Director, H&B Employer Implementation

The Director, H&B Employer Implementation and will report to the Sr. Director, H&B Implementation. This role is accountable for the implementation of reimbursement account (FSA/HRA/HSA) and COBRA programs for direct employer clients, ensuring these programs are implemented accurately, on time, and in compliance with applicable regulations. This role may lead a multi-layered team, with direct reports that act in a management role for the respective teams, as well as individual contributors, and is accountable for the overall performance, quality, and scalability of reimbursement and COBRA implementation delivery.

This position's primary responsibility is ensuring the timeliness, accuracy, and compliance of all reimbursement and COBRA program implementations for direct employer group clients. Working with the Sr. Director, Partner & Employer Onboarding, this role contributes to workforce planning, process improvement, and quality and volume monitoring specifically to reimbursement and COBRA implementation.

Duties & Responsibilities:

• Lead the team(s) accountable for implementing reimbursement account (FSA/HRA/HSA) and COBRA programs for direct employer group clients, ensuring accuracy, timeliness, and regulatory compliance.
• Manage a multi-layered organization, ensuring consistent standards and delivery quality across all teams.
• Establish and maintain standards, policies, and best practices for reimbursement and COBRA implementation to ensure consistent, high-quality, client-focused outcomes.
• Lead all reimbursement and COBRA implementation workflows, including onboarding processes, escalations, reporting, monitoring, and issue resolution to ensure accuracy, SLA adherence, and visibility.
• Oversee incident management and rapid-response processes for critical implementation issues or client escalations.
• Partner with Implementation Excellence, Operations, Technology, Product, and Compliance teams to ensure implementations are supported by scalable, compliant systems and processes.
• Ensure compliance with all applicable regulatory requirements — including IRS Section 125, COBRA continuation coverage rules, and ERISA — maintaining audit readiness and robust internal controls.
• Serve as the escalation point for critical implementation issues, escalating further to the Sr. Director, Partner & Employer Onboarding when broader organizational intervention is needed.
• Develop and execute a workforce strategy for the reimbursement and COBRA implementation organization, including staffing, capability development, succession planning, and career progression across both manager and individual-contributor levels.
• Manage budgets and vendor relationships tied to reimbursement and COBRA implementation delivery to optimize cost efficiency.
• Define, monitor, and report KPIs and SLAs specific to reimbursement and COBRA implementation performance to support strategic decision-making.
• Lead organizational change initiatives affecting reimbursement and COBRA implementation processes and technologies.
• Perform other duties as assigned.

Supervisory Responsibilities:

• Lead, mentor, and develop diverse, geographically dispersed implementation teams; foster a high-performance culture focused on accountability, innovation, and collaboration.
• Provide strategic direction and guidance directly to team members, cultivating a positive, inclusive, and results-oriented work environment.
• Manage the full talent lifecycle, including recruiting, interviewing, hiring, onboarding, and retaining high-performing employees.
• Oversee daily team workflow, ensuring efficiency, alignment with organizational goals, and delivery of implementation commitments.
• Deliver timely and constructive performance feedback, support employee development, and drive continuous improvement.
• Model organizational values, recognize excellence, and reinforce desired behaviors across the team.

Education & Experience:

• 6–10+ years of experience in implementation, customer onboarding, or operations leadership.
• 5-7 years in leadership role or managing teams
• Demonstrated success leading change management initiatives, particularly in process redesign, automation, and digital transformation.
• Experience driving process improvement and operational scalability within a regulated benefits administration environment
• Strong understanding of implementation KPIs, SLAs, and metrics-driven performance management.
• Bachelor's degree required or 10+ years of related experience, preferably in Business, Business Administration or a related field.

Skills & Abilities:

• Working knowledge of Consumer Directed Health account types (FSA, HRA, HSA) and COBRA administration, including plan design, eligibility rules, and compliance requirements under IRS Section 125, ERISA, and COBRA continuation coverage regulations.
• Strong leadership, coaching and team-building abilities.
• Excellent communication and collaboration skills across executive, staff, and internal/external stakeholders.
• High adaptability, resilience, and ability to thrive in a dynamic, fast-paced environment.
• Client-centric mindset with a focus on delivering exceptional onboarding and implementation experiences.