Alicia Dagosta Can Finally Be Herself

By BILLY YOST

Alicia Dagosta decided a change was in order. After twenty-three years of straitlaced and traditional professional dress, the vice president, assistant general counsel, and head of regulatory legal at Oportun finally felt ready to just be herself. “Being here finally made me feel like I could be the real me, and in this case, that meant being able to wear my Prince t-shirt to work and shaving half of my hair,” the lawyer says, laughing.

The trendy side cut, one much closer to the hairstyle she wore in her preprofessional years, is a celebration in and of itself. Her years spent rising up through firms and large organizations like JPMorgan Chase brought a great deal of success, but the lawyer always felt like some part of her was being sacrificed in the process.

“Whether it was my experience in law school or in my previous roles, I’ve always felt a little bit like a fish out of water,” Dagosta admits. “It always seemed like there was a mold I was trying to fit myself into, and when I came here, I couldn’t believe there was a place like this where I could just be me, truly me.”

There’s no accounting for what feeling like one’s true self is worth in the workplace. And it’s a feeling Dagosta wants to flow freely through her team. It’s not about a dress code, it’s about the kind of environment where regardless of one’s background or experience, their opinion is valued, respected, and allowed to compete in the marketplace of ideas. To the lawyer, and to anyone willing to take the time to read virtually any study on the subject, diversity of opinion and background makes an organization stronger.

Alicia Dagosta shares how Oportun’s collaborative culture lends itself to her success as a lawyer:

“You just have to look at the people here to understand what is valued,” Dagosta says. “One of our core values is care, and that is truly exemplified every day at work. It may seem strange, but I notice it most in the way that we can disagree with each other about the decisions that we make. It’s not just about the bottom line and where the law intercedes. It’s always so apparent that people are looking at the bigger picture and considering the impact on employees and our customers. It’s such a different way of looking at things than I have seen in my career previously.”

Dagosta clearly remembers being told earlier in her career that she was too forthcoming with her emotions. In a vacuum, she says the advice is understandable, but in the situation, the lawyer was being told to shut down the portion of her practice that is incredibly important for any in-house practitioner: humanity.

“It’s always so apparent that people are looking at the bigger picture and considering the impact on employees and our customers.”

Alicia Dagosta

“You don’t need to let everyone know just how bad your day is,” Dagosta jokes. “But it’s perfectly okay to let the people around you know that you might be having a hard time and need a little extra help, or that you’re incredibly proud of your kid’s accomplishment. That’s part of being a human being, and I don’t think that needs to be turned off when you come to work.”

When it comes to acting in a position of leadership, Dagosta admits she’s never loved a hierarchy, or as she puts it, “being a boss.” While the lawyer says her husband would disagree with that statement, when it comes to her law practice, Dagosta has found comfort in Oportun’s much flatter organizational style.

The lawyer emphasizes that law is rarely black and white, and she requires her team to work collectively to find creative solutions in order to help Oportun grow. Dagosta says she’s experienced enough to know that fear or uncertainty rarely produces the best results, which is why her team is always encouraged to offer new ideas and approaches.

“I couldn’t believe there was a place like this where I could just be me, truly me.”

Alicia Dagosta

Dagosta is still actively working to break down barriers.

“The other day I had to call someone who was technically a number of levels down from my role, and I could hear that this colleague of mine was really nervous in speaking with a VP,” she recalls. “I can understand how that might be nerve-wracking, but I think it’s important to take the time to explain that I just wanted their expertise on a situation, and that I welcomed their feedback. The environment here is one that encourages people to speak up, and I want that felt on my team as much as anywhere else in the company.”

Dagosta may not be the traditional attorney. Her son turned her into an automotive enthusiast, and her family regularly enjoys car shows. While she has wanted to be a lawyer since the age of eight and loves what she does, if she ever decided to change careers, she’d be redecorating houses for families on HGTV. But all of these things make her who she is, and she isn’t afraid to let it inform the person she is at work. Because for the first time, Dagosta can be her whole self at Oportun.