Technology analyst Jobs in Waterloo, ON

Job Description

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The Opportunity

Lead a transformational technology organization powering health and benefits experiences for millions. As the Assistant Vice-President (AVP), Technology Lead, you will own one of Sun Life Canada’s largest technology portfolios for health benefits claims adjudication/processing, virtual health, and online pharmacy systems.

You will lead a 250+ person technology professional organization including 5 Directors across multiple high-performing squads in a matrixed environment. This is your chance to shape strategy, drive modernization, and build a world-class engineering culture that balances breakthrough innovation with operational excellence.

You'll partner with executives across Architecture, Product, Operations, and Business to define the future of Sun Life's health technology platforms including mission-critical mainframe systems to cutting-edge digital experiences—while managing complex vendor ecosystems and driving sustainable delivery practices.

This role is highly visible, mission-critical to Sun Life Canada’s core business, strategically influential, and demands a leader who thrives in complexity.

Why This Role Matters

You'll lead a strategic inflection point for Sun Life's health benefits claims and on-line health technology organization. Leading one of Sun Life Canada’s largest technology portfolios and 250+ technology professionals, you have the scale, resources, and mandate to drive meaningful modernization while serving millions of members. This is a high-visibility opportunity to influence enterprise technology strategy, build a best-in-class engineering culture, and deliver business impact in a complex, mission-critical environment.

What You'll Own

Technology Strategy & Modernization Leadership

• Define and communicate a compelling technology vision that bridges near-term delivery with long-term platform modernization across health benefits claims, adjudication systems, online health platforms, and core systems of record.
• Lead evolution of Sun Life's health technology ecosystem—making bold build vs. buy vs. partner decisions in an extremely large technology portfolio
• Champion modern engineering practices, technology standards, and architectural excellence while actively managing technical debt in complex, non-greenfield environments
• Partner with Business, Architecture, and Enterprise Technology leaders to design resilient, scalable platforms that deliver exceptional member and sponsor experiences

Delivery Excellence at Scale

• Accountable for end-to-end delivery across multiple agile squads at varying maturity levels—driving velocity, quality, and reliability improvements
• Manage relationships with system integrators and vendors, holding partners accountable for outcomes and knowledge transfer
• Serve as the primary escalation point for critical platform and delivery issues in a mission-critical environment
• Transform delivery metrics into actionable insights and drive continuous improvement

People Leadership & Culture Building

• Lead, mentor, and develop 250+ technology professionals across 5 Director level reports and cross-functional teams
• Foster a collaborative, inclusive, execution-focused culture rooted in psychological safety and continuous learning
• Design high-performing team structures aligned with business outcomes and technical excellence
• Build and retain technical talent through coaching, career development, and hands-on leadership

Financial & Strategic Vendor Management

• Own platform budgeting, cost optimization, and capitalization decisions
• Manage strategic vendor and SI relationships to maximize delivery quality and ROI
• Drive alignment between IT spend and business value delivery

Governance & Risk Management

• Establish governance that accelerates delivery while meeting regulatory and security requirements
• Ensure platform stability, security, and effective incident/change management for mission-critical systems
• Partner with Operations on disaster recovery and business continuity for enablement platforms

Who You Are

Experience & Expertise

• 10+ years in senior technology leadership roles for very large technology portfolios, with proven success delivering complex, mission-critical systems at enterprise scale
• Deep expertise with Mainframe environments and their integration with modern and digital business-critical systems
• Track record modernizing and enabling health benefits claims / health technology platforms.
• Strong financial acumen—comfortable managing large budgets, vendor portfolios, and ROI optimization - Demonstrated ability to lead technology teams through transformation while maintaining operational excellence

Technical Credibility & Mindset

• Strong technical foundation with the credibility to challenge architecture, delivery practices, CI/CD, and engineering approaches
• Builder mentality—equally focused on fixing legacy systems, scaling capabilities, and enabling teams
• Decisive leader comfortable making clear decisions amid ambiguity and complexity
• Pragmatic, outcomes-driven thinker who balances innovation with stability
• Collaborative leader who rebuilds trust, drives momentum, and fosters transparency

Education

• Bachelor's degree in Computer Science, Engineering, or related field (MBA or advanced degree is an asset)
• Experience in regulated health, insurance or financial services is valuable

As this position is posted in several locations, we specify that bilingualism (French, English, both oral and written) is required for Quebec only as the position includes managing both French and English-speaking staff (Quebec and outside Quebec) and providing daily support to the team.

What’s in it for you?

• Great Place to Work® Certified for Most Trusted Executive Team in Canada – 2025, 2024 and 2023
• Great Place to Work® Certified for Best Workplaces in Canada - 2025
• Canada Order of Excellence for Mental Health at Work® certification from Excellence Canada. Sun Life is one of only four companies in Canada to ever receive this certification – 2024
• Top Work Places® for Remote Work – Monster Canada - 2024
• Great Place to Work® Certified for Best Workplaces in Canada – 2024 and 2022
• Great Place to Work® Certified for Best Workplaces for Women in Canada - 2024
• Flexible hybrid work model.