Senior Manager, Leaves and Accommodations

Green Thumb•Chicago, IL

2d•$120,000 - $150,000•Remote

About The Position

The Senior Manager, Leaves and Accommodations oversees the leave of absence and accommodations Center of Excellence (COE) and serves as the organization’s primary subject matter expert on leave management, reasonable accommodations and the interactive process, and state and local leave and disability laws. This leadership role oversees leave programs, including FMLA, ADA, PWFA, state and local leave laws, disability benefits, and company-issued leave programs. The role builds and develops the team structure and processes, drives operational excellence, mitigates legal and compliance risk, and improves leave and accommodation processes while navigating complex and evolving regulatory requirements. The position leads the COE’s strategy, team development, service standards, and continuous improvement. It provides guidance to senior leaders and partners across Benefits, Payroll, HR, Employee Relations, Legal, and Risk. It also ensures compliance, accurate records, effective administration of leave cases and benefits, and the use of reporting and analysis to improve programs and employee experience. This is primarily a remote position; Chicagoland candidates are preferred. The pay range is $120,000–$150,000 USD, based on experience, qualifications, and/or location. Positions may be eligible for a discretionary annual incentive program driven by organization and individual performance.

Requirements

At least 7 years of related experience.
Bachelor’s degree in human resources or a related field with an emphasis in business or finance, or equivalent professional/analytical experience or a combination of education, experience, and training.
Demonstrated success and experience leading a center of excellence or leave and accommodations practitioners.
Extensive knowledge of leave requirements and legal protections under federal, state, and local laws.
Well versed in ERISA and employee benefit programs, including flexible benefit programs, financial analysis, and budgeting.
Proficiency in analyzing complex problems, identifying risks, and developing strategic solutions, with a record of timely issue resolution.
Strong organizational skills, including prioritizing tasks, managing multiple projects, and consistently meeting deadlines.
Effective leadership and management skills, including the ability to inspire and motivate a high-performance team.
Ability to maintain confidentiality and handle sensitive information with discretion and professionalism.
Ability to critically analyze information, data, and situations to identify patterns and support informed decision-making and problem-solving.
Flexibility and adaptability in dynamic work environments and changing priorities.
Excellent written and verbal communication skills and the ability to explain complex ideas clearly and collaborate with stakeholders.
Proficiency with Microsoft Office products, advanced Excel experience, and ability to perform mathematical calculations involving rates, premiums, and adjustments.
Must pass all required background checks.
Must remain compliant with legal and company regulations for working in the industry.
Must possess a valid driver’s license.
Must be at least 21 years of age.
Must be approved by the state badging agency to work in the cannabis industry.

Nice To Haves

Experience with AbsenceSoft.
Familiarity with the Workers’ Compensation Act, city regulations, and other applicable state and federal statutes and regulations.
Experience with Kronos or Wurk.

Responsibilities

Own scalable policies and operational frameworks for centralized management of leave and accommodation programs.
Lead and develop a high-performing, customer service-oriented team of leave and accommodation practitioners.
Establish performance expectations, service level agreements, and operational goals for the COE.
Identify opportunities for continuous process improvement and execute program enhancements.
Provide counsel and technical guidance to senior leaders on complex and confidential employee matters.
Partner with senior leaders across Benefits, Payroll, HR, Employee Relations, Legal, and Risk.
Direct development and delivery of educational resources for employees, HR Partners, and management on leave and accommodation protocols.
Use data and reporting to monitor trends, identify risks, and develop recommendations to mitigate risk and improve programs, processes, and employee experience.
Maintain knowledge of and ensure compliance with applicable leave and accommodation laws.
Monitor legislative developments and changes in leave laws and regulations.
Advise HR Partners, managers, and employees on how leave laws interact with paid time off, workers’ compensation, and short- and long-term disability benefits.
Administer assigned company time-off programs in accordance with internal policy and applicable laws.
Ensure complete and accurate maintenance of leave and accommodation records in accordance with legal requirements and documentation best practices.
Lead procedures that ensure accuracy and efficiency for employee payments, short- and long-term disability claims, benefit-premium reconciliation and repayments, and benefits eligibility.
Develop a procedure to monitor the accuracy, timeliness, and compliance of intermittent leave usage.
Develop and maintain reports and metrics for leaves and accommodations, and analyze them for managers and senior leadership.
Serve as primary contact for third-party vendors, overseeing vendor performance and service delivery.
Own and optimize leave and accommodation systems and processes, partnering with HRIS and vendors to improve functionality, reporting, and operational efficiency.
Manage the full lifecycle of leave cases, including intake, eligibility, notification, documentation, tracking, and return to work.