Associate Director- Spending Account Operations

Position: Associate Director - Spending Account Operations 

Location: This role is Remote. Preference to the Boston, MA area. 

About Alera Group

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..

Why Alera Group

• 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.

Responsibilities

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 15Five 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 external technology vendors, ensuring strategic alignment and issue resolution.
• Advocates for platform enhancements and process improvements with third-party vendors.
• Ensures seamless integration and execution of spending account operations across all systems.

• Required: WEX experience
• 5+ years of experience in spending account operations (HSA, FSA, HRA, commuter benefits)
• 5+ years of experience in client success, account management, claims, or related functions
• 2+ years of leadership experience leading client-facing or operational teams
• Strong knowledge of IRS regulations and compliance related to spending accounts
• Experience working with spending account platforms and technology
• Proficiency in Excel (pivot tables, VLOOKUP) and CRM/tools (e.g., Zoho or similar)
• Proven ability to lead teams, drive process improvements, and optimize service delivery
• Strong communication and relationship management skills with the ability to resolve complex issues
• Demonstrated strategic thinking, analytical, and problem-solving skills
• Bachelor’s degree in Business, Finance, Marketing, or related field preferred

Compensation:
Salary range: $105,000 – $115,000 per year

Benefits:
Alera Group offers comprehensive benefits including medical, dental, vision, life and disability coverage, 401(k), generous PTO, and more.

Work Model:
This role is Remote. Preference to the Boston, MA area. 

Professional Development – Alera Group Academy

At Alera Group, growth isn’t left to chance. Through Alera Group Academy, we provide structured development opportunities designed to help you expand your expertise and build a meaningful career.

You’ll have access to:

• Role-specific learning paths

• Leadership development programs

• Technical and compliance training

• Industry certifications and continuing education support

• Peer learning and knowledge-sharing communities

Whether you’re deepening your technical expertise or preparing for leadership, we’re invested in helping you grow.

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.

Alera Group is committed to protecting your privacy. Please review our Privacy Policy to understand what personal information we may collect and use as part of your application process.

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