Dynamic Women & The Men Who Support Them – John O’Connell

John O’Connell is the type of leader that once you begin a conversation with him, you never seem to want it to end! His background is extremely interesting, and his support of women is truly second to none. Even the book that he penned is based on his daughters, and I can’t wait to dive into it, as it sounds fascinating. We are very grateful to John for his leadership and his support of women in the industry along his climb to success. He offers up some vital tips for young women entering into this amazing industry of ours. We are honored to share John’s story.

– Maree Moscati, CEO CTPRP

John O’Connell


The Oasis Group

Share how women influenced your career path.

John: I had my first female boss, Lisa Alter, when I worked at a company called Sybase, and she really helped me transition from being a technologist into selling technology and services. So in that way, she really kind of put me on my path.

I also actually followed her to another company, and we ended up being part of the leadership team that took the company public. Working under Lisa in a male-dominated industry helped me really understand that different viewpoints and different experiences enhance the development effort and can actually change the way the software works, which is the beauty of a diverse team.

Lisa also taught me that sometimes people have bad days, and from a sales perspective, that isn’t anything personal against you. She taught me to be tough in that way, but she also taught me to be really nurturing in another way.

She was a great leader, and she was one of those people who would really listen to what her team would say. She didn’t feel like she had all of the answers, and I took those lessons in leadership style with me throughout my career, all the way up to founding The Oasis Group, where we coach wealth management and technology firms and individuals.

What advice do you have for young women and men in this industry?

John: Well, for everyone coming into the industry, it is really important to network both inside and outside of your organization. Even those large firms may not be there forever, no matter how it seems today, and if all of your professional contacts are in your organization, you’re going to struggle.

For young women, it’s really important for you to find mentors and those allies in the room who will redirect when someone interrupts you, who will give you the respect that you deserve. They could be female allies or male allies, but if you’re just starting out, having someone who values your contribution to the company is critical. That’s who you want to align yourself with.

And going with that, my advice to men in the industry is to be that guy. You should be that guy who directs back to a woman when she is interrupted. You need to notice when that is happening and decide that it isn’t going to happen when you’re around. One person can make a huge difference in the dynamic of a room or a company, and you really should develop the mental fortitude to say something.

Tell us about your book and why you chose a female lead character.

John: The book is about a heroine who goes from being an individual investor to becoming an activist investor, which I think is something really relevant to young people today. They want to know what they’re investing in and how it can make a difference. It’s a narrative with teachable pieces in it, and the cast of characters are all inspired by people in my life.

The main character, Eileen, is based partly on my oldest daughter, who is a neuroscience ICU nurse working and living in Atlanta. But Eileen is also inspired a lot by my mom, her tenacity and her growth. My other 2 daughters are also in the book.

You mentioned you’re a gamer. What’s your console and favorite game?

John: I started on PC and had to move to XBOX after my PC had some issues. I love open world games, things like “The Witcher,” “Fallout 4,” and “Assassin’s Creed.” Those were huge for me.


John has more than 29 years of leadership experience in both emerging businesses and mature, established organizations. He started his career designing and developing financial applications at Merrill Lynch and KPMG Peat Marwick.

John transitioned from developing technology into sales and marketing while leading the financial services vertical for Sybase. John was a member of the senior leadership teams for several startups culminating in an IPO and packaging 2 other firms for their sale. He returned to Merrill for several years and until its acquisition in 2008. He held North American leadership positions at Oracle for over 8 years. He was the president of a private FinTech firm and held C-level customer facing roles at publicly traded InsureTech and FinTech firms. John founded The Oasis Group (www.theoasisgrp.com) in 2019.