Associate Director of Compliance, Employee Benefits - Insurance Advisory Solutions

The Baldwin Group is an award-winning entrepreneur-led and inspired insurance brokerage firm delivering expertly crafted Commercial Insurance and Risk Management, Private Insurance and Risk Management, Employee Benefits and Benefit Administration, Asset and Income Protection, and Risk Mitigation strategies to clients wherever their passions and businesses take them throughout the U.S. and abroad. The Baldwin Group has award-winning industry expertise, colleagues, competencies, insurers, and most importantly, a highly differentiated culture that our clients consider an invaluable expansion of their business. The Baldwin Group (NASDAQ: BWIN), takes a holistic and tailored approach to insurance and risk management.


The Associate Director, Benefits Compliance serves as a trusted compliance advisor to both clients and internal teams, providing practical guidance on a broad range of employee benefits compliance matters. This role partners closely with Client Experience Teams and clients to identify, assess, and address compliance risks while helping organizations navigate complex federal health and welfare benefit requirements.

The Associate Director monitors legislative and regulatory developments, translates complex requirements into actionable guidance, and contributes to the development of client-facing resources, educational content, and compliance solutions. The role also serves as a key partner to senior members of the Compliance team, supporting strategic initiatives, client consulting projects, thought leadership efforts, and the ongoing development of the firm's compliance capabilities.

Principal Responsibilities:

• Partner with Client Experience Teams to identify, assess, and address employee benefits compliance risks and support clients in developing practical compliance strategies.

• Provide consultative guidance to clients and internal stakeholders on health and welfare compliance matters, including but not limited to ERISA, ACA, COBRA, HIPAA, Section 125, MHPAEA, and other applicable federal requirements.

• Assist in conducting compliance reviews and assessments, and assist in the development of recommendations and corrective action strategies.

• Research, analyze, and interpret legislative, regulatory, and administrative guidance impacting employer-sponsored benefit plans.

• Monitor regulatory developments and emerging compliance trends and communicate relevant developments to clients and internal stakeholders in a timely manner.

• Develop client-facing communications, alerts, presentations, training materials, and other educational resources regarding regulatory developments and compliance best practices.

• Deliver presentations, webinars, and training sessions to clients, prospects, and internal colleagues.

• Collaborate with internal subject matter experts, external legal counsel, compliance vendors, and carrier partners, as appropriate, to support client needs and ensure accurate guidance.

• Serve as a key partner to senior Compliance leaders by supporting complex client engagements, regulatory initiatives, thought leadership efforts, and the ongoing development of the firm's compliance solutions and resources.

• Contribute to the creation, maintenance, and enhancement of compliance tools, templates, assessments, and other resources used by clients and internal teams.

• Support the Compliance team in maintaining consistent, practical, and client-focused guidance across the organization.

• Demonstrate a commitment to continuous learning and professional development while contributing to a collaborative and high-performing team environment.

Education & Experience:

• 3–5 years of direct health and welfare employee benefits compliance experience required.

• Experience providing compliance consulting to employer-sponsored group health plan clients in a brokerage, consulting, legal, carrier, or third-party administrator environment preferred.

• Demonstrated ability to interpret complex regulatory requirements and translate them into practical, business-focused guidance for clients and internal stakeholders.

• Working knowledge of federal employee benefits laws and regulations, including ERISA, ACA, COBRA, HIPAA, Section 125, MHPAEA, and other health and welfare compliance requirements.

• Bachelor’s degree required; Juris Doctor (JD), Master’s degree, or other advanced degree preferred.

• Strong analytical, research, problem-solving, and critical-thinking skills.

• Excellent verbal, written, and presentation skills, with the ability to communicate complex compliance concepts to diverse audiences.

• Ability to manage multiple priorities and deadlines in a fast-paced, client-focused environment.

• Proficiency in Microsoft Office applications and the ability to learn and effectively utilize firm technology platforms and compliance resources.

• Demonstrated commitment to collaboration, professionalism, and delivering exceptional client service.

Some travel may be required.

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The Baldwin Group will not accept unsolicited resumes from any source other than directly from a candidate who applies on our career site. Any unsolicited resumes sent to The Baldwin Group, including unsolicited resumes sent via any source from an Agency, will not be considered and are not subject to any fees for any placement resulting from the receipt of an unsolicited resume.