Director of Compliance and Marketing

Gallagher•Chicago, IL

12h

About The Position

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. Your Way Insurance is seeking a dynamic Director of Compliance & Marketing to join its growing Legal & Compliance department. This role will serve as a strategic leader, thinker, and business partner to one of the largest and fastest-growing Medicare brokerages in the nation. The position reports directly to the Head of Legal & Compliance.

Requirements

JD, MHA, or MBA strongly preferred; Bachelor’s degree required.
8–10+ years in Medicare/health plan compliance with 5+ in leadership
Developed sense of business judgment obtained via a minimum of 8 to 10 years of experience working with a compliance program within a highly regulated industry.
Strong writing and communication skills, such as executive presentation and reporting.
Comfort in policy drafting and creating processes to drive results at scale.

Nice To Haves

CMS regulations (42 CFR Parts 422 and 423), Medicare Managed Care Manual, and Prescription Drug Benefit Manual
CMS marketing guidelines
Experience with carrier or regulatory audits
Experience with HPMS, FDR oversight, and CAP management
HIPAA Privacy and Security regulations
Data analytics, such as PowerBI, Excel, and Artificial Intelligence Platforms

Responsibilities

Oversee all aspects of Your Way Insurance’s Compliance program.
Act as the primary liaison with TPMOs, carriers, and regulators during audits, inquiries, and corrective action plans (CAPs).
Assist in compliance training, monitoring, and auditing to ensure adherence to applicable policies, procedures, and regulatory requirements.
Monitor evolving statutory, regulatory, and carrier requirements, updating compliance programming to align with new standards.
Review scripts, training materials, and marketing content prior to each enrollment period to ensure compliance.
Develop and maintain policies, procedures, the annual compliance work plan, and risk assessments.
Support internal investigations, reports, or complaints related to suspected FWA violations, including CTMs, DOI investigations, and government inquiries.
Deliver compliance training, including general compliance and FWA training sessions.
Coordinate with TPMO’s and carriers regarding compliance metrics and marketing requirements
Maintain compliance metrics and ensure timely, accurate reporting.
Collaborate with Your Way Insurance leadership to strategize on risk mitigation and monitor compliance metrics effectively.

Benefits

Medical/dental/vision plans, which start from day one!
Life and accident insurance
401(K) and Roth options
Tax-advantaged accounts (HSA, FSA)
Educational expense reimbursement
Paid parental leave
Digital mental health services (Talkspace)
Flexible work hours (availability varies by office and job function)
Training programs
Gallagher Thrive program – elevating your health through challenges, workshops and digital fitness programs for your overall wellbeing
Charitable matching gift program