operational effectiveness, and position HOOPP plan administration for future success in the digital age.

The ideal candidate will possess a strong background in digital strategy, change management, and operational excellence within the financial services or pension industry.

What you will do:

Digital Strategy Development & Planning

• Evolve the development and implementation of the comprehensive digital transformation strategy that aligns with HOOPP’s overall business goals and objectives.

• Leverage expertise in the pension business to inform strategic decisions related to digital strategy and service experience ensuring alignment and enforcement of HOOPP’s member service model

• Plan, socialize, and implement new strategies, while assessing and enhancing current digital strategic capabilities.

• Conduct comprehensive market research to assess customer needs and insights, informing digital initiatives.

• Explore opportunities to leverage AI and automation for internal processes and external self-service.

• Stay informed about AI trends and technologies, to champion appropriate business enablement of features and functions as appropriate for the pension industry, and HOOPP’s risk appetite

Strategic Leadership and Collaboration

• Lead and influence senior leadership to identify and align digital opportunities with overall business strategy, and to define digital vision and roadmap

• Support VP, Product & Projects in setting the overall direction of the Product team, and providing oversight to digital programs/projects in the portfolio from initiation and planning through delivery and implementation

• Collaborate with Product, Program Management, IT, Marketing, and other stakeholders in Plan Operations to drive digital initiatives and ensure seamless integration of digital solutions.

• Work closely with IT partners to mitigate risks associated with digital transformation, cybersecurity, and data privacy

• Establish strong decision-making processes, outlining procedures and frameworks for executing digital strategy through prospective digital project actions up to 1 – 2 years in advance.

• Foster relationships with external peer plans, vendors, and industry experts to stay informed about industry trends and emerging technologies.

• Oversee the selection, implementation, and optimization of digital tools and features and ensure successful adoption and utilization of new technologies across the teams.

Digital Channel Optimization and Performance Management:

• Lead and oversee the evolution of the HOOPP Member Portal and other member-centric digital channels, ensuring interactions remain user-friendly, efficient, and aligned with member expectations that promote engagement

• Lead the execution of the transactional digital roadmap for key member events, ensuring that all high-volume events are available online

• Collaborate with cross-functional teams in Plan Operations (e.g. Plan Services, Plan Design & Policy, Actuarial), Marketing, and IT to enhance digital features, functionality, and personalization.

• Lead the strategy and implementation of internal automation for business processes and controls monitoring, optimizing value to plan administration

• Develop and execute strategies to improve all digital channels (web, mobile, email, etc.) and drive member engagement through targeted content, seamless navigation, and personalized experiences.

• Identify and mitigate potential risks associated with digital transformation projects and ensure compliance with regulatory requirements and data security standards. Leverage data analytics to inform decision making, and establish KPIs and performance metrics to track progress and evaluate the success of digital initiatives.

• Monitor progress of digital initiatives and programs, identify areas for improvement, and adjust strategies as needed.

Change Management

• Develop and implement effective strategies to manage organizational change leading up to and following launch of digital capabilities and features by ensuring effective communication and business readiness programs are in place to facilitate smooth transition for both internal staff and members

• Identify and analyze potential risks associated with digital projects; develop plans to mitigate these risks and minimize business disruptions

• Anticipate and manage resistance to change by consulting and coaching project teams and influencing key stakeholders and leadership to champion change efforts

• Align workforce and processes with the digital future by guiding Plan Ops in adopting new digital technologies and aligning business practices with the digital landscape

• Champion a culture of digital innovation and agility within the organization; promote a culture of continuous improvement within Plan Ops, encouraging innovation, best practice sharing, and lessons learned to drive organizational excellence.

Leadership

• Provide leadership to promote a culture of high performance and continuous improvement that values learning, operational efficiency, and a commitment to quality.

• Provide direction, clearly communicating the objectives and goal setting.

• Lead the team in communicating a consistent view of how HOOPP operates as an organization, its core values and strategic plan to stakeholders to facilitate strong relationships.

• Mentor and develop direct reports using a supportive and collaborative approach on a consistent basis.

What you bring:

• A proven innovative thinker and problem solver; brings a big-picture perspective – the ability to see how all the pieces fit together and contribute to the achievement of broader organizational objectives; a client service orientation, strong business acumen, and judgment

• Customer-centric outlook with a focus on balancing customer satisfaction with expense management

• Results-oriented and proficient in the development and presentation of business cases and implementation plans.

• Ability to influence and negotiate up, down, and across to successfully adapt to changes that impact the needs of the business.

• Effective communication skills, both written and verbal, with all levels of internal and external stakeholders; Ability to convey and position complex financial information in a clear and compelling manner.

• Analytical mindset with the ability to solve complex problems and ability to translate information into actionable insights

• Very strong understanding of technology and data since the HOOPP service model is predicated on using technology as the primary support mechanism for delivering personal service, value, and education to members and employers

• Bachelor’s degree in Business Administration, Marketing, or a related field. Master’s degree preferred.

• Minimum of 10 years of managing digital experience, including managing large-scale initiatives from business case development through implementation

• Proven track record in digital strategy, transformation, and leadership roles.

• Experience in the Canadian/U.S. pension industry or financial services is highly desirable.

• 8-12 years work experience at a senior level in Product development, Strategy, and/or Operations with experience in managing large teams and strategic initiatives

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 460,000 members at more than 670 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 2023 our net assets reached $112.6 billion and our funded status remained strong and stable at 115%.

HOOPP's core values - professional, accountable, collaborative, 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.