FinTech Female Fridays: Meet Alexa Catalano, Vice President, Strategy and Operations at Venn by Two Sigma

Not every career journey follows a straight line—and Alexa's certainly didn't. She began in the world of fashion, working in product development and production, but soon realized that the fast-paced, high-pressure environment wasn’t aligned with her long-term vision of financial independence. So, she pivoted. Her leap into tech began with a startup that was, as she describes it, “like Tinder for M&A.” There, she got to wear many hats—client success, marketing, strategy—and discovered a love for solving complex problems and driving operational growth. Today, she continues this passion in a more scaled setting, where she leads strategy and operations at a larger firm.

Alexa currently works at Venn, an advanced investment analytics platform powered by the quantitative force of Two Sigma. The company sets itself apart by combining cutting-edge data science with a culture that embraces curiosity and diversity of thought—only about half the employees come from traditional finance backgrounds. “That kind of balance brings a richness to the work,” Alexa says. “And the friendly, inquisitive culture makes it even more rewarding.”

In terms of her impact in FinTech, Alexa’s influence may not always be loud, but it is deeply meaningful. She actively champions junior employees, especially when they’re not in the room—something she benefited from earlier in her career. “Mentorship doesn’t always look like formal meetings or long emails,” she explains. “Sometimes it’s just making sure someone’s name gets brought up in the right conversations.”

Her career is also defined by a relentless curiosity. She’s always raising her hand for new challenges, and that habit has made her the go-to person for projects that don’t have a clear owner. “Being seen as a trusted and competent voice in your company—one who welcomes ambiguity—can be a game changer for your growth,” she shares. It’s how Alexa’s carved out a unique path and earned the autonomy to shape her career trajectory on her own terms.

One piece of advice that stuck with Alexa?

“Humility is important, but don’t let yourself become invisible.”

 And when it comes to mistakes, she believes in transparency and accountability. “Everyone messes up. What matters is how you handle it,” she says. “Being open, honest, and quick to ask for help builds trust and respect.

More on Alexa

Where you currently live: New York

Living arrangement: 2bd/3bth Apartment

Family at home: Husband

Hometown: Atlanta,GA

Favorite hobby: Reading 

Favorite show to binge: Mad Men (annual rewatch)

What's the best job decision you ever made? 

Taking the leap from fashion to a startup! The “all hands on deck” environment provided me opportunities I wouldn’t have been exposed to in a more corporate / bureaucratic structure. It also allowed me to try on different hats and see what fit best for me and my skill set. 

Can you tell us about a time someone encouraged you to try a task or take on a project you didn’t think that you would know how to do/or be good at? 

My boss asked me to run the due diligence process for the largest deal our company had done at the time. I didn’t have any experience in project managing this type of thing and it was heavy in cybersecurity, which I knew nothing about. I learned so much throughout the process and built trust with people in the organization I wouldn’t have met had I not taken on the project. The project helped propel me to a new level in my career and ended up being a cornerstone in my promotion packet. 

Daily Diary 

8:30: Emails + Slacks

9:00 :Review Salesforce + Platform Dashboards

10:00: Focused Work

12:00: Lunch + Emails + Slacks

1:00:1x1s + Meetings 

3:00: Project Follow Ups

6:00: Review Schedule / Plan for Next Day + Iterate where necessary