COBRA and Direct Billing Manager

Alera Group, Inc.; Boston (MA); Remote; USD 55,000 - 70,000; Full time

Job summary

An established industry player is seeking a COBRA and Direct Billing Manager for a remote position. This role involves managing client relationships, overseeing implementations, and ensuring compliance with COBRA regulations. You will act as a trusted advisor, providing strategic guidance and support to clients while collaborating with internal teams to optimize service delivery. If you have a strong background in HR technology and client service, this is an exciting opportunity to make a significant impact in a dynamic environment.

Benefits

Medical Insurance

Dental Insurance

Life Insurance

Disability Insurance

401k

Generous Paid Time Off

Qualifications

• 3+ years in COBRA, Direct Billing, or HR technology with a client service focus.
• Recognized Subject Matter Expert in the WEX platform.

Responsibilities

• Own the full lifecycle of assigned clients, ensuring a proactive client experience.
• Oversee implementations, renewals, and ongoing client support.

Skills

Client Service

Communication Skills

Project Management

COBRA Compliance

Relationship Building

Education

Bachelor’s degree in Business

Bachelor’s degree in Human Resources

Bachelor’s degree in Information Systems

Tools

WEX platform

CRM

Zoho

Job description

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Overview

Alera Group, founded in 2017 and now the 15th largest broker of US business, is looking for a COBRA and Direct Billing Manager. This is a remote position!

We are passionate about our clients’ success in Employee Benefits, Property and Casualty Insurance, Retirement Plan Services, and Wealth Services. Our nationwide network of offices allows us to combine national resources with local service.

Responsibilities

1. Own the full lifecycle of assigned clients, ensuring a proactive, consultative, and strategic client experience that drives retention and long-term success. Act as a trusted advisor by guiding clients through best practices, platform enhancements, and strategic planning. Participate in quarterly strategy reviews, annual stewardship meetings, and health checks to strengthen relationships and reduce churn.
2. Oversee implementations, renewals, and ongoing client support. Coordinate project plans and deliverables during onboarding, work with internal teams to meet go-live dates, and conduct post-launch system audits to optimize platform performance.
3. Configure and test the WEX platform with internal teams. Ensure platform accuracy and compliance through QA testing before launches and enrollments. Finalize QA validation to ensure readiness and regulatory compliance.
4. Serve as the escalation point for resolving complex client issues, conducting root-cause analysis, and implementing preventative measures. Manage escalations, partner with the Associate Director, and use data to proactively address recurring challenges.
5. Provide training on WEX functionality, processes, and system enhancements. Oversee system administrator training and maintain updated documentation in Trainual.
6. Collaborate with internal teams to ensure seamless service delivery and identify growth opportunities through upselling and cross-selling strategies.
7. Maintain accurate client records in CRM and Trainual. Document best practices, FAQs, and updates to ensure consistency. Identify workflow efficiencies and automation opportunities.

Qualifications

1. Minimum of 3+ years in COBRA, Direct Billing, or HR technology, with a strong client service background. Bachelor’s degree in Business, Human Resources, Information Systems, or related field preferred.
2. Recognized Subject Matter Expert in the WEX platform, with certifications and ongoing engagement in training and product updates.
3. Deep understanding of COBRA compliance, regulatory requirements, and industry best practices.
4. Strong communication and relationship-building skills, with the ability to influence and educate clients.
5. Ability to manage multiple projects in a dynamic environment, utilizing tools like CRM and project management platforms (e.g., Zoho).

Benefits

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

The salary range is $55,000 to $70,000, depending on experience.

We are an equal opportunity employer. All applicants will be considered regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, veteran, or disability status.

California residents should review the California Consumer Privacy Act before applying.