Director, Technology Portfolio Planning

Job ID : 7313
Category : Technology Solutions
Brand : Definity
Regular/Temporary : Regular
Fulltime/Parttime : Full Time
Location : Toronto, Canada
Posting Range : $111,300 - $205,500

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Definity is the parent company to some of Canada’s most long-standing and innovative insurance brands, including Economical Insurance, Sonnet Insurance, Family Insurance Solutions, and Petline Insurance. Our ambition is to be one of Canada’s leading and most innovative property and casualty insurers. We can’t do that without our people, so we embrace and encourage a culture that’s collaborative, ambitious, rewarding, and empowering.

We offer a flexible, hybrid work experience where employees work from the office and virtually depending on the type of work they are doing and who they are working with. Bring your true self and be a part of our journey. It’s better here.

The Director, Technology Portfolio Planning is the functional leader for Technology Solutions (TS) strategic planning and intake management in close partnership with Definity business and TS senior leadership. The Director’s leadership, consulting skills, and strong business acumen will be key for enabling strategic business opportunities within technology & architecture strategy and corporate business goals and objectives. 

The Director will work closely with multiple stakeholder groups, such as the Enterprise Portfolio Steering Committee, Enterprise Project Management Office, Finance, Enterprise Risk, Enterprise Procurement, and Business Unit senior stakeholders to ensure Definity initiatives are initiated with well-defined benefits, cost and timeline estimates, and a solution architecture aligned with technology direction.

In addition to overseeing TS portfolio planning, the Director will also be responsible for managing technology demand and intake with business stakeholders; this includes overseeing incoming requests and managing priorities alongside in-year portfolio and operational objectives.

Strategy & Portfolio Management:

  • Lead TS workstream of corporate planning processes and TS intake, ensuring that business cases are developed within estimation guidelines, architecture strategy, and value management practices.
  • Build on the estimation framework to be able to quickly assess initiatives across key value levers, including a continuous feedback loop to improve estimation.
  • Partner with Finance and Corporate Strategy to develop value management practices, including on-going mechanisms to track technology benefits in the business / operating plan.
  • Support TS senior leadership with articulating intake and portfolio planning performance at Quarterly Business Reviews and applicable TS Steering Committees 
  • Partner with senior TS leaders to articulate platform architecture direction as a part of the Portfolio Annual Planning cycle and on-going TS multi-year roadmap discussions.
  • Partner with business and TS leaders to explore new technologies and business capabilities through 3rd party vendor solutions and strategic partnerships.
  • Support senior TS leaders with integrating business capability and business architecture practices into technology portfolio management practices.

Technology Portfolio Delivery:

  • Facilitate Technology due-diligence and requirements gathering for portfolio initiatives, including intake.
  • Be the point-of-contact for Technology Intake, including leading initiatives to support business and technology proof-of-concepts, architectural assessments, and project estimates.
  • Ensure operational processes are in place to support TS engagement between Architecture, Business-Aligned Delivery Teams, and Information Security.
  • Provide guidance, advisory services, and support to identify and quantify technology risk for upcoming business and technology projects, strategies, and roadmaps.
  • Partner with executive sponsors to evolve strategic initiatives into business cases with a supported solution architecture that is aligned with the Enterprise technology direction.
  • Partner with TS Business Management and business-aligned TS leaders to identify and forecast TS demand on resources in the outer-years.
  • Partner with business-aligned TS delivery teams to develop project and program roadmaps
  • Partner with Enterprise Architecture, Infrastructure, and Cyber-Security SMEs to ensure that all dimensions of the solution architecture are defined, accepted, and articulated
  • Build collaborative relationships with TS and Business leadership to ensure delivery readiness according to planned implementation and portfolio planning milestones
  • Ensure that TS solutions align to Enterprise Architecture strategy and long-term objectives.

Portfolio Financial Management:

  • Supports the AVP, Technology Planning & Operations to manage and report on TS financial forecasts in support of annual Portfolio and Business Planning cycles
  • Partners with TS Resource Management to develop processes that incorporate outer-year business case financial implications (e.g., SW licenses, P2P resources, environments) with TS BAU financial projections
  • Partners with Finance to ensure that planned forecast estimates are aligned with business stakeholders
  • Continuously looks for opportunities to deliver and execute the Portfolio in the most cost-effective manner to meet Definity strategic objectives

Relationship Management:

  • Collaborates with TS executives and leaders to ensure alignment of priorities, approaches, and activities
  • Collaborates with peers to achieve overall TS and Definity objectives
  • Uses influence and negotiation skills to achieve TS priorities and goals
  • Provides insight, information and recommendations related to portfolio management and technology strategy as needed to manage relationships with business leaders and stakeholders

People Management & Development:

  • Lead a growing team of planning leads and delivery managers to support the day-to-day activities and long-term objectives of Definity’s TS organization
  • Develops, coaches / mentors, and manages team and direct-report performance, ensuring achievement of both individual development goals and TS objectives
  • Responsible for the professional growth of team members in the tradition of Definity’s employee culture of diversity, inclusiveness, wellness, and job-satisfaction
  • Provides leadership to attract and retain high-quality talent
  • Promotes and supports an environment that encourages productivity, collaboration, teamwork, and a high level of professionalism
  • Promotes Definity’s Code of Business Conduct and values, and models behaviours that align to these principles


  • University degree or college diploma in business administration, engineering, computer science, information systems, or a related discipline
  • 8+ years of experience in financial services across technology delivery and strategy functions
  • 5+ years of experience in people management and team development
  • 3+ years of experience in technology management consulting
  • 3+ years of experience in project portfolio management or related roles managing / prioritizing initiatives to implement technology or business strategy
  • 3+ years of experience implementing technology platforms or solutions in financial services, including a working and practical knowledge of applying Agile and Waterfall delivery frameworks in matrix organizations
  • Experience in Canadian P&C insurance is considered an asset
  • Deep experience in independently developing and articulating / presenting technology strategy and roadmaps with C-level executives (e.g., CIO)
  • Experience in leading internal consulting engagements within technology or business organizations (e.g., current-state and target-state analysis, business architecture, technology gap analysis etc…)
  • Experience in supporting business and technology RFPs and RFIs
  • Experience in partnering with external consultants and partners to develop strategies
  • Demonstrated ability to interpret technology trends as a foundation for technology and product roadmaps
  • Ability to work closely with both business and technical resources at all levels
  • Ability to document, analyze and recommend technology solutions that improve overall business profitability and business/technology operating effectiveness
  • Strong analytical thinking and planning skills with the ability to work in a dynamic, complex, fast-paced environment, to adapt quickly and to manage changing priorities
  • Self-motivated and proactive, with respect to both managing workload and professional development
  • Demonstrated leadership ability and initiative, where independent thinking and action is a constant
  • Strong business and consultative skills to bridge the dialogue between long-term business decisions and technology architecture direction
  • “Bilingual” in business and technology communication skills with the ability to articulate the business value of technology to both technical and non-technical stakeholders
  • Collaborate across all levels while respectful to opinions and sharing of information, grounded in data and research
  • Ability to influence and effectively negotiate with stakeholders
  • Strong people management, change management, and leadership skills with the ability to build and maintain effective relationships with business partners, vendors, and TS teams
  • Demonstrated ability to effectively lead a team in delivering timely and high-quality outputs

Salary range: $111,300 - $205,500

Interested in this role, but don't meet every requirement? We encourage you to apply! We know from experience that a candidate doesn't need 100% of the qualifications listed to bring incredible value to our team. We're actively seeking diverse backgrounds and perspectives to help us make insurance better. At Definity, inclusion, diversity, and equity aren't just "nice to have" — they're essential to our success.

What's in it for you?

  • Hybrid work schedule for most roles
  • Company share ownership program
  • Pension and savings programs, with company-matched RRSP contributions
  • Paid volunteer days and company matching on charitable donations
  • Educational resources, tuition assistance, and paid time off to study for exams
  • Focus on inclusion with employee groups, support for gender affirmation surgery, access to BIPOC counsellors, access to programs for working parents
  • Wellness and recognition programs
  • Discounts on products and services

Actual salary for the role may vary depending on work location of the successful candidate and other factors including but not limited to, skills, education, experience, working conditions and the local labour market.  In addition to base pay, eligible employees may participate in various incentive plans which are paid out at the discretion of the company and subject to individual and company performance.

Go ahead and expect a lot — you deserve it.
It's better here — but don't take our word for it. Definity was named by Great Place to Work® as one of the Best Workplaces™ in Canada for women, for youth, and for inclusion.

Our inclusive work environment welcomes diversity and supports accessibility. If you require accommodation at any time during the recruitment process, please let us know by contacting [email protected].

Background checks
This role requires successful clearance of background checks (including criminal checks and leadership references).


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