We'rerevolutionizing how Canadians access insurance and wealth solutions by building a platform that lets people buy products the way they want to: online in minutes orvirtually viaa team of trusted, licensed Advisors. We'renot playing it safe.We'rebuilding with AI and creating omnichannel experiences — at the speed customers now expect.Youleadthe squad. Yourteam's success is your success.As Engineering Manager,you'reaccountable 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'reaccountable for how work gets done—sprint execution, code quality, team health, and delivery commitments.You'llleadthesquad, 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 andmaintaina 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 yourcommitments.You'reshipping features that drive business outcomes—lead conversion, advisor productivity, straight-through processing rates.Who You Are ?Experienced engineer ready to lead people or current EngineeringManagerfrom a product-focused tech companyStartup mindset —you know how to ship fast and iterate based on dataComfortable balancing hands-on technical work with managementStrong at sprint planning, estimation, and execution in an Agile environmentComfortablehaving 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 whilemaintaininghigh throughputWhat You Bring7+ 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-onexpertisewith Java, React (or other similar up-to-date 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.The RoleWe'rerevolutionizing how Canadians access insurance and wealth solutions by building a platform that lets people buy products the way they want to: online in minutes orvirtually viaa team of trusted, licensed Advisors. We'renot playing it safe.We'rebuilding with AI and creating omnichannel experiences — at the speed customers now expect.Youleadthe squad. Yourteam's success is your success.As Engineering Manager,you'reaccountable 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'reaccountable for how work gets done—sprint execution, code quality, team health, and delivery commitments.You'llleadthesquad, 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 andmaintaina 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 yourcommitments.You'reshipping features that drive business outcomes—lead conversion, advisor productivity, straight-through processing rates.Who You Are ?Experienced engineer ready to lead people or current EngineeringManagerfrom a product-focused tech companyStartup mindset —you know how to ship fast and iterate based on dataComfortable balancing hands-on technical work with managementStrong at sprint planning, estimation, and execution in an Agile environmentComfortablehaving 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 whilemaintaininghigh throughputWhat You Bring7+ 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-onexpertisewith 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.Disclaimer:
AI may be used in evaluating candidates.
This posting is for an existing vacancy.
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📌 Engineering Manager (Winnipeg)
🏢 S.I. Systems
📍 Winnipeg