HR Generalist Jobs in Chicago, IL

Canopy Service Partners is a collaborative, growth-oriented organization dedicated to supporting local partner businesses across the tree care industry. We are building a high-performing Employee Services function that combines reliable HR operations with responsive, practical support for employees and leaders across a growing, multi-state organization.

As the HR Generalist, you will own essential processes that affect every employee, with primary responsibility for weekly payroll, day-to-day benefits administration, and core HR operations. You will process 10 to 13 payrolls each week, support payroll and employment compliance across multiple states, administer benefits and 401(k) processes, manage shared employee-service inboxes, and coordinate onboarding and offboarding. You will also serve as a first point of contact for routine HR questions and work closely with our HR Business Partners to ensure employees and managers receive timely, accurate support.

This is an excellent opportunity for an early-career HR professional who has strong payroll fundamentals, enjoys solving problems, and wants to grow. Canopy is implementing Paycom, giving this person meaningful exposure to an enterprise HRIS transition and the opportunity to help improve processes as the company scales. Depending on performance, interests, and business needs, potential career paths may include senior HR operations, payroll and benefits leadership, or an HR Business Partner role.

This role reports to the HR Operations Leader and may be performed remotely from a state where Canopy currently operates. Candidates located in Chicago or Charlotte are strongly preferred. If based outside Chicago, occasional travel for quarterly team meetings is expected. Bilingual English/Spanish capability is strongly preferred because this role directly supports a large Spanish-speaking employee population.

Responsibilities

Payroll and Compliance

• Process 10 to 13 end-to-end weekly payrolls accurately and on time, including employee changes, hourly pay, overtime, bonuses, commissions, deductions, exceptions, and manual checks.
• Review payroll inputs, reconcile payroll registers, audit employee and payroll data, investigate discrepancies, and drive issues through resolution.
• Maintain payroll calendars, controls, documentation, and approval processes across multiple legal entities and states.
• Support compliance with federal, state, and local wage-and-hour and payroll requirements, including requirements in California, Massachusetts, Minnesota, Illinois, and other states where Canopy operates.
• Manage payroll tax registrations, agency notices, garnishments, wage notices, required state and local reporting, and related employee communications.
• Coordinate year-end payroll activities, including employee data audits, W-2 processing, reconciliations, corrections, and employee support.
• Support workers' compensation, payroll, retirement plan, and other internal or external audits by preparing accurate records and resolving open items.

Benefits and Retirement Administration

• Own day-to-day administration of medical, dental, vision, life, disability, and voluntary benefit programs, including enrollments, qualifying life events, status changes, terminations, employee questions, and issue resolution.
• Reconcile benefit enrollments, payroll deductions, carrier records, and invoices; investigate and resolve discrepancies promptly.
• Administer day-to-day 401(k) processes, including contribution changes, payroll funding coordination, employee questions, compliance support, and vendor follow-up.
• Support annual open enrollment and benefits onboarding for newly acquired partner companies, including employee communications, enrollment support, data validation, and follow-through.
• Coordinate employee leaves with Lincoln, Canopy's leave administrator, and ensure related payroll, benefits, HRIS, and employee communications are accurate and timely.
• Partner with the HR Operations Leader on benefits renewals, plan changes, audits, reporting, and other program initiatives.

HR Operations and Employee Support

• Manage shared Employee Services inboxes by triaging requests, providing accurate and responsive support, tracking issues to resolution, and escalating complex or sensitive matters appropriately.
• Coordinate employee onboarding and offboarding, including required documentation, HRIS updates, benefits and payroll setup, I-9 completion, and communication with employees and internal partners.
• Maintain accurate, complete, and confidential employee records across multiple entities and systems.
• Serve as a first point of contact for routine questions about payroll, benefits, policies, employment records, and other HR matters.
• Work closely with HR Business Partners to provide first-line employee and manager support and coordinate follow-up on matters requiring HRBP involvement.
• Support the transition from Inova to Paycom by assisting with data validation, testing, process documentation, employee support, and adoption of new workflows.
• Identify opportunities to simplify work, strengthen controls, improve the employee experience, and create scalable HR processes for a growing organization.
• Contribute to cross-functional projects and company priorities outside of regular day-to-day responsibilities.

Qualifications

• 1 to 4 years of experience in human resources, payroll, benefits, HR operations, or a related field.
• Hands-on payroll experience and a strong understanding of payroll fundamentals are required; experience independently processing payroll from start to finish is strongly preferred.
• Experience supporting multi-state payroll, wage-and-hour compliance, benefits administration, or employee lifecycle processes is preferred.
• Experience using a payroll or HRIS platform; Paycom experience is a plus.
• Bilingual English/Spanish capability is strongly preferred, including the ability to discuss payroll, benefits, policies, and other HR matters clearly with employees.
• Strong attention to detail and a commitment to accuracy, confidentiality, and timely follow-through.
• Responsive, service-oriented communication style and the ability to build trust with employees, local leaders, vendors, and HR partners.
• Sound judgment, curiosity, and persistence when investigating issues and resolving problems.
• Resilient, flexible, and adaptable, with the ability to manage competing priorities in a fast-changing, growth-oriented environment.
• Comfort learning new systems, improving processes, and taking on increasing responsibility over time.
• Bachelor's degree, payroll certification, or HR certification is a plus but not required.

Compensation

The base salary range for this position is $65,000 to $75,000. This role is also eligible for an annual bonus opportunity of up to 20% of base salary, based on company performance and individual performance against established goals. Final compensation will be determined based on relevant experience, skills, location, and internal equity.

Benefits

• Employees who work 30 or more hours per week are considered full-time and become eligible for benefits after 30 days of employment.
• Paid time off and paid holidays
• Employer-paid short-term disability insurance
• Employer-paid long-term disability insurance
• Employer-paid basic life and AD&D insurance
• 401(k) retirement plan with up to a 4% company match
• Multiple Cigna medical plan options, including a broad-access OAP plan, an in-network OAP plan, and a high-deductible health plan with HSA eligibility
• Multiple Cigna dental plan options and comprehensive Cigna vision coverage
• $250 employer HSA contribution for employees enrolled in a high-deductible health plan, or access to health care and dependent care flexible spending accounts
• Pre-tax commuter benefits for parking, transit, and vanpool expenses
• Optional legal assistance, critical illness, accident, and hospital indemnity coverage

About Canopy Service Partners

Canopy Service Partners is a national platform of locally led tree care companies. We partner with strong businesses and preserve the brands, relationships, and local expertise that made them successful while providing resources that help them grow. Our Partner Services team supports approximately 20 operating businesses across a multi-state footprint, with a focus on sustainable growth, operational excellence, and an exceptional employee experience.

Equal Employment Opportunity

Canopy Service Partners is an equal opportunity employer. We make employment decisions based on qualifications, merit, and business needs and prohibit discrimination or harassment based on any characteristic protected by applicable federal, state, or local law. This commitment applies to all employment practices, including recruiting, hiring, compensation, promotion, training, leaves of absence, and termination.

Offered compensation: $65,000/yr - $75,000/yr

Experience and License Requirements

• Benefits Administration (optional)
• Payroll Administration