Director of Engineering

Sun Life • Waterloo, ON

25d • CA$125,000 - CA$195,000 • Hybrid

About The Position

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

Requirements

• 10+ years of professional software engineering experience.
• 5+ years in engineering leadership roles.
• Specific expertise with Java (or other suitable back-end languages), React (or other similar modern Javascript) 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.
• Engineering leader from product-driven companies—tech startups, scale-ups, or high-velocity digital product orgs.
• Strategic but execution-focused—sets direction, empowers teams, and stays close to delivery, tracking key metrics and using data to drive decision making.
• Strong people leader—builds culture, develops talent, holds 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—has competed against InsurTech/FinTech players and knows what it takes to win.

Nice To Haves

• Experience with Salesforce would be an asset.

Responsibilities

• Own end-to-end delivery, quality, reliability, and people leadership across multiple squads.
• Set technical strategy and operating standards, then remove friction for teams to ship.
• Operate with the velocity and accountability of a tech startup while navigating enterprise systems and stakeholders.
• Challenge the status quo, build a high-performance engineering culture, and prove Sun Life can move as fast as InsurTech competitors.
• Lead Engineering Managers and individual contributors across squads.
• Ensure teams operate autonomously without constant escalation.
• Foster an environment where engineers are engaged, growing, and delivering impact.
• Build a system that scales without bottlenecks.
• Be accountable for engineering outcomes tied to customer growth, platform reliability, and business performance.
• Define and track delivery, quality, and operational metrics to ensure predictable outcomes.
• Partner with senior leaders on delivery and technical strategy.

Benefits

• In addition to Base Pay, eligible Sun Life employees participate in various incentive plans, payment under which is discretionary and subject to individual and company performance.
• Certain sales focused roles have sales incentive plans based on individual or group sales results.
• Supportive, flexible, and inclusive work environment.
• Collaborative leaders and colleagues.
• Exposure to new technologies, business problems, and the full product lifecycle in a compressed timeframe.
• Collaborative, Innovative Culture.
• Flexible Workstyle.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed