By Jessica Darmoni
“I have built genuine trust and strong relationships with my team here at Citadel, which go beyond the day-today work,” says Jeanine Oliva, Global Head of Tax Operations at Citadel and Treasurer of WILD Gives Back. “Taking the time to get to know team members as individuals deepens trust, fosters collaboration and in my experience, high performance naturally follows.”
The Glass Hammer sat down with Oliva to learn more about her path to one of the world’s most demanding financial firms. It was not shaped by a master plan but by trusted relationships, a relentless work ethic and a refusal to let self-doubt have the final word.
Impactful Connections
Oliva has always been in roles that support middle and back office operations by understanding how global transactions are taxed. Her path to Citadel first emerged while she was a public accountant at RSM McGladrey.
“I was working with a close friend when he left to join Citadel,” says Oliva. “Soon afterwards, I was hired by a hedge fund administrative company that at the time was owned by Citadel.”
It was through this role that Citadel became one of her clients. The proximity gave her first-hand insight into the company’s culture.
“I saw their high standards and approach to excellence up close,” she explains.
Those qualities did not intimidate her but instead drew her in. She had kept in touch with her former colleague from McGladrey and when the opportunity presented itself to work at Citadel, she was ready.
The Human Endeavor in Leadership
“Being trusted as a leader at Citadel is one of my greatest motivators,” she says. “However, what really sustains my day-to-day are the people.”
This philosophy extends beyond her immediate team. She describes keeping in touch with former colleagues over the years, offering support in the form of a fresh perspective on a tricky problem, or a job reference at just the right moment.
Oliva is also the Treasurer of WILD Gives Back, a not-for-profit 501(c)3, which raises funds for students to study derivatives courses at the Associated Colleges of Illinois. She has a unique perspective from her vantage point.
“Some of the most meaningful moments in my career have been watching people I’ve worked with grow into their full potential,” she reflects.
The Value of Being Seen
Oliva thinks back on her career, which was more of a game of chutes and ladders, than a direct climb to the top. She describes a pivotal moment when early in her career, and pregnant with her first child, a former boss tried to bring her back to his team. She raised a concern that it might not be practical timing and his response has stayed with her ever since: “Half of Jeanine is better than no Jeanine.”
His comment was a critical reminder that genuine professional relationships are not transactional. For a woman in finance, navigating a career alongside pregnancy and motherhood, being told plainly that her presence was valued regardless of circumstance was a message that carried real weight.
Making Space
Oliva points to Harlan Ten Pas, lead partner of the Financial Services team at McGladrey, as another significant influence, shaping not only the early years of her career, but also her leadership.
“He was exceptionally sharp and always approachable, regardless of his seniority. He took a personal interest in each member of his team creating an environment where many colleagues felt like family.”
That mattered especially in the early years, when she was often one of the only women in the room.
“His warmth and investment in his people showed me that belonging was possible in a field that didn’t always make space for me.”
He also modeled something she values deeply. She says he taught her “that a successful career and a fulfilling personal life aren’t mutually exclusive.” Though he passed away last year, his influence continues to shape how she leads.
Turning self-doubt into fuel
While Oliva is secure in her industry knowledge, that does not mean she is not faced with moments of uncertainty.
“When resistance arises in a meeting, I lean into it rather than away,” she says. “At Citadel, being entrepreneurial from day one and challenging ideas constructively and constantly asking, “is there a better way?” is not just permitted, it’s expected.”
When self-doubt surfaces, her response is characteristically grounded because she doubles down on the work. This could mean reading up on recent regulations, talking through issues with colleagues, or building her understanding until she is confident.
“At Citadel confidence comes from knowledge, rigor, and continued curiosity, not complacency.”
A Human Mind Behind AI
Even when it comes to modern technologies such as AI and Machine Learning, Oliva believes the human element will still be an important one.
“Technology, including AI, is only as good as the human mind behind it,” she says.
In an era of rapid AI adoption in finance, this stance feels more relevant than ever. Questioning outputs and challenging existing processes, are not just encouraged at Citadel but expected. The culture of continuous improvement is something she genuinely values, and something she sees as essential for the next generation of leaders.
One of the most practical pieces of guidance Oliva carries is a healthy skepticism of doing “the same as last year.”
“The principle is straightforward,” she says. “Don’t accept inherited processes at face value. Rules and fact patterns can change. Understand the calculations. Know where the data comes from. Do the research.”
Leaders in a Crowd
When she thinks of the young women only starting out, she says, “Keep pushing toward what you want. Persistence and hard work generate dividends. Don’t be afraid to take a different path to get there, and if others doubt you, prove them wrong.”
She believes the leaders of tomorrow will be defined by the strength of their personal relationships and the ability to trust their own judgment.
“Relationships keep you grounded, keep you motivated, and open doors,” she said. “Critical thinking, the capacity to reason beyond what any algorithm can offer, is what ultimately distinguishes a leader from the crowd.”
It’s a vision of leadership that’s both deeply human and rigorously disciplined, which sounds a lot like Jeanine Oliva.
