Director of Engineering

Sun Life•Waterloo, ON

10d•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. The Role You own outcomes—end to end. As Director of Engineering, you own end-to-end delivery, quality, reliability, and people leadership across multiple squads. You set technical strategy and operating standards—then remove friction so your teams can ship. You'll operate with the velocity and accountability of a tech startup while navigating enterprise systems and stakeholders. You'll 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. For candidates with these preferred skills, exceptions beyond the usual salary range below may be possible. What You'll Do You set technical strategy and operating standards—then make it easy for your teams to ship. What Success Looks Like Squads ship consistently and predictably with high quality, with each release driving business outcomes You lead Engineering Managers and individual contributors across squads Teams operate autonomously without constant escalation Engineers are engaged, growing, and delivering impact Leadership trusts your judgment and commitments You've built a system that scales without bottlenecks You’re accountable for engineering outcomes tied to customer growth, platform reliability, and business performance You define and track delivery, quality, and operational metrics to ensure predictable outcomes You partner with senior leaders on delivery and technical strategy

Requirements

10+ years of professional software engineering experience.
5+ years in engineering leadership roles.
Specific expertise with Java (or other suitable back-end languages).
Specific expertise with React (or other similar modern Javascript).
Specific expertise with enterprise integrations.
3+ years leading leaders (e.g., Engineering Managers / Team Leads).
Experience 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.
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.
Engineering leader from product-driven companies—tech startups, scale-ups, or high-velocity digital product orgs.
Strategic but execution-focused—you set direction, empower teams, and stay close to delivery, tracking key metrics and using the data to drive decision making.
Strong people leader—you build culture, develop talent, hold high standards.
Technically credible—can challenge architecture, review designs, mentor Staff Engineers.
Thrives in ambiguity—comfortable navigating both startup chaos and enterprise constraints.
Ownership mentality—accountable for outcomes, not just outputs.
Startup DNA—you've competed against InsurTech/FinTech players and know what it takes to win.

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.
Remove friction so teams can ship.
Operate with the velocity and accountability of a tech startup while navigating enterprise systems and stakeholders.
Challenge the status quo and build a high-performance engineering culture.
Lead Engineering Managers and individual contributors across squads.
Ensure teams operate autonomously without constant escalation.
Ensure engineers are engaged, growing, and delivering impact.
Build a system that scales without bottlenecks.
Be accountable for engineering outcomes tied to customer growth, platform reliability, and business performance.
Define and track delivery, quality, and operational metrics to ensure predictable outcomes.
Partner with senior leaders on delivery and technical strategy.
Hire and develop talent, build high-performing teams, coach managers, and manage performance.
Guide technical strategy and set standards for quality, reliability, and maintainability.
Partner with Product, Design, and senior stakeholders to navigate trade-offs, risk, and timelines in a complex environment.

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.
Diversity and inclusion have always been at the core of our values at Sun Life.
A diverse workforce with wide perspectives and creative ideas benefits our Clients, the communities where we operate and all of us as colleagues.
We welcome applications from qualified individuals from all backgrounds.
Persons with disabilities who need accommodation in the application process, or those needing job postings in an alternative format, may e-mail a request to [email protected].
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.
We may use artificial intelligence to support candidate sourcing, screening, interview scheduling.
We thank all applicants for showing an interest in this position.
Only those selected for an interview will be contacted.
Make life brighter
Working in Tech, you will have the opportunity to have widespread impact across all levels of the organization.
By helping us find better and smarter ways of doing things, you will make a positive impact in the lives of our clients and colleagues and contribute to our meaningful purpose.
Shape the future
In Tech at Sun Life, you will be at the forefront of our transformation.
You will apply your curious mind, bold thinking, and creativity to evolve our offering and processes and shape the future of our industry.
You will be empowered to push boundaries and explore new ways of doing things to drive positive change.
Your unique perspective is exactly what we’re looking for.
Join a top employer for a brighter future.
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