Senior Technology Delivery Lead – Disability Insurance product/platform Modernization - 7008 Senior Technology Delivery Lead – Disability Insurance product/platform Modernization - 7008 Duration: 12 Months Overview: This role will be responsible for overseeing the full delivery lifecycle of the transformation program, working closely with senior business and technology stakeholders in a highly matrixed environment. The ideal candidate brings strong delivery leadership, experience in insurance and/or disability products, and a background in technology execution at scale.

Key Responsibilities - Lead the delivery of a multi-year modernization initiative for the Disability business.

- Claims and case management
- Policy administration
- Member management
- Billing and payments
- Serve as the technology sponsor, working closely with the SVP and AVP of Disability.
- Partner with business and technology teams to define and implement the migration strategy from legacy to future state.
- Drive stakeholder alignment, influence change, and serve as a thought leader in both business and technical conversations.
- Manage cross-functional delivery teams, including external vendors and offshore resources.
- Oversee program governance, delivery roadmaps, and detailed implementation planning.
- Ensure disciplined budget management, scope control, and delivery accountability.
- Collaborate with architecture, security, and infrastructure teams to ensure alignment with enterprise standards.
- Lead risk mitigation planning, quality assurance, and post-implementation reviews.

Qualifications - 10+ years of experience in technology senior leadership.

- Proven success delivering large-scale transformation programs, ideally in the insurance or financial services industry.
- Deep understanding of technology delivery models and program management frameworks.
- Familiarity with insurance platforms;

experience with Fineos or Majesco is a solid asset.





- Demonstrated ability to operate in matrixed technical environments with multiple stakeholder groups.
- Background in software development or architecture is preferred.
- Exceptional communication skills and ability to present complex ideas to business and technical stakeholders.
- Strong leadership and team management skills; able to drive delivery while fostering collaboration.
- Experience managing vendor relationships, offshoring strategies, and third-party system integration.
- Ability to work effectively with diverse teams and personalities, adapting management styles to achieve mutually beneficial outcomes.
- Track record of managing budgets and delivering within defined scope and timelines.

Senior Technology Delivery

Lead – Disability Insurance product/platform Modernization - 7008 Duration: 12 Months Location: Toronto (Hybrid, 3x/week) Overview: This role will be responsible for overseeing the full delivery lifecycle of the transformation program, working closely with senior business and technology stakeholders in a highly matrixed environment. The ideal candidate brings strong delivery leadership, experience in insurance and/or disability products, and a background in technology execution at scale.

Key Responsibilities - Lead the delivery of a multi-year modernization initiative for the Disability business.

- Consolidate legacy systems into a single core platform, encompassing:
- Claims and case management
- Policy administration
- Member management
- Billing and payments
- Serve as the technology sponsor, working closely with the SVP and AVP of Disability.




- Partner with business and technology teams to define and implement the migration strategy from legacy to future state.
- Drive stakeholder alignment, influence change, and serve as a thought leader in both business and technical conversations.
- Manage cross-functional delivery teams, including external vendors and offshore resources.
- Oversee program governance, delivery roadmaps, and detailed implementation planning.
- Ensure disciplined budget management, scope control, and delivery accountability.
- Collaborate with architecture, security, and infrastructure teams to ensure alignment with enterprise standards.
- Lead risk mitigation planning, quality assurance, and post-implementation reviews.

Qualifications - 10+ years of experience in technology senior leadership.

- Proven success delivering large-scale transformation programs, ideally in the insurance or financial services industry.
- Deep understanding of technology delivery models and program management frameworks.
- Familiarity with insurance platforms;

experience with Fineos or Majesco is a strong asset.

- Demonstrated ability to operate in matrixed technical environments with multiple stakeholder groups.
- Background in software development or architecture is preferred.
- Exceptional communication skills and ability to present complex ideas to business and technical stakeholders.
- Strong leadership and team management skills; able to drive delivery while fostering collaboration.
- Experience managing vendor relationships, offshoring strategies, and third-party system integration.
- Ability to work effectively with diverse teams and personalities, adapting management styles to achieve mutually beneficial outcomes.
- Track record of managing budgets and delivering within defined scope and timelines. Disclaimer:

AI may be used in evaluating candidates.

This posting is for an existing vacancy.

📌 Senior Technology Delivery Lead – Disability Insurance product/platform Modernization - 7008 (Toronto)
🏢 S.i. Systems
📍 Toronto