Gallagher Finance/FinTech

Medicare Team Sales Manager

Chicago, IL In person Full-time

Introduction

At Gallagher Benefit Services, you’re a trusted partner to organizations navigating some of their most important people decisions. We help clients build better workplaces, where people feel supported, empowered, and inspired to thrive. Whether it’s shaping benefit strategies, designing wellbeing programs, or advising on workforce challenges, the work you do here creates meaningful change for businesses and the people who power them.

We’re a community of bold explorers, trusted experts, and compassionate partners; working side by side to solve problems, and shape the future of work. Here, curiosity is encouraged, collaboration is second nature, and your ideas have room to grow. If you’re looking for a place where your contribution matters and where you can help build a better world of work; think of Gallagher.

Overview

Your Way Insurance is a people-first organization built on compassion, integrity, and service. Our greatest strength lies in our talented and driven team, dedicated to helping seniors find Medicare plans that truly fit their needs, the right way. Through our one-stop shopping experience, we make it easy to compare top national health insurance carriers and choose coverage with confidence.

Now part of Gallagher, a global leader in insurance, risk management, and consulting, you’ll join a network of professionals committed to empowering individuals, businesses, and communities to thrive. Whether you're supporting clients directly or contributing behind the scenes, you'll be part of a culture defined Your Way: shared values, excellence, and a passion for doing what's right.

We are hiring now for January 2027! An application will only take three minutes.

How you'll make an impact

In this role, you'll lead a team of Medicare Consultants, helping them deliver outstanding experience for every customer while achieving sales and performance goals. You'll provide day-to-day coaching, share feedback that helps advisors grow, and create an environment where people can do their best work. You'll use performance data to identify opportunities, remove obstacles, and drive consistent results across the team.

You'll also work closely with partners across training and operations to improve processes and support business growth. As Medicare regulations and products evolve, you'll help ensure your team stays informed, compliant, and prepared to guide customers with confidence.

Key responsibilities include

  • Lead, coach, and develop a team of approximately 10-15 Medicare Sales Consultants.
  • Monitor sales, productivity, quality, and customer experience metrics.
  • Conduct regular coaching sessions, performance reviews, and development planning.
  • Support new hire onboarding and ongoing training initiatives.
  • Ensure adherence to Medicare regulations, carrier requirements, and company policies.

About You

  • High school diploma or equivalent required; bachelor's degree preferred.
  • Active Health Insurance License in your resident state prior to start date, maintained in good standing.
  • AHIP certification preferred.
  • Medicare Line of Authority (LOA) required for residents of North Carolina.
  • Experience leading and developing a team of approximately 10 sales professionals in a Medicare, insurance, contact center, or related sales environment.
  • Working knowledge of Medicare products, enrollment guidelines, compliance requirements, and sales processes.
  • Ability to review performance metrics, identify trends, and take action to improve results.
  • Ability to provide coaching, feedback, and performance management to support employee development.
  • Ability to communicate policy, process changes, and business updates clearly with team members and business partners.
  • Dedicated private workspace free from distractions and the ability to maintain a reliable, hardwired internet connection for business use.

Compensation and benefits

At Gallagher, we believe supporting our colleagues goes far beyond the role itself. For more information, visit our Benefits page.

Competitive compensation

Comprehensive benefits programs designed to support your well-being

Career development opportunities and ongoing learning

A collaborative, people-first culture with accessible leadership

The opportunity to do meaningful work with global reach and local impact

At Gallagher, we are dedicated to building an inclusive and authentic workplace. If your past experience doesn’t align perfectly, we encourage you to join our Talent Community to stay connected to additional career opportunities. At times, we will consider transferable skills from previous roles.

Gallagher is an affirmative action/equal opportunity employer (Minorities/Females/Veterans/Disabled)

Job description provided by Gallagher.
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