Senior Benefits Project Manager – Lake Barrington, IL
$90,000 – $115,000 annually (based on experience)
Full benefits include health, dental, FSA/HSA, vision, 401(k) matching, life insurance, PTO, bonus incentives, as well as an onsite gym.

WHO WE ARE:

Union One is the largest union benefits administrator in the country. We specialize in delivering tailored insurance and voluntary benefit solutions to unions and their members nationwide. Our mission is simple: to make benefits easier, more accessible, and more effective for working people. We’re growing fast and looking for someone who’s ready to help us raise the bar.

QUALIFICATIONS:

• Bachelor’s degree in Business or a related field.
• A minimum of 5 years of experience in group benefits, voluntary benefits, insurance brokerage, or benefits implementation.
• Experience working with or for Group Life and Disability Insurance Carriers; ideally with labor unions or multi-employer plans.
• Proficiency in Microsoft Office Suite, particularly Excel, PowerPoint, Outlook, and Word.
• Hands-on experience with enrollment platforms, benefits websites, and CRM systems.
• A background in SaaS, Insurtech, or HR technology—and familiarity with eligibility file feeds—is strongly preferred.
• Clear communicator and natural collaborator with a strong foundation in project management, including implementations and renewals.
• Comfortable managing multiple projects and deadlines, ideally within the context of open enrollments, employee communications, and vendor coordination.
• Must currently hold or be willing and eligible to obtain Life and Health Insurance Licenses in the state of Illinois, with no pending investigations or prior disciplinary actions.
  Job Type: Full-time
  Pay: $90,000.00 - $115,000.00 per year

Benefits:

• 401(k) matching
• Dental insurance
• Flexible spending account
• Health insurance
• Health savings account
• Life insurance
• Paid time off
• Vision insurance

License/Certification:

• Health and Life Insurance License (Preferred)

Ability to Commute:

• Lake Barrington, IL 60010 (Required)

Work Location: In perso

WHAT YOU’LL DO:

This role is all about ownership. As our Senior Benefits Project Manager, you’ll be the lead on all new group insurance plan rollouts—from initial onboarding to ongoing support after launch. You’ll work cross-functionally with clients, internal teams, and vendor partners to bring each plan to life, making sure every piece is aligned and every deadline is met.
Our ideal candidate will bring valuable experience working with group life and disability carriers, will be familiar with labor unions or multi-employer plans, and would have a background in SaaS, Insurtech, or HR Technology. This role requires someone who is a natural collaborator that thrives in cross-functional settings and loves building better processes.
If you want to be a key player in building something transformative—we’re already in motion and gaining altitude fast as we redefine what’s possible within the insurance space. If that sounds like the kind of journey you want to be part of, we look forward to meeting you!

YOUR ROLE:

• Managing the onboarding and implementation of new benefits plans.
• Working with insurance carrier partners to ensure their systems are built with the correct plan specifications.
• Managing the review and delivery of policy contracts.
• Leading ongoing enrollment strategy and logistics for all Union One group plans.
• Coordinating the build and launch of dedicated benefits websites and member portals.
• Running point on creation and delivery of enrollment and education materials.
• Developing and executing effective enrollment communication strategies.
• Overseeing census collection, eligibility setup, and data validation.
• Ensuring smooth post-enrollment processes, including reporting, updates, and client support.
• Managing multiple projects simultaneously and ensuring timely communication across teams (technology, sales, operations, etc.).
• Building and refining standard operating procedures (SOPs) to improve implementation workflows.
• Building and managing strong insurance carrier relationships.