Director, Connectivity Strategy & Operational Enablement

Sun Life • Wellesley, MA

2h • Hybrid

About The Position

Sun Life embraces a hybrid work model that balances in-office collaboration with the flexibility of virtual work. Our team members and leaders are expected to foster connection and teamwork by being present in the office at least 2 days per week. The Opportunity Sun Life's Digital Strategy organization is responsible for delivering industry-leading digital solutions by building scalable, client-focused technologies that align with strategic business objectives. The Director, Connectivity Strategy & Operational Enablement plays a pivotal leadership role in defining, prioritizing, and ensuring the delivery of value for all EDI and API connectivity solutions across our ecosystem. This critical position is accountable for the value delivered by data connectivity across value streams, working closely with Sales, Operations, Legal, Compliance, Claims, Underwriting, Product, Account Management, and IT. By enabling seamless connectivity that enhances the experience for brokers, employers, and their employees, this role directly supports Sun Life's digital client journey ambition and growth objectives. You will set the vision and strategic direction for enterprise data connectivity with direct accountability for how API and EDI capabilities enable value delivery across Sun Life's value streams. You will have the authority to make key strategic and investment decisions that shape the effectiveness, scalability, and impact of API and EDI partnerships. This position requires a seasoned leader who can balance strategic platform thinking with hands-on leadership, driving innovation while maintaining strong, trust-based relationships with internal partners and external ecosystem participants. You will operate independently to develop and execute strategic plans aligned to enterprise objectives while leading transformational change across processes, operating models, and organizational mindset.

Requirements

• 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
• Proven experience leading people, driving change, and creating a high-performance culture
• 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

Nice To Haves

• Master's degree in business management or technical field
• Benefits/HR technology or connectivity technology (EDI/API) expertise
• Previous experience in the insurance industry
• Demonstrated innovation and digital transformation leadership

Responsibilities

• 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
• Simplify connectivity for ecosystem participants to increase broker confidence
• Gather feedback from clients, brokers, technology partners, and internal stakeholders
• Facilitate cross-functional collaboration among Lean-Agile leaders and value stream teams
• Leverage internal partnerships to anticipate needs and deliver scalable solutions
• Identify and drive process improvements aligned with connectivity strategy
• Lead organizational change initiatives supporting platform-oriented, value-driven API and EDI delivery
• Establish and institutionalize best practices across the organization
• Direct people leadership, performance management, and budget planning

Benefits

• 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 that supports career growth

What This Job Offers

• Job Type: Full-time
• Career Level: Director