People Operations Generalist

Application Deadline: 18 September 2026

Department: Organizational Effectiveness & Development

Employment Type: Full Time

Location: Chicago

Compensation: $50,000 - $65,000 / year

Description

As a People Operations Generalist, you will be a key player in managing the day-to-day functions of our People Operations department. You'll ensure a smooth and positive employee lifecycle from hire to exit. This role requires exceptional organizational skills, a keen eye for detail, and a proactive approach to problem-solving. Candidates should be task-oriented; possess a positive, will-do attitude; have a desire for a long-term People Operations career; and have excellent interpersonal and communication skills. This role would be suitable for a professional with 2-5 years of experience.

What Will You Be Involved With?

• Contributing to the implementation of People strategies and initiatives aligned with the overall business goals
• Maintaining compliance with federal, state, and local employment laws and regulations, and recommended best practices; reviews policies and practices to maintain compliance
• Processing US multi-state payroll and all applicable payroll reporting via Rippling
• People administrative tasks, including but not limited to maintaining accurate and up-to-date employee data in our Human Resources Information System (HRIS). This includes processing new hires, terminations, promotions, leaves, and other changes in status.
• Leading a seamless onboarding process for new hires, including preparing new-hire paperwork, coordinating with IT, and scheduling orientation sessions. (I-9s, background checks, tax forms, etc.)
• Administering performance review cycles (distributing forms, tracking completion)
• Responding to employee inquiries on policies, benefits, and procedures
• Assisting with annual US Open Enrollment
• Assisting with mergers & acquisitions
• Building monthly reports as well as reports for TT leadership
• Standard US compliance reporting, such as EEO-1
• Nurturing a positive working environment 
• Annual handbook launch and harassment training 
• Assisting with FMLA & leave 

What Will You Bring to the Table?

• 2-5 years of previous experience in an HR role.
• Bachelor’s degree in Human Resources, Business Administration, or related field
• Strong knowledge of HR processes, best practices, and labor laws.
• Exceptional organizational skills and attention to detail.
• Must be a team player with a strong desire to learn.
• A people person with excellent written and verbal communication skills.
• Able to work with team members across multiple time zones. 
• Ability to learn and adapt to ever-changing policies and procedures.
• Ability to handle confidential information with discretion.
• A motivated individual able to take initiative, manage time, and prioritize tasks.
• Proficiency with HRIS Systems,  experience with Rippling is a plus.
• Proficiency in G-Suite (Google) and Microsoft Office applications is a plus.
• PHR or SHRM-CP certification preferred but not required.

What We Bring to the Table

Competitive Benefits & Perks We offer a comprehensive benefits package designed to support your well-being, growth, and work-life balance.

• Health & Financial Security:
  • Medical, Dental, and Vision insurance
  • Flexible Spending Accounts (FSA) & Health Savings Accounts (HSA)
  • 401(k) retirement plan
  • Pre-tax transit and parking benefits
• Time Off & Flexibility:
  • Enjoy the best of both worlds: the energy and collaboration of in-person work, combined with the convenience and focus of remote days. This is a hybrid position requiring three days of in-office collaboration per week, with the flexibility to work remotely for the remaining two days. Our hybrid model is designed to balance individual flexibility with the benefits of in-person collaboration, enhanced team cohesion, spontaneous innovation, hands-on mentorship opportunities and strengthens our company culture.
  • 22 days of Paid Time Off (PTO) per year, with the option to roll over unused days.
  • One dedicated day per year for volunteering.
  • Two professional development days per year to allow uninterrupted professional development.
  • An additional PTO day is added during milestone anniversary years.
  • Robust paid holiday schedule with early dismissal.
  • Generous parental leave for all parents (including