Toronto, Ontario, Canada · Hybrid
$125k–$195k/yr
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Engineering Leadership, Technical Strategy, Java, React, Enterprise Integrations
Strathcona, British Columbia, Canada · Hybrid
$80k–$128k/yr
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Business Acumen, Sales Management, Business Development, Prospecting, Recruitment
Toronto, Ontario, Canada · Hybrid
$125k–$195k/yr
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Engineering Leadership, Technical Strategy, Java, React, Enterprise Integrations
Toronto, Ontario, Canada · Hybrid
$80k–$128k/yr
Bring us your passion for digital or data analytics, and we’ll put you to work on exciting initiatives that answer the challenge: "How can we do that better?” Working with a dedicated team of energetic, forward-thinking …
Skills: Product Vision, Backlog Management, Agile Methodologies, Stakeholder Collaboration, Change Management
South Jakarta, Java, Indonesia · On-site
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Machine Learning, LLM Integration, Prompt Engineering, RAG, Python
Strathcona, British Columbia, Canada · Hybrid
$80k–$128k/yr
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Business Acumen, Insurance and Wealth Product Knowledge, Sales Management, Business Development, Prospecting
South Jakarta, Java, Indonesia · On-site
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Java, Node.js, Python, Go, RESTful API Design
South Jakarta, Java, Indonesia · On-site
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Product Ownership, Agile Delivery, Backlog Management, Sprint Planning, JIRA
South Jakarta, Java, Indonesia · On-site
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Product Management, Roadmapping, Backlog Management, User Story Writing, Agile/Scrum
South Jakarta, Java, Indonesia · On-site
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Machine Learning, LLM Integration, Prompt Engineering, RAG, Python
South Jakarta, Java, Indonesia · On-site
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Product Ownership, Agile Delivery, Backlog Management, Sprint Planning, Jira
South Jakarta, Java, Indonesia · On-site
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Product Management, Roadmapping, Backlog Management, User Story Writing, Agile/Scrum
South Jakarta, Java, Indonesia · On-site
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Java, Node.js, Python, Go, RESTful API Design
Lévis, Quebec, Canada · Hybrid
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Financial Planning, Client Relationship Management, Business Development, Communication Skills, Insurance Sales
Montreal, Quebec, Canada · Hybrid
$60k–$93k/yr
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Financial Planning, Insurance Sales, Investment Advice, Active Listening, Relationship Building
Toronto, Ontario, Canada · Hybrid
$90k–$140k/yr
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Financial Modeling, Valuation Methodologies, Financial Statement Analysis, Capital Budgeting, Microsoft Excel
Montreal, Quebec, Canada · Hybrid
$58k–$93k/yr
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Inside Sales, Lead Generation, Relationship Building, Capital Markets Knowledge, CRM Management
Montreal, Quebec, Canada · Hybrid
$58k–$93k/yr
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Inside Sales, Lead Generation, Relationship Building, Capital Markets Knowledge, CRM Management
Toronto, Ontario, Canada · Hybrid
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Medical Underwriting, Risk Assessment, Financial Analysis, Negotiation, Problem Solving
Toronto, Ontario, Canada · Hybrid
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager…
Skills: Risk Assessment, Medical Underwriting, Financial Analysis, Negotiation, Problem Solving
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The Director of Engineering owns end-to-end delivery, quality, and reliability across multiple squads while setting technical strategy. They are responsible for building a high-performance engineering culture and managing Engineering Managers to drive business outcomes.
Requires 10+ years of software engineering experience, including 5+ years in leadership and 3+ years leading other managers. Expertise in Java, React, and enterprise integrations is required, along with a proven track record of scaling digital products.
You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager to share their knowledge with you. Your leaders will inspire and help you reach your potential and soar to new heights. Every day, you'll have new and exciting opportunities to make life brighter for our Clients - who are at the heart of everything we do. Discover how you can make a difference in the lives of individuals, families and communities around the world.
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.
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
Who You Are
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
What You Bring:
10+ years of professional software engineering experience, including 5+ years in engineering leadership roles, with specific expertise with Java (or other suitable back-end languages), React (or other similar modern Javascript) and enterprise integrations. Experience with Salesforce would be an asset.
3+ years leading leaders (e.g., Engineering Managers / Team Leads) and 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 (building high-performing teams, coaching managers, performance management).
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.
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
The Base Pay range is for the primary location for which the job is posted. It may vary depending on the work location of the successful candidate or other factors. 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.
Sun Life is a leading financial services organization dedicated to helping people achieve lifetime financial security and live healthier lives. We provide a wide range of insurance and investment products and services in key markets around the world including Canada, the United States, the United Kingdom, Hong Kong, the Philippines and Indonesia. At Sun Life, we have more than 34,000 employees and 112,900 advisors worldwide. Websites: Canada www.sunlife.ca/en/ US www.sunlife.com/us/en/ Vietnam www.sunlife.com.vn Hong Kong www.sunlife.com.hk Indonesia www.sunlife.co.id Malaysia www.sunlife.com.my Philippines www.sunlife.com.ph
Offices: 18 Hung Luen Road, Hong Kong, HK · 2323 Grand Blvd, Kansas City, MO 64108, US · 1 Sun Life Park, Wellesley Hills, MA 02481, US · 5455 Avenue de Gaspe, Montreal, QC H2T 3B3, CA · 5 Công trường Mê Linh, Ho Chi Minh, Vietnam, Ho Chi Minh City 71006, VN
Sun Life is a leading financial services organization dedicated to helping people achieve lifetime financial security and live healthier lives. We provide a wide range of insurance and investment products and services in key markets around the world including Canada, the United States, the United Kingdom, Hong Kong, the Philippines and Indonesia. At Sun Life, we have more than 34,000 employees and 112,900 advisors worldwide. Websites: Canada www.sunlife.ca/en/ US www.sunlife.com/us/en/ Vietnam www.sunlife.com.vn Hong Kong www.sunlife.com.hk Indonesia www.sunlife.co.id Malaysia www.sunlife.com.my Philippines www.sunlife.com.ph
Offices: 18 Hung Luen Road, Hong Kong, HK · 2323 Grand Blvd, Kansas City, MO 64108, US · 1 Sun Life Park, Wellesley Hills, MA 02481, US · 5455 Avenue de Gaspe, Montreal, QC H2T 3B3, CA · 5 Công trường Mê Linh, Ho Chi Minh, Vietnam, Ho Chi Minh City 71006, VN
