This year marked the fifteenth anniversary of HIA-LI’s Women’s Leadership Conference, a tradition that began after a roundtable convened by U.S. Senator Kirsten Gillibrand at Anne Shybunko-Moore’s company, GSE Dynamics. At that first meeting, we talked candidly about pay equity, childcare, work–life blending, and the headwinds women often face.

Senator Gillibrand encouraged us to keep the conversation going — and for fifteen years we have done exactly that, thanks to the leadership of our Women’s Collaborative, chaired by Carol A. Allen, President and CEO of People’s Alliance Federal Credit Union and HIA-LI Board Member, who has helped guide this event’s evolution.

This year, before introducing our keynote, I shared a moment early in my own career. When my boss at Dale Carnegie Training announced his retirement and asked me to step into the managing director role, I immediately began listing the reasons I wasn’t ready. He cut me off. He wanted to talk about why I was ready. I went home, barely slept, and finally allowed myself to imagine what could happen if I said yes. I did — and that decision changed the trajectory of my career.

As I told the audience, we gathered not just to talk about being fearless, but about what it means to do things afraid. Because, truly, “we were built to never stay in the shallow end.”

A Keynote on Authenticity and Possibility

Our keynote speaker, Clare Cusack, President and CEO of the New York Bankers Association, reminded us what becomes possible when leaders show up as their full, honest selves. A lifelong Long Islander and the first woman to hold her position in the association’s 131-year history, Clare spoke about her unconventional path and the power of embracing it.

One of the most moving moments came when she shared the story of a dancer who lost her leg in the Boston Marathon bombing and later trained to run the marathon on a prosthetic limb. On the night before the race, the dancer found a quote that carried her forward:

“No one is cheering louder for me than the woman I used to be. If that girl could see me now, never forget how wildly capable you are.”

Clare added, “Never forget how wildly capable you can be. Cheer for the future woman, too.”

Fear, Focus, and the Courage to Lead

Our panel, moderated by attorney Domenique Camacho Moran, a partner at Farrell Fritz, turned that message into practice. Each leader shared a moment when fear met purpose — and purpose won.

Teresa Ferraro, President and CEO of East/West Industries, reflected on leading a company whose mission is ensuring the safety of military aircrew. She spoke about listening as a core leadership skill, noting, “Two ears and one mouth — make sure you listen. It helps you stay focused and aware.”

Davi Tserpelis, Senior Vice President and Regional Business Banking Manager at City National Bank, described her defining quality in one word: tenacity. She shared how a difficult comment from a colleague once brought her to tears, until she later realized it was actually a recognition of her persistence. Then came a far greater trial: a breast cancer diagnosis shortly after starting a new role. She continued working throughout treatment, telling her children every day she would be okay. “I became — and stayed — very positive,” she said. “Now I get to inspire other women to be strong.”

Skye Ostreicher, founder of In the Room Media, talked about her unexpected shift from chemistry major to studying what she calls “human chemistry” — the reactions between leaders, organizations, and communities. She described losing a job during the pandemic, only to later build a platform that uplifts stories and voices that might otherwise go unheard.

Katherine Fritz, President and CEO of Long Island Cares, grounded the conversation in purpose shaped by experience. Growing up, her family sometimes relied on subsistence skills to stay fed — a perspective that drives her mission today. She also shared the bravest thing she has ever done: after losing her left foot in an accident, she spent years relearning to walk, then traveled alone to Europe to complete more than 200 miles of the Portuguese Coastal Camino.

Dawn Cagliano, President of IVCi, highlighted the responsibility leaders have to grow the people around them. Skills matter, she said, but emotional intelligence is what creates trust and followership. True leadership is measured not by individual achievements, but by how well others thrive because of you.

Throughout the discussion, Domenique emphasized the power of women speaking honestly — about ambition, uncertainty, and the moments that require courage. When women at different stages of their careers gather for open conversation, she said, clarity and confidence begin to rise.

Breakouts: Turning Insight into Action

This year’s conference also featured six breakout sessions designed to turn inspiration into practical strategy:

• The Success Equation: Multiply Your Potential Exponentially
• Level Up: Women Leading with Purpose
• Lead the Transformation — Navigating AI with Confidence
• Own Your Own Story: 20 Real Lessons for the Real World
• Built to Connect: The Undeniable Power of Women Who Choose to Collaborate
• The Triple Decker Sandwich Generation: Not Your Mother’s Estate Plan — Redefining Wealth, Caregiving, and Legacy for Today’s Woman

These conversations bridged leadership development, technology, storytelling, collaboration, and multigenerational caregiving — showing that women’s leadership is not one-dimensional. It is dynamic, evolving, and deeply interconnected.

The Message: Fearless Begins with Honest

If there was one thread binding the keynote, panel, and breakout rooms, it was this: women become fearless and focused not by eliminating fear, but by telling the truth about it — and choosing to move anyway. Leadership becomes possible when authenticity meets community, when lived experience becomes an asset, and when we cheer not only for the women we are, but the women we are still becoming.

The stories shared this year — about resilience, reinvention, caregiving, healing, entrepreneurship, and bold career choices — are proof that Long Island’s future is in capable hands. Our job now is to keep creating the spaces where women rise, support one another, and continue stepping out of the shallow end.