Director, Connectivity Strategy – Operational Enablement

Sun Life

Director of Connectivity Strategy leading EDI and API connectivity initiatives for Sun Life’s digital strategy. Collaborates across teams to drive innovation and strategic direction in connectivity solutions.

Posted 6/13/2026full-timeWellesley Hills • Connecticut, Massachusetts, Montana, Wisconsin • 🇺🇸 United StatesLead💰 $137,900 - $206,900 per yearWebsite

About the role

Key responsibilities & impact

Partner with Lean-Agile leaders to align connectivity strategy with value stream and enterprise objectives
Define and own the vision, outcomes, and long-term direction for API and EDI value delivery
Articulate a compelling strategic vision and build alignment across business and technology leaders
Engage executive leadership and major clients to influence enterprise strategy
Own and track OKRs, KPIs, and performance metrics for the connectivity value stream
Analyze results and develop action plans to improve value delivery and adoption
Identify and evaluate strategic business opportunities aligned with enterprise priorities
Identify, manage, and mitigate business risks, dependencies, and constraints
Ensure reliable and efficient value stream delivery while maintaining client experience and operational stability
Deploy resources across teams to resolve issues and sustain delivery
Drive enterprise EDI and API strategy across Sun Life's Group Benefits ecosystem
Develop scalable, repeatable connectivity models that support seamless integration with the benefits’ technology landscape
Gather feedback from clients, brokers, technology partners, and internal stakeholders
Lead organizational change initiatives supporting platform-oriented, value-driven API and EDI delivery

Requirements

What you’ll need

7+ years of experience in a senior management or business strategy role
10+ years of experience in the group insurance business with focus on connectivity, technology, or digital solutions
Bachelor’s degree in business management or technical field (or equivalent years of experience in group insurance)
Strong leadership, management, and strategic planning skills
Excellent communication, negotiation, and problem-solving skills
Experience with agile development practices and tools such as Jira and Confluence
Strong relationship management and analytical skills
Demonstrated ability to influence and develop effective internal and external business relationships
Excellent verbal, presentation, and written communication skills
Ability to work in a deadline-oriented environment with multiple priorities
Ability to work independently with minimal supervision
Demonstrated strategic thinking and execution capabilities.

Benefits

Comp & perks

Generous vacation and sick time
Market-leading paid family, parental and adoption leave
Medical coverage
Company paid life and AD&D insurance
Disability programs
Partially paid sabbatical program
401(k) employer match
Stock purchase options
Employer-funded retirement account
Flexible, inclusive and collaborative work environment

ATS Keywords

✓ Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

API developmentEDI deliverystrategic planningperformance metricsvalue stream analysisbusiness risk managementchange managementconnectivity strategydigital solutionsagile development practices

Soft Skills

leadershipcommunicationnegotiationproblem-solvingrelationship managementanalytical skillsstrategic thinkingexecution capabilitiesorganizational skillsindependent work