People Operations Associate - Benefits & Engagement

What you get to do:

Champion Culture through Engaging Events and Program Initiatives

• Support cross-functional planning and execution of high-impact employee programs (e.g., Thrive Where You Work Week, Annual Kick-Off, EOY celebrations, Belonging@OppFi programming, Town Halls, and recognition initiatives).
• Provide extensive on-site support for company-wide events in Chicago
• Manage remote hotel room block requests for departmental onsites.
• Contribute to ideation and execution of new engagement opportunities that foster company culture across in-person, remote, and hybrid experiences.
• Own event vendor processes, including securing quotes and COIs, contract reviews, and vendor onboarding.
• Collect and analyze employee feedback to evaluate event effectiveness and inform future strategy.
• Serve as primary contact for Belonging@OppFi BRG groups, coordinating meeting schedules, program approvals, vendor coordination, resource sharing, and internal communications.
• Facilitate the selection of Belonging@OppFi/BRG-aligned charitable partners through OppFi’s charitable partner framework for annual giving.
• Coordinate and participate in the Belonging@OppFi new hire orientation presentation rotation.

Contribute to the Employee Communications Experience

• Maintain the company intranet through regular content updates and audits; facilitate platform training and new hire onboarding sessions to ensure team familiarization; advocate and support ongoing platform utilization, adoption, and enhancement.
• Draft and distribute internal announcements celebrating employee milestones, such as birthdays and work anniversaries.
• Support execution of internal communication plans, including content collection and development of digital assets and polished presentation decks.
• Oversee the Belonging@OppFi presentation schedule for new employee orientation and participate as a regular presenter in the rotation.
• Support the operational success of company Town Halls by providing comprehensive technical and logistic support for both in-person and virtual formats.

Contribute to the Employee Benefits & Perks Experience

• Process weekly recognition point distributions and maintain ongoing analysis of program utilization.
• Provide back-up for New Hire Orientation Benefits presentation.
• Provide operational support for:
  • Quarterly and annual vendor review processes, including vendor engagement to secure required documentation.
  • Annual Benefits Open Enrollment activities.
  • End of Year audit and reconciliation activities.
  • Tuition Reimbursement processing.
  • Benefit and wellness communication and education initiatives.
  • Execution of other benefits and perk programs and initiatives as needed.
  • Ad hoc projects as needed.

What you bring to the team:

• High School Diploma required; two or four-year college degree in Business, Human Resources, or a related field desirable.
• 3+ years of related administrative or project coordination experience, ideally within a People Operations or Human Resources environment.
• Foundational understanding of employee benefits, employment law principles, and core People Ops/HR processes.
• Strong time management, organization, and professional communication skills with the ability to tailor messaging for diverse audiences.
• Intermediate proficiency in Microsoft Excel or Google Sheets (v-lookups, pivot tables, formulas) to analyze program data.
• Intermediate proficiency with presentation and design tools (e.g., PowerPoint, Google Slides, Canva, or Adobe) to create presentations and digital assets.
• Demonstrated ability to plan, prioritize, and execute deadline-driven projects.
• Ability to partner effectively with third-party vendors to meet deliverables.
• Flexibility and the willingness to help where needed and build positive relationships.
• Problem solver with high standard of quality, strong initiative, proactive approach, and resourcefulness.
• High emotional intelligence and intellectual curiosity.
• Open and receptive to feedback and coaching.
• Ability to travel to the corporate office in Chicago for periodic onsite company events as requested/required.