Christopher Stevenson

Benefits Manager | Connecting Employees to Total Rewards | HR Data Analysis & Operations | Startups, Technology, Strategic Planning, Project Management

Chicago, Illinois, United States

About

As an experienced benefits manager and administrator, I excel at connecting employees to existing benefits and working with vendors to enhance my company’s Total Rewards offerings. ► Areas of My Expertise - 6 years of benefits administration and management across all 50 states. - Collaboration across all company departments. - Experience working with all levels of employees, from hourly employees to C-suite executives. - HRIS management and deployment, including ADP Workforce Now, Rippling, Greenlink, and UKG Pro. ► Problems I Solve - Open Enrollment planning, management, and communication. - Billing and coverage disputes at both the employee and corporate level. - Data Analysis and trend reporting, to get ahead of potential problems. - Data feed issues between HRIS, benefits providers, and payroll processing. ► Wide Variety of Industries & Startups - I have worked in multiple fast-paced industries including micromobility, cannabis, app development, retail, and payroll. - I prefer a startup environment, with the ability to move fast and make bold moves, while keeping in mind that you can’t move so fast that you break employees’ benefits.

Experience

  • Benefits Specialist at Columbia College Chicago
    Feb 2026 - May 2026 · 4 mos

    ● Administers group benefits programs, including medical, dental, vision, life, disability and retirement plans for 500 union, non-union, and faculty employees ● Manages enrollments, COBRA administration, claims support and employee benefit inquiries ● Partners with external vendors and brokers to ensure service excellence and cost efficiency ● Supports audits, compliance testing and benefits-related reporting ● Oversees FMLA administration and employee leave management ● Maintains accurate and up-to-date benefits data within HRIS platforms ● Assists with benefits communications and leads open enrollment initiatives

  • Benefits Analyst at Ascend Wellness Holdings (CSE: AAWH.U / OTCQX:AAWH)
    Dec 2024 - Dec 2025 · 1 yr 1 mo

  • Employee Experience Manager at Veo
    Sep 2021 - Feb 2024 · 2 yrs 6 mos

  • Payroll & Benefits Coordinator at Pangea Properties
    Sep 2020 - Sep 2021 · 1 yr 1 mo

    ● Managed payroll for 350 employees nationwide using UKG Pro system ● Led the transition between health insurance providers during open enrollment with educational sessions ● Handled workers' compensation policies for an active workforce in three states ● Oversaw leave of absence management, benefits inquiries, and end-to-end payroll processes

  • Senior Payroll and Benefits Specialist at Rightpoint
    Apr 2019 - Jun 2020 · 1 yr 3 mos

    ● Processes all elements of payroll for 450 person cross-country workforce through ADP Workforce Now ● Responsible for initial setup, team member questions, ensuring paychecks are received, and all payroll-related tax filings and issues ● Administers benefits for the same workforce, through two different health insurance providers and several other benefits partners. Ensures that benefit issues are quickly resolved and answers team member inquiries ● Runs annual open enrollment sessions, including building SharePoint information sites, sending out reminders, updating information, and assisting team members in finding the right plans for them ● Created and runs company-wide wellness program, including in-office yoga and massages, financial seminars, flu shot clinics, and information posters for physical, mental, and financial wellness