Director of Engineering
Sun Life
Job Description
Prospris Sun Life's digital front door for Canadians—startup velocity inside a Fortune 500. We're revolutionizing how Canadians access insurance and wealth solutions by building a platform that lets people buy products the way they want to: online in minutes or virtually via a team of trusted, licensed Advisors.
We're not playing it safe. We're building with AI and creating omnichannel experiences—at the speed customers now expect.
The Role
You own outcomes—end to end.
As Director of Engineering, you own end-to-end delivery, quality, reliability, and people leadership across multiple squads. You set technical strategy and operating standards—then remove friction so your teams can ship.
You’ll operate with the velocity and accountability of a tech startup while navigating enterprise systems and stakeholders. You’ll challenge the status quo, build a high-performance engineering culture, and prove Sun Life can move as fast as the InsurTech competitors we’re taking on.
What You’ll Do
You set technical strategy and operating standards—then make it easy for your team to ship.
What Success Looks Like
Squads ship consistently and predictably with high quality, with each release driving business outcomes
You lead Engineering Managers and individual contributors across squads
Teams operate autonomously without constant escalation
Engineers are engaged, growing, and delivering impact
Leadership trusts your judgment and commitments
You’ve built a system that scales without bottlenecks
You’re accountable for engineering outcomes tied to customer growth, platform reliability, and business performance
You define and track delivery, quality, and operational metrics to ensure predictable outcomes
You partner with senior leaders on delivery and technical strategy
Who You Are
Engineering leader from product-driven companies —tech startups, scale-ups, or high-velocity digital product orgs
Strategic but execution-focused —you set direction, empower teams, and stay close to delivery, tracking key metrics and using the data to drive decision making
Strong people leader —you build culture, develop talent, hold high standards
Technically credible —can challenge architecture, review designs, mentor Staff Engineers
Thrives in ambiguity —comfortable navigating both startup chaos and enterprise constraints
Ownership mentality —accountable for outcomes, not just outputs
Startup DNA —you’ve competed against InsurTech/FinTech players and know what it takes to win
What You Bring:
10+ years of professional software engineering experience, including 5+ years in engineering leadership roles, with specific expertise with Java, React, Salesforce, and enterprise integrations
3+ years leading leaders (e.g., Engineering Managers / Team Leads) and scaling delivery across multiple squads/teams.
Demonstrated success owning end-to-end delivery for customer-facing digital products (planning → build → release → operate), with measurable outcomes.
Experience setting and running an engineering operating cadence (prioritization, planning, execution, dependencies, quality, incident learnings).
Strong track record in hiring and talent development (building high-performing teams, coaching managers, performance management).
Technical breadth and credibility: able to challenge architecture, guide technical strategy, and set standards for quality, reliability, and maintainability.
Experience partnering with Product, Design, and senior stakeholders to navigate trade-offs, risk, and timelines in a complex environment.
Why This Role
High-Impact Work: Build products that directly shape Sun Life's future, with your code reaching real users quickly
Leadership Opportunity: Lead technical direction, mentor others, and shape the engineering culture of a growing team
Autonomy and Ownership: Make decisions, drive solutions, and see the direct impact of your work
Learn and Grow Fast: Exposure to new technologies, business problems, and the full product lifecycle in a compressed timeframe
Collaborative, Innovative Culture: Work with passionate, talented people who move fast and support each other
Flexible Workstyle: In office 2-3 days per week, hybrid the rest of the week
$225k - $275k per year
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