Remote Benefits Account Manager — Client Relations

Work Friendly; Chicago (IL); On-site; USD 85,000 - 110,000; Full time

Benefits offered by this job

Fully remote work

401(k) with employer match

Paid parental leave

Professional development budget

Licensing and designations support

Job summary

Work Friendly is seeking an Employee Benefits Account Manager to own a book of small and mid‑market clients, handling open enrollment, renewals, and compliance. This is a remote role open to the Midwest and South, with travel to Chicago as needed, reporting to the Executive Team.

You bring 3–5+ years in benefits account management, a life/health license or willingness to obtain, and strong communication and project management skills to build scalable processes and serve diverse clients.

Qualifications

• 3–5+ years of experience in employee benefits account management, benefits administration, or as a benefits broker / consultant team member.
• Active Life & Health insurance license — or willingness to obtain within 60 days of hire.
• Working knowledge of fully-insured and level-funded medical plans, ancillary lines, and self-service benefits administration platforms.
• Solid grasp of ACA, ERISA, COBRA, HIPAA, and Section 125 compliance fundamentals.
• Excellent written and verbal communication, translating jargon into plain English for employees and executives alike.
• Strong project management instincts: organized, calm under deadlines, and great at follow‑through.
• Proficiency with Microsoft 365 and comfort learning new tech.
• Experience supporting small to mid‑market employers (25–500 lives).
• Familiarity with benefit administrative systems.
• Exposure to self‑funded or level‑funded plan designs and reporting.
• GBA, CEBS, PHR, or SHRM‑CP coursework or certification.
• Experience building processes from scratch in a small, growing team.

Responsibilities

• Serve as the primary point of contact for a dedicated book of employer clients across health, dental, vision, life, disability, and voluntary benefits.
• Build trusted, long‑term relationships with our clients’ executive teams.
• Lead recurring client check‑ins, stewardship meetings, and mid‑year reviews.
• Anticipate client needs and proactively bring forward solutions, ideas, and education.
• Project‑manage the annual renewal and open enrollment cycle end‑to‑end: timelines, deliverables, communications, and on‑time delivery.
• Prepare renewal analyses, benchmarking, plan comparisons, and contribution modeling.
• Build employee‑facing materials including benefit guides, OE presentations, and enrollment communications.
• Lead virtual and (occasionally) in‑person open enrollment meetings.
• Manage carrier relationships across medical, ancillary, and supplemental lines.
• Resolve eligibility, billing, claims, and escalated service issues quickly and clearly.
• Coordinate plan implementations, mid‑year changes, and vendor transitions.
• Keep clients on top of ACA, ERISA, COBRA, HIPAA, Section 125, and state‑level compliance requirements.
• Support 5500 filings, SBC distribution, SPD updates, and required notices.
• Maintain accurate client records, plan documents, and renewal data in our management system.
• Partner with Work Friendly People Consultants to support new business.
• Contribute to building scalable account management playbooks, templates, and SOPs as our first dedicated AM.
• Share what you’re seeing (client feedback, market trends, recurring pain points) to help us improve.

Skills

Client relationship management

Communication

Project management

Microsoft 365

Benefits administration

ACA/ERISA/COBRA knowledge

Vendor management

Education

Active Life & Health insurance license

GBA/CEBS/PHR/SHRM-CP coursework or certification

Tools

Agency management systems

Benefits administration platforms

Job description

Work Friendly is seeking an Employee Benefits Account Manager to own a book of small and mid‑market clients, handling open enrollment, renewals, and compliance. This is a remote role open to the Midwest and South, with travel to Chicago as needed, reporting to the Executive Team.

You bring 3–5+ years in benefits account management, a life/health license or willingness to obtain, and strong communication and project management skills to build scalable processes and serve diverse clients.