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Manager, Benefits

Green Thumb Industries
life insurance, sick time, 401(k)
United States, Illinois, Chicago
325 West Huron Street (Show on map)
Aug 20, 2025
The Role

Green Thumb is seeking an experienced Benefits Manager to join our Total Rewards team. This role will work closely with the Director of Benefits on a wide range of strategic initiatives and projects while overseeing and providing direct supervision and guidance to a Benefits Specialist and managing the day-to-day administration of our comprehensive employee benefits programs with a high level of accuracy. The position ensures full compliance with all state and federal regulations including ACA, ERISA, COBRA, HIPAA, ADA and FMLA and serves as a subject matter expert within the benefits function. The successful candidate will serve as the primary point of contact for all benefits-related inquiries, and play a critical role in supporting our employees in a demanding, fast-paced environment.


Responsibilities

Management & Strategic Collaboration

* Partner closely with the Director of Benefits on strategic initiatives, program development, and organizational benefits objectives

* Provide direct supervision, coaching, and professional development to Benefits Specialist. Conduct performance reviews, set goals, and support career development.

* Lead cross-functional project teams and collaborate on benefits-related projects spanning multiple departments

* Drive process improvements and operational excellence within the benefits function

* Serve as escalation point for complex benefits issues and vendor management relationships

Benefits Administration

* Partner with Director of Benefits to design, implement, and manage comprehensive employee benefits programs including health, dental, vision, life insurance, disability, and retirement plans

* Partner with benefits vendors and broker to negotiate contracts, evaluate plan options, and ensure competitive offerings

* Oversee annual open enrollment process, including communication strategies, system updates, and employee education

* Conduct regular benefits plan analysis and cost management to optimize value for both employees and the organization

* Maintain accurate benefits records, monitor/maintain/update vendor file feeds and ensure seamless integration with HRIS system

Compliance Management

* Ensure full compliance with federal benefits regulations including ACA, ERISA, COBRA, HIPAA, ADA, FMLA and all applicable state and local laws * Stay current with evolving cannabis industry regulations and their impact on employee benefits

* Prepare and file required regulatory reports and documentation

* Monitor all federal, state and local regulatory benefits/paid leave/sick leave updates and ensure timely, appropriate action is taken to ensure compliance * Conduct regular compliance audits and implement corrective measures as needed

* Collaborate with legal counsel on benefits-related compliance matters

ACA Compliance

* Partner with ACA vendor to monitor and maintain ACA compliance including affordability calculations, minimum value determinations, and reporting requirements

* Prepare and file Forms 1094-C and 1095-C annually

* Track employee eligibility and ensure proper enrollment processes

* Manage ACA penalty risk and optimization strategies

ERISA Administration

* Oversee ERISA plan administration including plan documents, summary plan descriptions, annual reporting and all related required participant notifications

* Ensure proper fiduciary responsibilities are met for retirement and welfare benefit plans

* Coordinate with third-party administrators to ensure timely Form 5500 filing

* Monitor 401(k) deferral changes to ensure accurate employee contributions

* Oversee all non-discrimination testing and take required corrective action Employee Communication & Support

* Serve as primary benefits subject matter expert for employees and management

* Develop and deliver benefits education programs and materials

* Resolve complex benefits issues and escalations

* Support total rewards communication strategies

Leave of Absence Support

Support Leave of Absence Manager as needed to:

* Administer all leave programs including FMLA, ADA, state family/medical leave and workers' compensation

* Partner with leave team, HR partners, employees and managers to facilitate smooth leave transitions and return-to-work processes

* Ensure proper documentation, certification, and compliance with all applicable leave laws

* Maintain confidential leave records and coordinate benefits continuation/premiums owed


Qualifications

Required Qualifications

* Bachelor's degree in Human Resources, Business Administration, or related field; or equivalent combination of education, training, and/or experience preferred

* 5+ years of large-employer (1000+ variable hour employees), progressive benefits administration experience

* 2+ years of supervisory or management experience

* Strong knowledge of state and federal benefits regulations (ACA, ERISA, COBRA, FMLA, ADA, HIPAA)

* Experience with benefits compliance testing, auditing and reporting

* Proficiency with HRIS systems, benefits administration platforms and vendor file management

* Experience managing vendor relationships

* Knowledge of state-specific benefits and leave laws

* Advanced data aptitude and attention to detail with advanced Excel capabilities

* Excellent analytical and problem-solving skills

* Strong attention to detail and ability to manage multiple priorities

* Exceptional written and verbal communication skills

* Demonstrated ability to coach and develop team members

Preferred Qualifications

* Certified Employee Benefits Specialist (CEBS) or similar professional certification
* Experience in cannabis industry or other highly regulated industry
* Project management experience


Additional Requirements

  • Must passany and allrequired 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

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
$100,000 $115,000 USD
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