Emerson Taymor has worn many hats: designer, founder, investor, and entrepreneur exploring the intersection of design, product, and AI. In this episode, Emerson reflects on his path from scrappy freelance gigs in high school to co-founding the agency Philosophy, which grew into a 50-person consultancy before being acquired. He shares honest lessons from the trenches, including the grind of building momentum, the sting of layoffs, and the challenge of keeping quality high as you scale. Emerson also opens up about the power of partnership, the magic of foosball-fueled conflict resolution, and how staying resilient and curious has helped him navigate every pivot. From helping early-stage startups find traction to crafting toolkits that build trust in AI-powered products, his story is packed with practical wisdom. Whether you’re early in your career or a seasoned leader, Emerson’s perspective on experimentation, momentum, and making space for chance encounters offers a refreshing take on career growth in a rapidly changing world.
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In this episode, we go ringside with Andy Vitale - yes, literally. From professional wrestler to powerhouse design leader, Andy’s career path is anything but predictable. He shares how his early days in the ring taught him lessons in storytelling, empathy, and reading an audience—skills that now fuel his human-centered approach to design. We explore Andy’s journey through big-name companies like Office Depot, Rocket, and Truist, and unpack his perspective on mentorship, measuring design's impact, and the future of our craft in the age of AI. Along the way, Andy gets candid about being laid off, leaning into fractional work, and finding steadiness through uncertainty. Whether you're navigating a career pivot, leading through ambiguity, or just trying to make sense of design’s evolving role, Andy’s insights are real, relatable, and refreshingly grounded.
Michelle Parsons, Chief Product Officer at Lex and former product leader at Kayak, Spotify, Netflix and Hinge, joins That Pivotal Moment of Change for a wide-ranging conversation on product, leadership and personal growth.
She shares the story behind Lex’s bold pivot from a dating app to a thriving LGBTQ+ community platform—and what it really took to make that shift stick. From spotting early user signals to staying grounded in brand values, Michelle unpacks the decision-making behind a major product transformation.
We also explore the lessons she’s picked up throughout her career:
The power (and risk) of product pivots
Making room for growth, not just growth metrics
What she learned from taking on too much, too fast
Why great PMs focus on human connection, not just conversion
Whether you're early in your product career or leading at scale, Michelle’s insights are both practical and inspiring.
In this episode, Seth Carpien - Chief Growth Officer at Tricon Infotech - shares how “unintentional mentors” helped shape his career from finance to sales to product leadership. He reflects on the moment a colleague challenged his thinking and sparked a complete mindset shift - one that led him to embrace failure, stay humble, and treat his career like a product: something to test, learn from, and constantly improve.
We talk about navigating career pivots, leading remote teams, building cultures of curiosity, and why effort often matters more than talent. Whether you’re early in your journey or rethinking what comes next, Seth offers practical, candid insight on finding your path - and growing through the uncomfortable parts.
In this episode of That Pivotal Moment of Change, I sit down with design and operations leader Jose Coronado to talk about the moments that shaped his approach to leadership, growth, and building high-impact teams. Jose shares why he said yes to building a design operations practice from scratch - despite never having done it before, and how that risk became a defining moment in his career. We explore the importance of hiring for culture add instead of culture fit, the power of reinvention even without changing roles, and how intentional networking can start with something as simple as one conversation. Jose also reflects on a year-one failure that almost derailed everything - and the leadership lessons it taught him about patience, visibility, and scaling with purpose. Most of all, we talk about what it means to show up fully as yourself - and why authenticity, not assimilation, is key to building lasting impact.
In this live episode recorded at UXDX NYC, Prayag Narula - cofounder and CEO of HeyMarvin - joins That Pivotal Moment of Change to share how a career rooted in research led to an unexpected but impactful journey through entrepreneurship.
From building a demand generation startup without any sales background to founding Marvin, an AI-powered research repository that helps teams analyze and activate insights, Prayag reflects on the lessons, pivots, and hard truths that shaped his path. He opens up about the realities of leadership - how it’s more about showing up and doing the work than holding a title—and how being “pushed out” of his first company became the catalyst for building something more aligned with his values.
The conversation dives deep into the evolving role of researchers in an AI-driven world. Prayag discusses why bias can’t be removed but should be transparently addressed, how synthetic users can be powerful tools in the right context (though never a replacement for real people), and why AI isn’t coming for your job - but might be coming for the entry-level stepping stones that teach judgment and taste.
With sharp insight and refreshing candor, Prayag offers a thoughtful look at what it means to lead, adapt, and stay human in the age of automation.
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.
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.
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.
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.
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.
In this episode of That Pivotal Moment of Change, I sit down with Philip VanDusen, a creative visionary whose career journey is a testament to the power of reinvention. From his early days as a fine artist selling prints at street fairs to leading global design teams at Old Navy and PepsiCo, Philip shares how unexpected opportunities—and even setbacks—shaped his path. We explore why careers are more like webs than ladders, the importance of personal branding as a career safeguard, and how staying adaptable is key in an ever-evolving industry. Philip opens up about the challenges of burnout, the realities of ageism in design, and the lessons he’s learned from both the brand and agency sides of the business. He also dives into the role of trends, competitive research, and why embracing AI is crucial for the future of design. One of his biggest takeaways? "Dare to Suck." Philip believes that taking risks, failing, and learning along the way is the key to growth. Tune in for a conversation filled with hard-earned insights, career wisdom, and practical advice for anyone navigating change in their professional journey.
In this episode of That Pivotal Moment of Change, Uta Knablein, a seasoned product and design executive, shares the pivotal moments that shaped her leadership journey—from driving UX innovation at Nickelodeon to leading large-scale product strategies at JPMorgan Chase and iHeartMedia. She dives into the ripple effect of leadership, the power of continuous learning, and why adaptability is crucial in today’s fast-evolving industries. Uta also discusses breaking down silos, navigating uncertainty, and building products with lasting impact, offering invaluable insights for leaders and innovators looking to drive meaningful change.
n this episode of That Pivotal Moment of Change, Kip Voytek shares how his career—starting in political consulting and speechwriting—evolved into game design, UX, data strategy, and digital business transformation, all driven by two essential skills: lifelong learning and curiosity. Kip reflects on the pivotal moments that shaped his journey, from leading roles at cutting-edge agencies and working on iconic accounts like Nike to tackling complex digital strategy challenges with the World Bank. He dives into the power of curiosity, adaptability, and embracing uncertainty, offering insights on navigating career shifts, the evolving role of UX and data in design, and why the most successful people aren’t just experts—they’re expert learners. As Kip puts it, "Whatever success I’ve had has come less from what I know and more about how I’ve managed around what I don’t know." Whether you’re a designer, strategist, or leader navigating change, this episode is packed with valuable lessons to help you stay ahead in an ever-evolving digital landscape.
In this episode of That Pivotal Moment of Change, Sophia Prater, CEO & Founder of Rewired and Chief Evangelist for Object-Oriented UX (OOUX), shares how a pivotal challenge designing CNN’s 2012 election results platform led her to develop a structured approach to UX that simplifies complexity. She discusses the power of self-trust, the importance of seeing the big picture in product design, and why failure is often a hidden opportunity. Sophia also dives into lessons learned from launching a global UX movement, the impact of mentorship and seeking help, and the value of authentic networking in career growth. Plus, she shares her vision for the future of UX in an AI-driven world and offers insights on embracing discomfort, thinking in systems, and designing with clarity.
Register for Sophia's free training at OOUX.com/levelup
Peter Merholz has never followed a conventional path—and that’s exactly what has made him one of the most influential voices in UX and design leadership. In this episode, Peter shares his journey with rare self-awareness, opening up about both the pivotal moments and the missteps that shaped his career.
One of his biggest career shifts came when he realized there was a massive gap in resources for design leaders. That realization led to Org Design for Design Orgs, a book that has since become the go-to guide for structuring and scaling design teams. But the story behind the book is as compelling as the book itself—Peter explains how a job loss turned into an opportunity and how his personal experiences as a design executive shaped the insights within it.
Peter also reflects on the lessons he’s learned about leadership, communication, and how his intense energy and passion—while a strength—sometimes required adjustment in different professional settings. He talks candidly about struggles with job interviews, the challenge of finding a voice in an evolving industry, and how writing has been his most powerful tool for clarity and impact.
Whether you're an early-career designer, a senior executive, or simply fascinated by how careers evolve, this episode is packed with insights on navigating change, embracing personal growth, and shaping the future of design.
In this episode of That Pivotal Moment of Change, Valerie Madden shares her journey as a creative leader in entertainment marketing, from launching iconic TV shows at NBC and Amazon to navigating unexpected career pivots and embracing the transformative power of AI in creative industries. Val opens up about overcoming challenges as a woman, and someone with dyslexia in a traditionally male-dominated industry, highlighting the importance of resilience, adaptability, and authenticity in career growth. She discusses how AI is supercharging creativity rather than replacing it, the evolving role of creatives in an AI-driven world, and how setbacks—like layoffs—can be hidden opportunities for reinvention. Val also shares leadership lessons from her time at NBC’s LGBTQ Employee Resource Group, emphasizing the power of inclusive workplaces where people feel safe to be their authentic selves. Whether you're in marketing, design, or leadership, this episode is packed with insights on embracing change, leveraging technology, and building a career that thrives in uncertainty. Tune in for an inspiring discussion on the future of creativity, innovation, and the human potential behind it all!
In this episode ofThat Pivotal Moment of Change, host Ryan Leffel sits down with Felix Lee, co-founder of ADPList, a platform that has transformed mentorship for professionals across product, engineering, design, marketing, data science, and product research.
Felix shares his journey from being a designer to launching a community-driven company, the key inflection points that shaped ADPList’s rapid growth, and the pivotal moment that forced him to rethink everything. Along the way, he unpacks lessons in leadership, scaling impact, and the key moments that shaped his path.
If you're an entrepreneur, a community builder, or someone navigating career transitions, this episode is for you.
In this episode of That Pivotal Moment of Change, we talk with Teresa Cain—Product & UX Leader and best-selling author of Solving Problems in Two Hours and Next-Gen Product Management. Teresa shares her career journey, from breaking into the product world to leading impactful teams in the tech space. She discusses the power of mentorship, embracing a growth mindset, and staying versatile to overcome challenges like career transitions and the rise of AI in tech. Packed with actionable advice, Teresa also explores how to prioritize innovation, navigate change, and build lasting success in today’s evolving landscape.
In this episode of That Pivotal Moment of Change, we explore the inspiring journey of Connor Joyce—researcher, author of Bridging Intention and Impact, and influencer. Connor shares how he navigated setbacks, embraced change, and discovered his North Star. He discusses the "Four Idols" framework (money, power, pleasure, fame), which has shaped his career perspective, and emphasizes the importance of a growth mindset in turning challenges into opportunities. Connor also shares insights on the evolving role of user research and the influence of AI in the tech landscape. Whether you’re seeking clarity, recovering from a setback, or exploring new opportunities, this episode delivers valuable lessons and actionable advice to help you move forward with purpose.