Director of Engineering

Sun Life • Waterloo, ON

4d • 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.

Requirements

• 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.
• 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.

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 so your teams can 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 the InsurTech competitors we're taking on.
• Set technical strategy and operating standards—then make it easy for your teams to ship.
• Lead Engineering Managers and individual contributors across squads.
• 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.
• We are proud to be a hybrid organization that offers our employees the choice and flexibility to work from both the office and virtually based on the needs of the business, our Clients and you!
• Several work options are available and can be discussed throughout the selection process depending on the role requirements and individual needs.

What This Job Offers

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