Her Story
About Ashley
Ashley Willoughby, MBA, is a seasoned legal operations leader based in Pittsburgh, Pennsylvania, with nearly two decades of experience driving transformation across global corporate legal teams. She currently serves as Director of Legal Operations at Wabtec Corporation, where she leads strategic initiatives focused on operational efficiency, innovation, and the thoughtful integration of AI into legal processes. Her work centers on building scalable systems that improve alignment between legal departments and broader business objectives. Prior to her current role, Ashley spent several years in progressive legal operations leadership positions at Coherent Corp. She began her career in legal support and management roles, building a strong foundation in contract management, corporate governance, and process improvement. Ashley holds a master’s degree in organizational leadership and financial planning from Waynesburg University and a bachelor’s degree in business, legal studies, and philosophy from Gannon University. Throughout her career, Ashley has been recognized for her expertise in change management, legal strategy, and operational design, as well as her ability to lead high-performing teams through complex transformation. She serves as an advisory board member for Consero and is an active contributor to broader conversations around the future of legal operations. Above all, she is passionate about mentorship, continuous improvement, and fostering a culture where teams are empowered to innovate, adapt, and succeed—both professionally and personally.
Her Interview
Ten minutes with Ashley
01What do you attribute your success to?
I attribute my success to being relentlessly curious and never accepting 'the way we've always done it' as the best way. I've always been willing to challenge the status quo. I ask a lot of 'why' questions, focus on solving business problems, not just legal operational problems, and build strong relationships across functions. I've found that when you combine strategic thinking, operational discipline, and genuine care for people, you can drive meaningful change that lasts.
02What’s the best career advice you’ve ever received?
Don't be afraid to step into something new or difficult. I believe growth happens when you're willing to ask hard questions, learn continuously and focus on creating value for others. I've built my career by earning trust, delivering results and helping people see what's possible, not just what's familiar.
03What advice would you give to young women entering your industry?
Stay authentic—don’t feel pressured to conform to expectations that don’t align with who you are, because your perspective, voice, and integrity are exactly what will set you apart and make you successful in the long run.
04What are the biggest challenges or opportunities in your field right now?
Coming from a legal operations background focused on enterprise transformation, I see the greatest opportunity in building a connected legal ecosystem. Legal can't operation in a silo anymore. By integrating legal with compliance, procurement, HR, Finance, IT and the business, while leveraging AI and data strategically, we can deliver faster, more informed decisions while reducing risk. Legal operations is becoming the engine that connects strategy, technology, and execution across the enterprise. A challenge in my field right now would be the adoption buy-in pertaining to AI in legal. The challenge isn't the technology; it's the trust and change management. Lawyers are trained to mitigate risk, so before they are going to adopt AI, they need confidence that it's secure, accurate and aligned with their ethical obligations. Successful adoption comes from pairing the right governance with practical use cases, strong training, and executive sponsorship. When lawyers see AI as a tool that enhances their judgement rather than replaces it, adoption accelerates, which is why successful change management is crucial.
05What values are most important to you in your work and personal life?
The values that guide me most are integrity, curiosity and service. I believe in doing what's right, even when it's difficult. I'm naturally curios, so I'm always looking for ways to improve, innovate and learn. And I measure success by the impact I have on others, not just the results I achieve.
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