Kelsey Cooling
Kelsey Cooling is a Senior Project Manager with approximately 10 years of experience leading enterprise transformation initiatives at the intersection of business operations, technology, and regulated financial services. Based in Bonita Springs, Florida, she specializes in delivering high-stakes programs across mortgage servicing and telecommunications environments, where precision, cross-functional coordination, and regulatory compliance are critical. She is known for stepping into complex, at-risk initiatives and stabilizing them through structured governance, stakeholder alignment, and clear execution strategy.
Throughout her career, she has led large-scale, high-impact programs involving significant financial and operational complexity. Her portfolio includes preserving $7.5M in monthly client revenue by coordinating over 100 stakeholders on a critical payment portal initiative, managing a $172.5M subservicing acquisition covering approximately 1.97M loans, and executing an 840 TB enterprise data migration with zero business disruption. She has also driven compliance-forward initiatives, including resolving over 100 audit-related findings ahead of a CFPB review, and has supported multi-hundred-million-dollar integration and rebranding efforts across major enterprise systems and organizations.
Her leadership approach is grounded in clarity, trust, and human-centered execution. She emphasizes aligning large teams around measurable outcomes while translating complex technical and operational work into decision-ready strategies for executives and board-level stakeholders. Recognized as a True Blue Award recipient at Cenlar FSB
, she is valued for her ability to bridge technical delivery with business impact, foster cross-functional collaboration, and guide organizations through transformation with transparency, adaptability, and consistent results.
• North Central College - BS
• Relay Award - Project Resolute
• True Blue
• It's a Pittie Rescue
What do you attribute your success to?
I attribute my success to a combination of adaptability, creativity, and relationship building, grounded in a human-centered leadership style that emphasizes transparency, humor, and honesty to build trust. I’ve found that people navigate change more effectively when they feel connected, respected, and included. I’ve also been fortunate to learn from strong female leaders in both my personal and professional life, including my sisters Katie and Jill, as well as mentors like Karen Roarkemper, Leslie Teeler, and Kelly O’Donnell, who each played a key role in shaping my growth and ability to lead in complex, cross-functional environments.
What advice would you give to young women entering your industry?
My advice to young women entering this industry is that your greatest asset is simply being yourself. Early in my career, I felt pressure to fit a certain mold, especially in corporate and technical environments, but I’ve since learned that authenticity is far more powerful. The people who stand out are not those who appear overly polished or rigid, but those who bring their full personality—humor, humanity, and authenticity—into their work. Staying true to who you are will take you further than striving for perfection ever will.
What are the biggest challenges or opportunities in your field right now?
One of the biggest challenges in my field is managing complex, cross-functional enterprise programs and navigating large-scale change across diverse stakeholders. At the same time, this presents a significant opportunity to improve outcomes by taking a more people-centered approach—focusing on connection, respect, and inclusion throughout the change process to drive greater alignment, engagement, and success.
What values are most important to you in your work and personal life?
The values most important to me in both my work and personal life are authenticity, transparency, humor, adaptability, creativity, and relationship-building. These guide how I lead, collaborate, and show up for others, and they help me build trust, navigate change effectively, and foster strong, meaningful connections.