HR & Benefits Manager at Flex HR -… · Chicago

Job Title: HR & Benefits Manager

Reports To: Vice President of Human Resources

Location: Remote - out of Chicago, IL

FLSA: Exempt

About Flex HR: Flex HR is a fast-growing HR outsourcing company with offices in Atlanta and Chicago. We work with companies in a variety of industries to help them manage their human resources and payroll. We are a team of professionals who consistently provide our clients with white-glove customer service. We are looking for a positive, self-motivated, dedicated, skilled, customer-focused, and detail-oriented person to join our team and organization.

Job Summary: We are seeking a dedicated and experienced HR & Benefits Manager to join our team. The HR & Benefits Manager provides daily customer service and HR operational support to our clients and leads their benefits programs, including annual open enrollment. This position will be a trusted advisor to client leadership and employees, working closely with insurance brokers, vendors, and our internal HR and payroll teams to ensure programs meet employee needs, are competitive, comply with legal requirements, and are cost effective. The HR & Benefits Manager will also support personnel actions such as new hire offer letters, onboarding, terminations, employee relations, conflict resolution, leave of absence management, unemployment/workers' compensation claims, multi-state compliance, and policy development.

Job Responsibilities:

• Serve as a trusted advisor and point of contact for clients and their employees
• Manage onboarding from offer letter through HRIS/payroll setup
• Coach managers on performance improvement plans (PIPs) and support terminations, including state-specific forms and serving as a witness on termination calls
• Handle employee relations, conflict resolution, leaves of absence, and unemployment and workers' compensation claims
• Oversee benefits for outsourced clients, recommending plan improvements based on market trends and employee feedback
• Lead annual open enrollment, from sending the census to brokers through getting elections processed by the first effective payroll date
• Work with brokers and vendors on benefit communications and employee education
• Assist employees with benefit enrollments, HSA/FSA changes, and 401(k) rollover, loan, and distribution paperwork
• Track benefit deductions in payroll platforms and complete monthly invoice reconciliations
• Complete periodic audits and maintain accurate client records, the core company data sheet (CCDS), and a six-month open enrollment schedule
• Lead quarterly client reviews and virtual office hours, and support employee engagement such as birthday and anniversary updates
• Train HR team members on benefits and compliance, and document benefits processes
• Ensure multi-state compliance and develop policies and procedures that reflect best practices
• Work in multiple payroll and HRIS platforms
• Build strong relationships with clients, coworkers, and management, and complete special projects as assigned

General Job Requirements:

• Be part of an organization that is team-based, positive and helpful.
• Always make ethical decisions.
• Continue to learn in your field and make improvements with your HR and benefits knowledge.
• Help to think critically about how to solve problems and how to work smarter, not harder.

Job Requirements:

• 3-5 years of experience as an HR Manager or in a similar role supporting multiple duties, preferably in an outsourced or consulting capacity
• Experience in benefits management, with a focus on annual open enrollment and benefit plan design
• Strong knowledge of HR best practices, labor laws, multi-state compliance, and regulations
• Experience working with insurance brokers and vendors, with strong negotiation skills
• Proficiency in HRIS, payroll, and benefits administration software; familiarity with ADP, Paylocity, Paychex, Paycom, Paycor, UKG, Gusto, or Netchex is highly desirable
• Strong skills in PowerPoint, Excel, and Word
• Excellent communication, interpersonal, analytical, and leadership skills to interact effectively with employees at all levels of the organization
• Strong math skills for calculating benefit costs
• Ability to handle sensitive information confidentially and professionally
• Strong attention to detail, exceptional problem-solving and critical thinking skills, and the ability to manage multiple priorities in a fast-paced environment
• Strong discipline to work independently, prioritize and manage workload, and balance time between calls and processing requests for multiple clients
• Must use a cell phone to monitor client needs, including accessing Flex HR email
• A minimum of an associate's degree in a related field or equivalent work experience (a plus)
• HubSpot experience is a plus

Featured Benefits:

• Comprehensive Medical/Dental/Vision benefits with a significant portion of the premium covered by the company
• HSA, FSA and Dependent Care spending accounts
• Company-paid Employee Assistance Program (EAP) and short-term disability
• 401(k) plan with a 4% company match
• Flexible paid time off starting at 3 weeks per year, increases with length of service
• 12 paid holidays annually
• Educational assistance
• Company wellness program through Wellsteps

Featured Perks:

• $250 employee referral bonus
• Monthly tech reimbursement
• Birthday day off
• Continuous training and development
• Virtual Flex Fun Club
• Employee discount savings program
• Great remote working environment (energetic, friendly, fun, and collaborative)
• Access to a financial advisor for financial planning and consulting

Starting base salary at $70,000 per year.

Work Environment: The work environment characteristics described here are representative of those an employee encounters while performing essential job functions. Reasonable accommodation may be made to enable individuals with disabilities to perform essential job functions. In the general office environment, some stress may occur in meeting project deadlines. In this job, you will use office equipment and the computer for approximately 90% of the workday.

Flex HR uses AI for document preparation and meeting transcription only — never to screen or evaluate candidates. All hiring decisions are made by a human recruiter. Roles may be posted on platforms like Indeed or LinkedIn, which are independent companies that may use AI in their own technology.