Demo

Customer Service Manager

Flexible Benefit Service LLC (Flex)
Chicago, IL Full Time
POSTED ON 4/28/2026
AVAILABLE BEFORE 5/27/2026

Ready to Lead a High-Impact Service Operation — Not Just Manage One?

Exceptional service doesn’t happen by accident. It takes strong leadership, operational discipline, and a manager who knows how to turn people, process, and performance into a competitive advantage.

Flexible Benefit Service LLC (Flex) is looking for a Customer Service Manager to lead a critical service organization supporting CDHP, COBRA, FSA, and HSA solutions—and help shape the next phase of our operational growth.

This is more than a traditional customer service leadership role. It’s an opportunity to influence strategy, elevate performance, develop talent, and make a visible impact across the business.

If you are a hands-on leader who can coach teams, improve service operations, solve problems at the root cause, and raise the bar on the customer experience—we want to talk.

Why This Role Stands Out

High Visibility. High Impact. Real Influence.

In this role, you will:

  • Lead and develop a team of service professionals supporting a growing client base
  • Own service performance across calls, email, and service workflows
  • Drive KPI-based accountability, operational discipline, and continuous improvement
  • Partner cross-functionally with Sales, Account Management, IT, Compliance, and Operations leadership
  • Help strengthen the service model that supports customer retention and business growth
  • Play a meaningful role in shaping how service excellence is delivered at Flex

What You’ll Bring

We’re looking for a leader who combines operational rigor with people leadership.

You may be a strong fit if you have:

  • 3–5 years leading customer service or contact center operations
  • Experience managing performance through service metrics, SLAs, QA, and KPIs
  • A track record of coaching and developing high-performing teams
  • Experience improving workflows, solving operational challenges, and driving efficiencies
  • Benefits administration, healthcare, TPA, CDHP, COBRA, FSA, or HSA experience (strongly preferred)
  • Experience with CRM or service technologies such as Dynamics or similar platforms

What Success Looks Like

You know how to move the metrics that matter:

  • Strong service performance and response times
  • High-quality customer outcomes
  • Engaged, accountable teams
  • Continuous improvement that drives measurable results
  • Operational leadership that scales with growth

Why Flex?

At Flex, you won’t be stepping into a rigid environment where you simply maintain the status quo.

You’ll have the opportunity to:

  • Make a visible impact
  • Help shape process and performance improvements
  • Work alongside collaborative, experienced leaders
  • Grow your leadership scope
  • Join a company where your ideas and results matter

If You’re Looking For…

✔ A leadership role with influence

✔ A chance to improve and build, not just manage

✔ A growth-oriented organization where you can make your mark

✔ A team and culture that values accountability, service, and collaboration

This may be your next move.


Apply Today

If you’re ready to lead, improve, and elevate service performance in a meaningful way, we’d like to hear from you.

Work Location: Hybrid remote in Chicago, IL 60631

Salary.com Estimation for Customer Service Manager in Chicago, IL
$108,498 to $137,434
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