Digital Operations Associate Jobs in Chicago, IL

OppFi is a leading tech-enabled digital finance platform that works with banks to provide financial products and services for everyday Americans. Through a transparent and responsible platform, which includes financial inclusion and excellent customer experience, the Company supports consumers who are turned away by mainstream options to build better financial health.
We are a team of caring, innovative, and inclusive individuals who thrive in being immersed in diverse talents, expertise, perspectives, and backgrounds. Our employees approach every new challenge with an unparalleled ability to see what could be rather than settle for what is. Our business principles guide us and create an open and collaborative culture where we improve 1% every day, and the best ideas always win! We welcome individuals who want to make an impact in the financial system by facilitating credit access, expanding financial inclusion, promoting financial health, and delivering exceptional customer service.
A few other fun facts about us. OppFi is one of the top consumer-rated financial platforms online, maintaining a 4.4/5.0-star rating on Trustpilot. We are a 2025 Crain's Fast 50™ company and were named on Built In's 2026 Best Places to Work in Chicago.
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.

Total Rewards and Benefits:
At OppFi, we are committed to fostering a fair and equitable workplace. The compensation range for this role reflects our good faith compensation estimate for this position. Final offers are determined based on a myriad of factors including, but not limited to experience, skills, qualifications, and other relevant business considerations. Candidates are encouraged to discuss compensation expectations during the hiring process. In addition to base pay, the total compensation package includes eligibility and potential for performance-based bonuses and equity grants dependent upon the role and job level.
OppFi offers a flexible, remote environment, 401(k) matching program, and generous paid time off. Other benefits include medical, dental, and vision coverage, and tuition reimbursement. Additional benefits include DoorDash DashPass, Figo pet insurance, Rocket Lawyer, and access to LinkedIn Learning. OppFi also offers Fringe, a lifestyle benefits platform that allows employees to decide how to spend rewards from dozens of vendors like Uber, DoorDash, and UrbanSitter. #LI-Remote
Compensation Range:
$46,792-$77,208 USD
EEO Statement:
OppFi is an equal opportunity employer and does not discriminate based on any actual or perceived legally recognized protected bases under local, state, federal law, or regulations. Our goal as a company is to build an equitable workplace that actively works to dismantle systems of oppression in our processes, procedures, and interactions. We aim to help our employees thrive where they work and beyond.
As part of OppFi's commitment to providing equal opportunity to qualified individuals, OppFi will ensure that persons with disabilities are provided reasonable accommodation as defined by applicable laws and organizational policies. If reasonable accommodation is needed to participate in the job application or interview processes or job requirements, please contact our People Team at recruiting@oppfi.com.
Pursuant to the requirements of the California Consumer Privacy Act, OppFi is providing the "OppFi California Employee Privacy Policy", which details the categories of personal information collected and your rights under the policy. If you are a California resident, please review the policy here: https://privacy.opploans.com/policies?name=california-disclosures-and-privacy-policy
The information in this document is for general informational purposes only. It is not intended to be an all-inclusive list or description of the organization and its requirements for positions and employees. OppFi reserves the right to modify or change the information on this document at its discretion.