Corporate: Caroline Paillou

Senior Corporate Counsel, Oracle

St. Louis

As senior corporate counsel at the software company Oracle, Caroline Paillou always tells the business teams that she is most successful when she turns around a relationship that is “looking like it might go sour” and instead establishes “a long, successful relationship.”

Paillou now works to avoid litigation, but when she started at Washington University School of Law, she wanted to be a prosecutor. Her father was a police officer, and “that was a lot of the exposure I had to the law,” she said.

She interned for the St. Louis County prosecuting attorney after her first year and loved being in the courtroom but “took the work home with me mentally” and determined that she needed to pursue a different area of law, she said.

Before joining Oracle, she worked at Greensfelder, Hemker & Gale and assisted clients in financial services. She also chaired the firm’s gift drive in support of Motion for Kids, a Bar Association of Metropolitan St. Louis holiday event that provides gifts to children who are in the foster care system or have been severely impacted by the criminal justice system. 

She would coordinate the firm’s gift giving, which was time-consuming, she said. Each year, they sponsored more than 100 kids.

“I was driving around with bikes hanging out the back of my car through the majority of December while also desperately trying to bill hours towards the end of the year,” she said.

At Oracle, she has had to learn about artificial intelligence, and sometimes, she needs to “learn how the widget works,” she joked.

To ensure she understands a field as challenging and new as AI, “you have to be unafraid to ask what sometimes appears to you to be a stupid question because if you have that question, lots of people in the room” do too, she said. “The only way to be successful is to ask questions, ask questions, ask questions, until you have a level of confidence that you know what you need to know to provide the advice [a person] is asking for.”