Manager, Technology Portfolio Planning

Job ID : 7363
Category : Technology Solutions
Brand : Definity
Regular/Temporary : Regular
Fulltime/Parttime : Full Time
Location : Toronto, Canada
Posting Range : $77,700 - $157,000

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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 Manager, Technology Portfolio Planning is a critical contributor to Technology Solutions (TS) operations and planning. In the role, you will lead planning activities to support business case development, technology intake / demand management, and estimation processes for our strategic platforms and business-aligned applications. You will partner closely with technology and business leadership to proactively design and assess opportunities to deliver business benefits. This role is a unique opportunity to shape our technology direction and long-term strategic planning at Definity, while also ensuring alignment with overall TS Strategy and Architecture. In addition to planning, you will lead proof-of-concept and discovery intake to identify and assess new technology capabilities (e.g., GenAI) to enable future business use cases.

Strategy & Portfolio Management:

  • Lead TS intake requests, ensuring that business cases are developed within estimation guidelines, architecture strategy, and value management practices.
  • Execute on estimation framework and processes to develop business case projects to support capital planning and prioritization.
  • Support Director, Portfolio Planning with outlining platform architecture direction and strategy as part of the Portfolio planning cycle and on-going multi-year roadmap updates.
  • Support TS senior leadership with articulating intake and portfolio planning performance at Quarterly Business Reviews and applicable TS Steering Committees 
  • 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 requests, 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 identify technology risk for upcoming business and technology projects, strategies, and roadmaps.
  • Partner with executive sponsors to evolve strategic initiatives into business cases.
  • Ensure that TS solutions align to Enterprise Architecture strategy and long-term 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


  • University degree or college diploma in business administration, engineering, computer science, information systems, or a related discipline
  • 5+ years of experience in financial services across technology delivery and strategy functions
  • 5+ years of hands-on experience developing business cases to support planning and decision making
  • 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
  • Demonstrated ability to effectively lead a team in delivering timely and high-quality outputs

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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