Aileen Chou Enables Massive Milestones for Oportun

There are several reasons why Aileen Chou made the decision to join Oportun in March 2018. The current senior director and corporate counsel had spent the previous seven years in firms from Hong Kong to New York doing IPOs, securities offerings, and other corporate transactions. But she never got to see that work from its conception to its execution.

Oportun seemed like a promising private company that Chou could grow alongside. Moreover, she liked the atmosphere. “This place seems to draw in certain people,” Chou says, searching for the right words. “I don’t know how else to explain it. The people here are just so nice. Everyone is trying to be a good person. It’s something you notice right away.”

The mission and culture at Oportun continue to enable the company’s growth. The evolution of the company necessitated the legal team to take on new work—including the transition into a public company and Oportun’s first-ever strategic acquisition.

Today Is the Day

When Chou first arrived at Oportun, she heard plans that she was familiar with: the company would eventually go public. She didn’t think much of it at first. Most successful private companies have plans to go public, Chou explains. Because she had not heard about a timetable, she was convinced it wasn’t something that would happen soon.

“Then I walked in one day and was handed some old prospectuses and told that it was time to start working on the IPO,” Chou remembers, laughing. The small legal team had their work cut out for them. But Chou was ready to roll up her sleeves and draw on her extensive IPO experience.

In 2019, it was all hands on deck and the small but mighty legal department needed to extend far outside its comfort zone to make the deal happen. That kind of situation is exactly why Chou went in-house in the first place.

“I’ve always been more business-minded and being in-house counsel gives you the opportunity to get your hands dirty as much as you want,” the lawyer explains. “Everyone’s a little bit underwater at all times, so everyone is always receptive to an offer to help or a new perspective.”

There was another plus that isn’t always common for in-house legal departments. It was clear upon Chou’s arrival that the legal team was respected and trusted. No matter the issue, legal is at the table.

The long process was an exciting one. For many people, an IPO is a once-in-a-career experience and Chou had more than a front row seat, she was on the court as a major player.

As most companies learn, the IPO is the beginning of the journey, not the end, and there were numerous challenges ahead for Chou.

Complicated Deals on Tight Timelines

Oportun’s first major M&A deal would be completed at the end of 2021. The company acquired neobanking platform Digit (with roughly one hundred employees) for approximately $212.9 million—an essential step for Oportun to continue elevating and expanding its products and building a combined platform that helps individuals improve their financial health.

“I’ve worked on really large offerings and deals in Europe and Asia and while the dollar value was higher, none felt as intense or important as doing a deal in-house,” Chou says. “There were a lot of negotiations, and the timetable was truncated. We signed the letter of intent in mid-October, signed the acquisition agreement in November, and closed the deal right before Christmas. It was pretty intense.”

Yet again, the in-house role mandated stretching beyond the realm of the legal department and Chou was involved from the due diligence, agreement negotiations, closing mechanics, and post-deal integration.

It was an opportunity to see M&A from beginning to end, and it’s yet another first that Chou has helped the company reach.

Hitting Goals and Setting Baselines

Chou’s wide breadth of responsibility also includes expanding and better defining Oportun’s already strong corporate responsibility efforts. The company donates one percent of its annual profits, but Chou says Oportun is seeking to start tracking their efforts better when it comes to corporate social responsibility (CSR) goals.

“The thinking is that if we’re going to report on these efforts, then we need to be held accountable and make sure we’re tracking our CSR goals,” she explains. “That could be figuring out how many pounds of paper we’re saving by moving to applications like DocuSign or how diverse your leadership team is. If you want to demonstrate growth, you need to be know what your numbers are.”

Outside the office, Chou has been an active board member of the Asian Law Alliance for the past four years. The organization has been critical in voter registration and providing monthly housing law clinics in Santa Clara County, along with fundraising and pro bono work.

”As an immigrant, I saw firsthand how confusing and overwhelming the US legal system or laws can be for new immigrants with limited English skills,” she says. “I’m grateful to organizations such as ALA who stand up for the voiceless and empower them in their time of need.

Chou, an avid meditator and motivated reader who is currently working her way through Shakespeare’s entire works, says the mission of Oportun and the culture that seems to almost feel like a nonprofit is essential to keeping her life balanced. Whether it’s another acquisition or Henry IV, Chou is looking forward to another year of challenges with a team she knows she can rely on.

Know Your Strengths, Manage Your Weaknesses

As a legal leader at Oportun, Aileen Chou is heavily invested in making sure her team feels empowered to keep growing. For those earlier in their careers, Chou advocates being mindful of one’s strengths and continuing to develop eareas that need more improvement.

“Find what your strengths are and double down on them,” Chou says. “For me, it was getting technical and getting lost in financials and how our business operated. My biggest fear was speaking in large groups. I would turn bright red. But there are so many things you can do to mitigate your weaknesses—don’t let them hold you back. Challenge yourself to feel uncomfortable and find people that support your growth.”