How OppFi’s ‘Thrive Where You Work Week’ Brings Company Culture to Life

With culture hackathons, panel discussions and a lively summer bash, an annual “homecoming” offers OppFi’s distributed workforce to celebrate an inclusive and diverse team.

Written by Brigid Hogan
Published on Jan. 17, 2024
How OppFi’s ‘Thrive Where You Work Week’ Brings Company Culture to Life
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As OppFi’s team arrived at the Offshore Rooftop at Chicago’s Navy Pier for the company’s summer party, they walked into a space transformed. The company’s logo lit up the entrance, marigold and blue lighting cast a branded glow around the space and even the signature cocktails — a margarita and an “Opperol Spritz” — featured OppFi-themed garnishes. As the evening continued, colleagues flocked to the dance floor to enjoy music from the Chicago Players and congregated around food stations featuring everything from Chicago favorites to Mediterranean classics.

According to DEI Lead Dennis Dent, the party was planned more meticulously than most wedding receptions, but those details weren’t what he remembers most from the evening.

“To be able to stand next to someone while you’re waiting on lamb chops and say, ‘Hey, I’m Dennis, I’m new here,’ and create a connection is very valuable,” he said. “We also had a chance to see our leaders in a more relaxed environment and to enjoy spending time together as a team, which made it a perfect way to celebrate Thrive Where You Work Week.”


Branded entry lighting reads “OppFi” leading into Thrive Where You Work Week at Navy Pier’s Offshore Rooftop venue.


More than just an opportunity to showcase an upbeat and lively party, Thrive Where You Work Week is an annual anchor for OppFi’s focus on employee engagement and culture building. As a newer team member, the week gave Dent deeper insight into the company’s tight-knit relationships and people-first priorities — especially since he had an insider’s perspective on the events.

“This was my very first Thrive Where You Work Week, and I was invited to be part of the planning, which allowed me to hear all of the hype from past years but also shape this year’s event as well,” he said. “This supportive and collaborative approach even from the planning process speaks to OppFi’s culture, and then we are able to see those values truly come to life at the event. People you’ve worked with and partnered with virtually are able to engage so deeply together as we take an in-depth look at how we will move forward together as a company and thrive.”



With a mission of facilitating safe, simple and more affordable credit access, OppFi is a tech-enabled, mission-driven specialty finance platform that broadens the reach of community banks to extend credit access to everyday Americans. Through best-in-class customer service, transparency, responsible lending and financial inclusion, the company supports consumers, who are turned away by mainstream options, to build better financial health. 


As a long-time member of the planning committee, Executive Assistant to the Chief Operating Officer Chelsea Stiffler started thinking about Thrive Where You Work Week long before team members began arriving at OppFi’s Chicago headquarters or logging into virtual events from home offices across the country.

“It can feel like the Super Bowl of our year with the amount of planning, thought and intentionality that goes into the week, and at the end, we’re exhausted in the very best way,” Stiffler said. “But really, this is just one small window into how OppFi strives to build a holistic and supportive culture.”


OppFi team members gather at Thrive Where You Work Week.



Rather than the events of the week serving as simply fun employee perks, Thrive Where You Work Week instead focused on connecting back to OppFi’s larger cultural priorities.

“We’re committed to taking intentional steps each day to create a culture where employees really feel heard, valued, included and cared for,” Stiffler said. “We can't afford not to. Our employees are worth it, and we owe it to our customers to have a workforce that looks forward to coming to work every single day, is proud of the company that they work for and feels connected to our mission.”

“We owe it to our customers to have a workforce that looks forward to coming to work every single day, is proud of the company that they work for and feels connected to our mission.”


The seed for Thrive Where You Work Week was planted in OppFi’s transition to a remote-flexible work environment in 2020. As their ways of working began to shift, leaders saw the need to ensure employees were set up for success with equity of resources and support regardless of location, tenure, team or title, and grounded in a philosophy that would truly allow the team to advance personally and professionally.

Over time, Thrive Where You Work Week developed into a focused week of cross-functional culture building for the distributed workforce in Chicago. The team began to look forward to the week almost as a homecoming or family reunion, with events that highlight OppFi’s mission and facilitate the opportunity for the team to connect holistically throughout the week, even outside the formal agenda hours.



Beyond the summer party, Thrive Where You Work Week featured a business resource group panel discussion to highlight OppFi’s diverse community, a culture hackathon to co-create ideas and solutions to improve employee experience, a speed networking event and a charity team-building event. Every event was optimized to include both OppFi’s onsite participants and those who participated virtually. “People want to be heard,” Stiffler said, “and so it’s crucial that our events give people genuine space and opportunity to talk and listen.”


As a newer team member, those informal connections offered Dent valuable opportunities to connect with team members he was meeting in person for the first time.

“Of course, I got to meet people from my team, but I also had the chance to meet those whose paths I would not necessarily have crossed in my day-to-day work,” he said. “Those organic, casual conversations with people across teams and of different tenures really help to build OppFi’s inclusive culture. As a DEI practitioner, I work to create an inclusive environment, and this week made it clear to me that OppFi is not a club or a clique. People can bring their true and authentic selves to share their talents at OppFi, rather than adjusting their skills and qualities to fit a mold.”


 Large letters reading “BRG” inside OppFi’s office signify a business resource group event, with team members standing nearby.


OppFi’s guiding business principles are more than catchy phrases that describe how good work happens in any office, according to Stiffler; the values provide the framework for building experiences like those Dent had at his first Thrive Where You Work Week.

“Our guiding principles are truly how we encourage employees to show up, and one of my personal favorites is ‘Best Ideas Win.’ We see it play out by pushing us to be curious, rewarding innovation and encouraging diverse perspectives,” she said. “I can’t help but think how many great ideas we would miss out on if employees operated on a belief that every voice wasn’t heard and empowered at OppFi.”



  • Define Success First
  • Best Ideas Win
  • Inspect What You Expect
  • Act, Then Optimize
  • Improve 1% Everyday


According to Dent, OppFi’s inclusion efforts are aimed directly at building a culture that makes it possible for the best ideas to win. As part of developing strong business resource groups, the DEI team took an in-depth look at OppFi’s demographic makeup and then spent time understanding where the company could invest additional support to enhance inclusion efforts.

“When I say inclusion efforts, I don’t mean a great strategy or strong definitions — I mean building actual communities where people can find their voices and safe spaces where people are able to go to leaders to express concerns,” Dent said. “Our business resource groups serve as a platform for education and awareness regardless of how individuals identify, allowing people to expand their knowledge and network across cultures and experiences.” 


OppFi team members cheer in outdoor rooftop setting with Chicago skyline in the background at dusk during a Thrive Where You Work Week event. 


Both Dent and Stiffler have found OppFi to be a perfect place to expand their own experiences as they grow personally and professionally, within the spaces created by Thrive Where You Work Week, in business resource groups and in their daily experiences.

Dent believes that others considering joining the company will find the same warm welcome and expansive possibilities that he did as a new hire. “There is space for you at OppFi, and there is also the support for you to grow and develop into a better, more impactful version of yourself,” he said. “Your career will absolutely be enhanced because the company is truly set up for you to succeed.”

Stiffler echoed his sentiments. “OppFi has been the best career move I have ever made,” she said. “I’ve grown and been challenged, but more importantly, I’ve felt so valued and cared for. If anyone is considering the company, I promise that they will not regret taking that leap of faith.”



Responses have been edited for length and clarity. Images provided by OppFi.

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