Engineering Jobs in York, ON

Job Description

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The Role

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 accountability
• Translate product requirements into clear, executable engineering work
• Directly manage developers—hiring, own their performance, growth, engagement, and career development
• Enforce engineering standards and code quality within your squad
• Stay technically credible—you code when needed and lead technical discussions
• Build and maintain a healthy squad culture aligned with Accelerator principles
• Remove blockers and manage dependencies with other squads, enterprise teams, and vendors
• Own day-to-day delivery coordination with Product, Design, and other squads
• Balance technical debt with feature delivery—you make the trade-offs
• Operate with startup velocity—fast iterations, continuous deployment, data-driven decisions

What 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 company
• Startup mindset—you know how to ship fast and iterate based on data
• Comfortable balancing hands-on technical work with management
• Strong at sprint planning, estimation, and execution in an Agile environment
• Comfortable having tough conversations about performance, growth, and accountability
• Detail-oriented without losing sight of business outcomes
• Able to context-switch between code reviews, 1:1s, and stakeholder management
• Protective of your team's time and focus while maintaining high throughput

What 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.
• Hands-on expertise with Java, React (or other similar modern Javascript) and enterprise integrations. Experience with Salesforce would be an asset.
• 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 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