Senior Benefits & Leave Specialist in Boston, Massachusetts at Fullscript

The Senior Benefits & Leave Specialist leads the administration and continuous improvement of employee benefits, leave of absence, and workplace accommodation programs across the U.S. and Canada. This role ensures full regulatory compliance, operational excellence, and a high-quality employee experience while proactively managing risk and partnering cross-functionally with People, Legal, Payroll, and leadership.

The role also provides oversight of worker’s compensation and U.S. and Canadian immigration processes including vendor and legal partnerships, with a focus on compliance, communication and operational effectiveness.

Benefits, Leave, and Compliance Administration

• Own end-to-end administration of U.S. and Canada benefits and leave programs.

• Ensure compliance with all applicable federal, state, and provincial regulations including COBRA, ERISA (U.S.) and ESA, WSIB, EI (Canada).

• Lead complex leave and accommodation cases (e.g., FMLA, ADA, and Canadian equivalents), ensuring a consistent and compliant interactive process.

Case Management & Employee Experience

• Manage complex and escalated leave, accommodation, and return-to-work cases in partnership with People Business Partners and leaders.

• Manage claims administration, vendor coordination and care management to support timely resolution.

• Own the end-to-end employee experience for leave and accommodations, ensuring clarity, empathy, and consistency.

• Support return to work planning and reintegration in alignment with jurisdictional requirements (state based and provincial systems).

Immigration Program Management

• Coordinate immigration processes for U.S. and Canada, including temporary work permits, LMIA applications, tracking of expirations and renewals.

• Serve as the primary point of contract for employees, providing clear communication and guidance through the immigration process.

• Partner with external legal counsel to manage case progressions and ensure compliance with legal requirements in each country.

Workers’ Compensation & Vendor Management

• Oversee U.S and Canada based workers’ compensation programs, including claims management, with the majority of the volume in the U.S.Coordinate with vendors and care providers to ensure effective case resolution and support handling and support return to work planning and reintegration.

• Monitor program performance, including claim trends, cost containment and reporting to business leaders.

Policy, Process, and Operational Excellence

• Develop, maintain, and continuously improve policies, SOPs, and documentation to ensure compliance and operational consistency.

• Lead change management and rollout of new or evolving programs, including communication strategies and cascades to ensure awareness, adoption and clarity across the organization.

• Implement scalable workflows, tools, and processes to support a distributed U.S. and Canada workforce.

• Build and enhance centralized intranet framework for benefits, leave, wellness, and wellbeing programs.

• Continuously evaluate and enhance the self-service model using employee feedback, usage data, and evolving workforce needs.

• Deep knowledge of U.S./Canada leave, benefits, and employment laws; ability to apply them with sound, defensible decision-making.

• Proven ability to lead high-risk, sensitive leave and accommodation cases end-to-end with consistency and care.

• Leverage and optimize systems including HRIS (ADP, Workday), leave management platforms (e.g. Unum) and case management tools (e.g. Asana).

• Clear, empathetic communicator who can guide employees and coach managers through complex processes.

• Ability to build, scale, and continuously improve compliant programs, policies, and workflows.

• Skilled in creating efficient, scalable processes and self-service tools that improve access and reduce friction.

• Effective cross-functional partner who can align teams and manage external vendors to deliver outcomes.