Client Service Specialist - Hybrid; Chicago, IL

Employee Benefits is the core of our business and at our heart we are a people-focused organization. Every day, we help over 100,000 employers give their employees peace of mind by providing health, pharmacy, long and short‑term disability, vision, dental and other insurance solutions. What makes us unique is that we can surround our clients with more services and more technology‑based tools and a team of advisors that simply cares more than anyone else.

If you want a career giving people the reassurance that they can have access to the health care they need for themselves and their loved ones, join One Digital.

The Customer Service Specialist serves as a primary point of contact for clients, employees, carriers, and internal teams, providing day‑to‑day support related to employee benefit plans. This role is responsible for resolving benefit inquiries, processing enrollment changes, and ensuring accurate administration of medical, dental, vision, life, and other benefit programs while delivering a high level of service.

• Respond to employee and client inquiries regarding benefit plans, eligibility, coverage, claims, and billing.
• Process benefit enrollments, terminations, and changes for new hires, qualifying life events, and open enrollment.
• Coordinate with insurance carriers, third‑party administrators, and vendors to resolve issues and discrepancies.
• Assist with COBRA administration, including eligibility notifications and ongoing coverage questions.
• Review and audit enrollment data to ensure accuracy across systems and carrier platforms.
• Support open enrollment activities, including employee communications and system setup.
• Maintain detailed documentation of service requests, resolutions, and follow‑ups.
• Escalate complex issues as appropriate while maintaining ownership through resolution.
• Adhere to compliance requirements and internal service standards.
• Build and maintain positive relationships with clients, employees, and internal partners.

• Strong customer service and communication skills (verbal and written).
• High attention to detail and ability to manage multiple tasks in a fast‑paced environment.
• Experience working with employee benefit plans (medical, dental, vision, life, disability, FSA/HSA preferred).
• Ability to explain complex benefit information in a clear, empathetic manner.
• Proficient in benefits administration systems and Microsoft Office applications.
• Strong problem‑solving and follow‑up skills.
• Ability to work independently and as part of a team.

• Previous experience in an employee benefits brokerage, insurance carrier, or TPA environment.
• Familiarity with benefits administration platforms (e.g., Employee Navigator, carrier portals).
• Knowledge of COBRA, eligibility rules, and qualifying life events.
• Associate’s or Bachelor’s degree preferred, or equivalent work experience.

Your base pay is dependent upon your skills, education, qualifications, professional experience, and location. In addition to base pay, some roles are eligible for variable compensation, commission, and/or annual bonus based on your individual performance and/or the company’s performance. We also offer eligible employees health, wellbeing, retirement, and other financial benefits, paid time off, overtime pay for non‑exempt employees, and robust learning and development programs.

You will receive reimbursement of job‑related expenses per the company policy and may receive employee perks and discounts. To learn more, visit:

One Digital is an equal opportunity employer. Not only as a matter of standard, but to honor and celebrate our differences. We believe that the power of ONE starts with you. We are committed to cultivating and preserving a culture that celebrates diversity, insists on equity and inclusion, and connects us. Ensuring our people feel seen, valued, respected, and supported is fundamental to our core values and business goals.

One Digital provides equal employment opportunities to all employees and applicants for employment regardless of their: veteran status, uniformed service member status, race, color, religion,…