People Operations Associate - Benefits & Engagement

About the job:

The People Operations Associate - Benefits & Engagement will support key people initiatives through program facilitation, crucial administrative and operational support, and project coordination across employee programs including company events, internal communications, recognition, and the employee benefits experience. This position requires a proactive, organized, and detail-oriented individual who can manage multiple tasks effectively and contribute to a positive and productive work environment. With strong attention to detail, meticulous adherence to deadlines, and a collaborative mindset, this role will help drive successful program execution and employee engagement through thoughtful planning, flexibility, and cross-functional partnerships.  

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.