Associate Director, Spending Account Operations

Overview

Alera Group is looking for an Associate Director, Spending Account Operations. You’ll be at the helm of a talented group, driving innovation and delivering exceptional results together. Alera Group was founded in 2017 and has grown to become the 14th largest broker of US business. We are passionate about our clients’ success in the areas of Employee Benefits, Property and Casualty Insurance, Retirement Plan Services, and Wealth Services.

With a network of offices nationwide, our commitment to collaboration allows us to offer national resources combined with local service.

• Leads and mentors a high‑performing team overseeing claims administration, funding reconciliation, and data analysis; provides structured coaching, feedback, and evaluations through 15
  
  Five check-ins, L10 meetings, and 1:1s to drive engagement and growth
• Ensures team alignment with organizational goals, KPIs, and compliance standards while fostering accountability and continuous improvement
• Coaches staff to deliver proactive, high-quality client service; serves as final escalation point for complex claims and funding issues; identifies and implements improvements to enhance satisfaction and retention
• Establishes best practices for claims processing, funding reconciliation, and data integrity; ensures adherence to IRS and industry regulations for HSAs, FSAs, HRAs, and Commuter Benefits
• Partners across teams to streamline workflows, drive automation, and improve accuracy, efficiency, and scalability of operations
• Works with Sales, Marketing, Finance, and Leadership to support revenue growth, forecast accuracy, and enhanced service offerings through technology and process innovation
• Oversees KPI tracking, operational reporting, and vendor relationships; advocates for system enhancements and ensures seamless integration and execution across all platforms

• Bachelor’s degree in Business, Finance, Marketing, or a related field preferred
• Minimum of 5 years of experience in spending account administration, client success, account management, claims, or related areas, with leadership experience
• Experience with spending account technology platforms. WEX experience required
• Subject matter expertise in IRS regulations and compliance related to HSAs, FSAs, HRAs, and Commuter Benefits
• Proficiency in CRM and project management tools (e.g., Zoho or similar), with strong Excel skills (VLOOKUP, pivot tables, data validation)
• Demonstrated experience leading client‑facing teams, driving process improvements, and optimizing service delivery
• Excellent communication and relationship management skills, with the ability to resolve complex issues and collaborate cross‑functionally
• Strong strategic thinking, analytical, and problem‑solving abilities with a focus on compliance, client satisfaction, and operational success

This job is fully remote – preference to the Boston area.

Alera Group offers comprehensive benefits to our colleagues, including medical, dental, life and disability insurance, 401k, generous paid time off and much more.

Salary range is $120K to 140K per year.

We’re an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status, or any other protected class.

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