Associate Director- Spending Account Operations

OVERVIEW

Position: Associate Director - Spending Account Operations

Location: Remote. Preference to Boston, MA area.

Alera Group was founded in 2017 and has grown to become the 14th largest broker of U.S. business. We are passionate about our clients’ success in the areas of Employee Benefits, Property and Casualty Insurance, and Financial Services. With a network of offices nationwide, our commitment to collaboration allows us to offer national resources combined with local service.

• Make an Impact: Your work supports businesses and individuals in protecting what matters most.
• Grow With Us: We invest in development, mentorship, and long‑term career growth.
• The Collaborative Way: We believe in accountability, teamwork, and shared success across all offices and lines of business.
• National Strength. Local Heart: Scale, resources, and expertise - with relationships that feel personal.

Position Summary

The Associate Director, Spending Account Operations is responsible for leading a high‑performing team focused on claims processing, funding reconciliation, and data analytics for spending account programs. This role ensures the accurate and compliant administration of Health Savings Accounts (HSA), Flexible Spending Accounts (FSA), Health Reimbursement Arrangements (HRA), and Commuter Benefits, while driving operational efficiency, compliance, and client satisfaction. The Associate Director aligns department goals with broader organizational objectives, fosters cross‑functional collaboration, and ensures the successful execution of best practices and process improvements.

Additionally, this role serves as the primary liaison between internal stakeholders and external vendors, advocating for platform enhancements and ensuring seamless service delivery.

Leadership & Team Development

• Leads, manages, and develops a high‑performing team responsible for claims administration, funding reconciliation, and data analysis.
• Provides coaching, feedback, and performance evaluations through structured processes such as 15
  
  Five check‑ins, L10 meetings, and 1:1s.
• Ensures team alignment with strategic objectives, performance metrics, and compliance standards while fostering a culture of continuous learning and professional growth.

Client Experience & Retention

• Ensures best‑in‑class client service by coaching and mentoring team members to resolve client issues efficiently and proactively.
• Serves as the final escalation point for complex claims, funding discrepancies, and reporting concerns.
• Implements preventative measures to enhance client experience and optimize service delivery.
• Monitors client retention metrics and identifies areas for service enhancement and process improvements.

Operational Excellence & Compliance

• Establishes and enforces best practices for claims processing, funding reconciliation, and data integrity.
• Ensures regulatory compliance with IRS guidelines and industry standards related to HSAs, FSAs, HRAs, and Commuter Benefits.
• Works with internal teams to maintain data accuracy and process efficiency across all systems.
• Drives automation and process optimization initiatives to streamline operations and improve accuracy.

Strategic Growth & Collaboration

• Aligns department initiatives with COE’s strategic objectives, supporting revenue growth and operational efficiencies.
• Partners with Sales & Marketing to position the value proposition of spending account services.
• Collaborates with Finance & Leadership to ensure accurate revenue tracking, financial forecasting, and funding reconciliation.
• Identifies opportunities for expanding service offerings and enhancing client value through technology and service enhancements.

Performance Monitoring & Reporting

• Implements structured KPI tracking, quarterly performance evaluations, and operational reporting for senior leadership.
• Uses data‑driven insights to optimize claims administration, funding reconciliation, and overall service delivery.
• Ensures that team members are meeting or exceeding service‑level agreements (SLAs) and compliance requirements.

Vendor & Partner Liaison

• Acts as the primary liaison between internal stakeholders and…