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 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 andmaintaina 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 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 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
Comfortablehaving 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 whilemaintaininghigh 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-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.
The Role
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 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 andmaintaina 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 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 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 setting
Comfortablehaving 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 whilemaintaininghigh 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-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 (Ontario)
🏢 S.i. Systems
📍 Ontario