Prospr is 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. 

For candidates with these preferred skills, exceptions beyond the usual salary range below may be possible. 

What You'll Do 

You set technical strategy and operating standards—then make it easy for your teams 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 (or other suitable back-end languages), React (or other similar modern Javascript) and enterprise integrations. Experience with Salesforce would be an asset.

• 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