That Pivotal Moment of Change

Episode 20: Lorraine K. Lee on Showing Up, Standing Out, and Speaking with Impact

What does it take to build a personal brand that opens doors—and still feels authentic? In this episode of That Pivotal Moment of Change, Lorraine K. Lee shares her journey from editorial leader at LinkedIn and Prezi to keynote speaker, LinkedIn Learning instructor, and author of Unforgettable Presence. We talk about navigating pivotal moments like layoffs, embracing the power of introversion, and making the leap from middle management to senior leadership. Lorraine offers powerful frameworks like EPIC (Experiences, Personality, Identity, Community) and RAVE (Relationships, Appearance, Visibility, Expertise), and opens up about the mindset shift that changed her career: becoming the CEO of your own growth. Whether you're early in your career or leading a team, this episode is packed with actionable advice, empowering stories, and sharp insights on how to show up more intentionally in your work.

Episode 19: Roger Rohatgi on Hustle, Heart, and Human-Centered Innovation

In this episode, Roger Rohatgi shares the remarkable journey that led him from designing rave flyers and producing an award-winning film to becoming Chief AI Officer at Chai. Roger opens up about how building an app to help children with autism sparked his entry into the AI space, and how he’s stayed grounded in empathy and purpose while leading design at scale for companies like BP, Objective Edge, Ministry Brands, and more. He talks about launching the first social television network in the U.S. after pitching a wild idea just weeks into a new role, and why curiosity, confidence, and an ever-present hustle have guided him through each chapter of his career. We also explore the rise of synthetic users, the future of UX in an automated world, and the simple but powerful mantra that’s kept him going: “Change is the only hope you have.” Whether you're a designer, technologist, or someone navigating transformation, Roger’s story is a masterclass in embracing change—and shaping what comes next.

From Personas to Purpose: Kevin Hawkins on Strategic Leadership

In this episode of That Pivotal Moment of Change, Kevin Hawkins shares a thoughtful look at his evolution from building products to building high-performing teams. Reflecting on experiences that span from fintech startups to global travel platforms, Kevin opens up about what it really takes to scale teams—from 6 to over 100—and the mindset shifts that come with it. One of the most compelling ideas in this conversation is Kevin’s use of stakeholder personas—a concept that applies product thinking not just to users, but to the people around the product. By understanding stakeholders’ motivations, fears, and communication styles, Kevin builds trust, aligns strategy, and leads with intention. We also explore his transition from individual contributor to people leader, the tension between coaching and directing, and the clarity that comes from leading with empathy over ego. Whether you're growing a team, stepping into a new leadership role, or rethinking how you build influence, Kevin’s story offers clarity and inspiration for the journey ahead.

Tim Gilligan: From Backstage to the Boardroom, Designing Operations with Heart

In this episode of That Pivotal Moment of Change, I sit down with Tim Gilligan, whose career has taken him from immersive theater productions in New York to the world of design operations at Capital One. Tim’s story challenges the idea of linear career paths and explores how each chapter—no matter how unexpected—can become a powerful building block. We talk about the transition from stagecraft to systems thinking, the importance of resilience as a resource rather than a mindset, and the value of asking for help when the way forward feels uncertain. Tim opens up about learning to close chapters without clean endings, how community and coalition-building have shaped his leadership, and why storytelling remains central to his work. This is a conversation about integration over reinvention, purpose over titles, and how the most meaningful careers are often the ones we never saw coming.

Draw the Rectangle: Matt Walsh on Resilience, Reinvention, and Leadership

In this episode of That Pivotal Moment of Change, we sit down with Matt Walsh — Founder & CEO of Greenstone and a veteran behind some of the most iconic digital agency work of the last two decades. Matt takes us back to where it all began: sitting at his desk on day one of his UX career, staring at a blank screen, unsure of what to do next — until he simply drew a rectangle and took the first step. From that moment forward, Matt shares the pivotal decisions that shaped his career — from playing a key role in digital strategy for brands like Nike and Domino’s, to navigating the highs and lows of big agency life, to ultimately leaving it all behind to start his own agency from scratch, in his basement. This conversation is packed with real, hard-earned lessons on resilience, curiosity, and the courage to reinvent yourself when the road ahead feels uncertain. Whether you're just starting out or a seasoned leader looking for what's next, Matt’s story is a powerful reminder that sometimes, the hardest part is simply getting started.