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. You lead the squad. Your team's success is your success.As Engineering Manager, you're accountable for a single squad's delivery, people development, and execution quality. You balance hands‑on technical contribution with people leadership. You translate product requirements into executable work, own sprint commitments, and ensure your squad is healthy, productive, and shipping at startup velocity.You're accountable for how work gets done—sprint execution, code quality, team health, and delivery commitments. You'll lead the squad, working closely with Product Directors to drive business outcomes.What You'll Do?
Lead sprint execution and delivery commitments
with full accountabilityTranslate product requirements
into clear, executable engineering workDirectly manage developers —hiring, own their performance, growth, engagement, and career developmentEnforce engineering standards and code quality
within your squadStay technically credible —you code when needed and lead technical discussionsBuild and maintain a healthy squad culture
aligned with Accelerator principlesRemove blockers and manage dependencies
with other squads, enterprise teams,



and vendorsOwn day‑to‑day delivery coordination
with Product, Design, and other squadsBalance technical debt with feature delivery —you make the trade‑offsOperate with startup velocity —fast iterations, continuous deployment, data‑driven decisionsWhat Success Looks Like?
Your squad delivers predictably and at high velocity. Engineers are growing and engaged. Code quality is consistently high. The team collaborates well. Product and stakeholders trust your commitments. You're shipping features that drive business outcomes—lead conversion, advisor productivity, straight‑through processing rates.Who You Are?
Experienced engineer ready to lead people
or current Engineering Manager from a product‑focused tech companyStartup mindset —you know how to ship quick and iterate based on dataComfortable balancing hands‑on technical work with managementStrong at sprint planning, estimation, and execution
in an Agile environmentComfortable having tough conversations
about performance, growth, and accountabilityDetail‑oriented without losing sight of business outcomesAble to context‑switch
between code reviews, 1:1s, and stakeholder managementProtective of your team's time and focus




while maintaining high throughputWhat You Bring
7+ years of professional software engineering experience, including 2+ years in an Engineering Manager (or equivalent team leadership) role.Experience leading a single squad/team end‑to‑end (delivery, quality, reliability, and team health), with clear examples of outcomes.Demonstrated ability to run team‑level execution rituals (planning, sprint/flow management, dependencies, release coordination) and improve delivery predictability.Experience hiring, onboarding, and developing engineers (coaching, feedback, performance conversations)Technical credibility to guide design and implementation: comfortable with architecture discussions, code/design reviews, and raising the engineering quality bar.Proven partnership with Product and Design to shape scope, manage trade‑offs, and communicate progress/risks clearly.Why This Role?
High-Impact Work: Build products that directly shape Sun Life's future, with your code reaching real users quicklyLeadership Opportunity: Lead technical direction, mentor others, and shape the engineering culture of a growing teamAutonomy and Ownership: Make decisions, drive solutions, and see the direct impact of your workLearn and Grow Fast: Exposure to new technologies, business problems, and the full product lifecycle in a compressed timeframeCollaborative, 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
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📌 Senior Manager, Data Security Automations & Engineering (Global Security) (Winnipeg)
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