Benefits Specialist

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The Role

The Benefits Specialist will support benefits and the leave of absence functions for Green Thumb Industries’ 5,000+ employees. You will be a key member of the Total Rewards and overall People Team. Your main responsibility will be the administration of our benefits programs and 401(k) plan. Additionally, you will provide support for administration of all leave programs, ADA accommodation requests and all related compliance. You are highly organized, responsive and committed to meeting deliverable deadlines with exceptional attention to detail and a high level of accuracy. You excel in a fast-paced environment and are excited to learn new systems, improve upon current practices, support ongoing communication and education initiatives and interact directly with employees at all levels.

This is a remote position, but Chicagoland area candidates are preferred. In office expectations are on an as needed basis to our Chicago (River North) office.

Responsibilities

• Benefits Administration• Support the administration of all company benefit programs, in partnership with external vendors as applicable.

• Administer benefits onboarding and offboarding for Green Thumb teammates, including COBRA compliance.

• Process employee status changes (e.g., part-time to full-time and vice versa) and ensure accurate benefits updates.

• Provide guidance and counsel to employees and managers regarding benefit programs, eligibility, and issue resolution. Comfortable delivering live presentations.

• Compliance & Regulatory Oversight• Partner with the ACA vendor to monitor and maintain ACA compliance, including affordability calculations, minimum value determinations, and reporting requirements.

• Ensure timely distribution of all required annual compliance communications.

• Auditing & Reporting• Conduct regular audits of benefit records to ensure data accuracy and consistency across internal systems and external vendors.

• Perform monthly enrollment audits and reconcile benefits billing.

• Open Enrollment & Education

• Support the annual open enrollment process, including communication strategy, system updates, and employee education.

• Collaborate to develop and deliver benefits education programs and materials.

• Leave Administration

• Serve as liaison between employees, managers, HR, and the third-party leave administrator to support the full leave lifecycle, from initial request through return to work.

• Facilitate ADA interactive process discussions, review accommodation recommendations, and consult with management and Employee Relations on determinations.

• Advise stakeholders on the interaction of federal, state, and local leave laws (including FMLA and ADA) with company policies, PTO, workers’ compensation, and disability benefits.

• Monitor leave activity, including intermittent leave usage, benefits eligibility, and premium reconciliation, ensuring accuracy and compliance.

• Maintain accurate, confidential leave and accommodation records in accordance with legal requirements and best practices.

• Respond to leave and disability-related inquiries and ensure timely processing of related pay and benefits adjustments, including payroll updates.

• Support administration of company time-off programs and recommend policy updates to maintain compliance and operational efficiency.

Qualifications

• Bachelor’s degree in Human Resources, Business Administration, or related field preferred, or equivalent combination of education and experience.
• 2+ years of experience in benefits administration.
• Working knowledge of federal and state employment and benefits laws including COBRA, ERISA FMLA, ADA, ACA, and related regulations.
• Experience working with third-party administrators, benefits vendors, and HRIS systems
• Strong attention to detail with the ability to manage sensitive and confidential information.
• Effective communication and problem-solving skills, with the ability to support employees and managers in a service-oriented environment.

Additional Requirements

• Must pass any and all required background checks
• Must be and remain compliant with all legal or company regulations for working in the industry
• Must be a minimum of 21 years of age

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The pay range is competitive and based on experience, qualifications, and/or location of the role. Positions may be eligible for a discretionary annual incentive program driven by organization and individual performance.

Green Thumb Pay Range

$70,000—$85,000 USD