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Sr. Benefits Specialist
Haylor, Freyer & Coon
Accounting & Finance
USD 80k-90k / year
Posted on Mar 24, 2026
OVERVIEW
RESPONSIBILITIES
QUALIFICATIONS
ADDITIONAL INFORMATION
Location Type
Remote
Benefits Specialist – Employee Benefits
Remote |
At Alera Group, we help businesses navigate risk with confidence. Our Employee Benefits teams deliver thoughtful, people-centered solutions that support organizations and the employees they serve. We’re hiring a Benefits Specialist who will play a key role in administering leave and benefits programs while ensuring compliance, accuracy, and a strong employee experience.
This role serves as a subject-matter expert in leave of absence programs and partners closely with HR, Payroll, vendors, and employees to ensure seamless, compliant operations across multiple jurisdictions.
About the Role
The Benefits Specialist is responsible for overseeing leave of absence programs while supporting core benefits administration. This role partners closely with internal teams and external vendors to ensure accurate, timely, and compliant execution of leave and benefits processes.
Success in this role looks like delivering a seamless employee experience, maintaining strong compliance across evolving regulations, and ensuring operational accuracy across leave and benefits programs.
About Alera Group
Founded in 2017, Alera Group has grown to become the 14th largest broker of U.S. business. We are passionate about our clients’ success in Employee Benefits, Property & Casualty Insurance, and Financial Services. With offices nationwide, our collaborative approach allows us to deliver national strength with local service.
If you’re someone who enjoys navigating complexity, ensuring compliance, and supporting employees through important life events, this is an opportunity to make a meaningful impact while growing your expertise in benefits and leave administration.
Why Join Alera Group
Make an impact across the organization – Support colleagues and leaders who serve clients nationwide.
Be part of a collaborative culture – Work with talented professionals across regions and business lines.
Grow your career – Access development opportunities and resources that support long-term career growth.
RESPONSIBILITIES
What You’ll Do
Leave Administration & Compliance
- Oversee and coordinate all leave of absence programs, including FMLA, ADA, disability, workers’ compensation, and state/local statutory leaves
- Serve as the primary liaison with leave, disability, and workers’ compensation vendors
- Interpret and apply federal, state, and local leave laws to ensure compliance across multiple jurisdictions
- Guide employees, managers, and HR partners on leave policies, processes, and responsibilities
- Coordinate return-to-work processes and ADA accommodations in partnership with HR and vendors
- Partner with Payroll to ensure accurate pay impacts, benefit continuation, and leave status tracking
- Monitor state leave portals and ensure compliance with required deadlines
- Audit leave data and documentation to ensure accuracy and consistency
Benefits Administration
- Support administration of health, welfare, and retirement programs, including COBRA compliance
- Manage eligibility, enrollments, and terminations with a high degree of accuracy
- Respond to employee inquiries regarding medical, dental, vision, retirement, and leave-related benefits
- Assist with retirement plan administration, including funding, audits, and reporting
- Support 401(k) inquiries including contributions and enrollment changes
- Perform audits and quality checks within HRIS and vendor systems
- Support open enrollment planning, testing, and execution
Program Support & Collaboration
- Partner with vendors, consultants, Payroll, and HR teams on data, eligibility, and compliance interpretation
- Participate in compliance and technical discussions related to leave and benefits programs
- Support new hire orientation by explaining benefits and leave offerings
- Maintain documentation standards to ensure accurate and consistent records
- Contribute to process improvements that enhance efficiency and employee experience
QUALIFICATIONS
What You Bring
Required
- 3+ years of experience supporting leave of absence programs (FMLA, ADA, disability, and state leave programs)
- Strong knowledge of federal, state, and local leave laws and regulations
- Experience working with benefits programs including health, welfare, and retirement plans
- Ability to manage multiple priorities and work independently in a fast-paced environment
- Strong analytical skills and attention to detail
- Excellent written and verbal communication skills
- Proficiency in Microsoft Office, particularly Excel
Preferred
- Experience with workers’ compensation programs
- Knowledge of ERISA and benefits compliance regulations
- Experience supporting 401(k) administration and retirement plan processes
- Background working with HRIS and vendor platforms
- Experience collaborating with Payroll, HR Business Partners, and external vendors
Core Competencies
- Compliance-focused with strong attention to detail
- Customer-first mindset with the ability to explain complex topics clearly
- Strong problem-solving and decision-making skills
- Ability to navigate change and evolving regulations
- Collaborative and team-oriented approach
Equivalent combinations of education and experience will be considered.
ADDITIONAL INFORMATION
Compensation:
Salary range: $80,000 – $90,000 per year based on expereince
Eligible for performance-based bonus: Yes
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
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 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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Location Type
Remote