Senior Manager, Leaves and Accommodations

Green Thumb • Chicago, IL

2d • Remote

About The Position

The Senior Manager, Leaves & Accommodations oversees the leave of absence and accommodation Center of Excellence (COE) and serves as the organization’s primary subject matter expert on leave management, reasonable accommodations, the interactive process, and state and local leave and disability laws. The role leads the administration and oversight of leave programs, including FMLA, ADA, PWFA, state and local leave laws, disability benefits, and company-issued leave programs. The Senior Manager builds and develops team structures and processes, drives operational excellence, mitigates legal and compliance risk, and enhances leave and accommodation processes while responding to complex and evolving regulatory requirements. This is primarily a remote position; Chicagoland candidates are preferred.

The role provides strategic leadership for scalable policies and operational frameworks, develops a customer service-oriented team, establishes service expectations and goals, and advances continuous process improvement. It advises senior leaders on complex and confidential employee matters and partners with Benefits, Payroll, HR, Employee Relations, Legal, and Risk. The Senior Manager also oversees compliance, employee education, reporting and analysis, vendor relationships, administration systems, and the full lifecycle of leave cases from intake through return to work.

The position requires at least seven years of related experience and a bachelor’s degree in human resources or a related field with an emphasis in business or finance, or equivalent professional/analytical experience, education, and training. The posted pay range is $120,000–$150,000 USD. Positions may be eligible for a discretionary annual incentive program based on organizational 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, education, and training.
• Demonstrated success and experience leading a center of excellence or leave and accommodation practitioners.
• Extensive knowledge of leave requirements and legal protections under federal, state, and local laws.
• Knowledge of ERISA and employee benefit programs, including flexible benefit programs, financial analysis, and budgeting.
• Ability to analyze complex problems, identify sources of risk, and develop strategic solutions; track record of resolving issues in a timely manner.
• Strong organizational skills, including prioritizing tasks, managing multiple projects, and meeting deadlines.
• Effective leadership and management skills, including the ability to 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 decisions and problem-solving.
• Ability to adapt priorities and strategies in a dynamic work environment.
• Excellent written and verbal communication skills and ability to collaborate effectively with stakeholders.
• Proficiency with Microsoft Office products, advanced Excel skills, and ability to perform mathematical calculations involving rates, premiums, and adjustments.
• Must pass 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.
• Chicagoland candidates are preferred.

Responsibilities

• Own scalable policies and operational frameworks for centralized 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.
• Develop and deliver educational resources about leave and accommodation protocols for employees, HR Partners, and management.
• Use data and reporting to monitor trends, identify risks, and recommend improvements to programs, processes, and employee experience.
• Maintain knowledge of applicable leave and accommodation laws and ensure compliance with them.
• Monitor legislative developments and changes to leave laws and regulations.
• Advise HR Partners, managers, and employees on interactions between leave laws, 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 accurate and complete records of leave and accommodation requests are maintained in accordance with legal requirements and documentation best practices.
• Maintain procedures that support accurate and efficient employee payments, disability claims, benefit premium reconciliations and repayments, and benefits eligibility.
• Develop procedures to monitor the accuracy, timeliness, and compliance of intermittent leave usage.
• Develop and maintain reports and metrics on leaves and accommodations, and deliver actionable analysis to managers and senior leadership.
• Serve as the primary contact for third-party vendors and oversee vendor performance and service delivery.
• Own and optimize leave and accommodation systems and processes, partnering with HRIS and vendors to improve functionality, reporting, and efficiency.
• Manage the full lifecycle of leave cases, including intake, eligibility, notification, documentation, tracking, and return to work.

Benefits

• Positions may be eligible for a discretionary annual incentive program driven by organization and individual performance.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior