In this episode of Design Shift, I talk with Gregory Stock—fractional Chief of Staff, design strategist, and executive coach—about what it takes to lead with empathy, taste, and strategic clarity in an age defined by speed and AI.
Gregory shares his journey from the art world to the world of startups, revealing how his early work in museums shaped his approach to systems thinking, storytelling, and design at scale. We dive into his experience with The Bay Lights project in San Francisco, the power of deep listening in client work, and why he believes taste is something you build through time, discomfort, and curiosity.
He also opens up about how the DMBA program helped him close a “big empathy gap,” how he uses AI as a tool for dialogue—not just output—and what advice he has for the next generation of design leaders navigating ambiguity and change.
If you’ve ever wrestled with what it means to be both creative and strategic—or wondered how to stay grounded while working at the edges of art, business, and technology—this episode is for you.
Subscribe to Design Shift for more conversations with designers, founders, and creative leaders shaping what’s next.
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In this episode of Design Shift, Justin Lokitz sits down with Chris Basey, founder and CEO of Comedia, a boutique design agency that’s quietly outpacing the Big Four. From building real products for Google, BMW, and Atlassian to using AI as a “force multiplier,” Chris shares how small design teams are scaling impact without scaling headcount.
They dive into:
How boutique agencies win by making, not pitching
Why design thinking needs a reset (but not a funeral)
What AI can (and can’t) do for product designers
How to avoid “vibe coding” and stay relevant in an AI-driven world
The future of boutique consulting—and why the full-service agency model is dying
Whether you’re a design leader, founder, or creative strategist, this episode is packed with honest insights, hard-earned lessons, and practical advice to help you thrive in a shifting industry.
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#DesignConsulting #AIinDesign #BoutiqueAgencies #UXLeadership #ProductDesign #DesignThinking #CreativeStrategy #Comedia #ChrisBasey #DesignShift #InnovationConsulting #DesignLeadership
Get ready to level up your design game. In this episode of Design Shift, veteran UX strategist Nick Cawthon (founder of Gauge and professor of Data Literacy at CCA) breaks down how to stay indispensable when AI can generate a wireframe in seconds. We cover why direction beats deliverables, how to anchor machine learning in human insight, and what happens when design and engineering finally merge.
🔑 What you’ll learn
The new definition of design in an AI-saturated world
A step-by-step playbook for scaling research with 40 M data points—without losing empathy
How “prompt-engineered” Design Ops collapses hand-offs and saves dev cycles
Nick’s 3-year learning plan for future-proof careers
⏱ Key insights…
0:00 Opener1:08 Meet Nick Cawthon – 25-year UX veteran2:38 AltaVista to Gauge: forging a data-driven career10:43 Design is direction, not deliverables14:58 UI vs UX vs Usability: emotion over pixels16:11 Uber’s “moving cars” trick for micro-delight21:08 40 M Airbnb reviews: AI starts with qual hypotheses22:38 Why Double-Diamond skills still matter35:07 Hybrid “diamond-shaped” orgs win36:08 Design Ops becomes prompt-engineering44:03 “Figma isn’t the web” – prototype in live code46:08 Near-production hand-offs & component libraries56:58 Nick’s 3-year learning plan59:53 Take the free AI-readiness assessment at retrain.gauge.io
🔗 Resources• Gauge: https://gauge.io• AI-Readiness Self-Assessment: https://retrain.gauge.io
👉 Subscribe for weekly deep dives on design leadership, innovation, and the future of work. Smash that 👍 if you find value, and drop your questions for Nick in the comments—we might answer them in the next episode!
#UXDesign #AI #DesignLeadership #ProductDesign #NickCawthon #Gauge #GenerativeAI #DesignOps
What happens when a top UX leader leaves big tech and builds something of her own? In this episode, Maya Elise Joseph-Goteiner—former Google researcher and founder of Velocity Ave—shares her powerful journey from the inside of Area 120 to launching a nimble, high-impact agency.
We talk about the identity crisis that comes with leaving a well-known role, the freedom (and fear) of starting from scratch, and how designers can lead by embracing ambiguity—not avoiding it. Maya also unpacks her view of design as a systems-level negotiation between business, tech, and humanity—and why that matters more than ever in the age of AI.
If you’re a designer, strategist, or creative leader wondering what’s next—this one’s for you.
🎙️ From Designer to Founder: James Song on Leadership, Intent & Building What Matters
In this episode of Design Shift, we sit down with James Song—a renowned design leader who has shaped products and teams at companies like Meta, Uber, Tinder, and Frog—to explore the real journey from designer to founder.
Whether you’re a product designer, creative lead, or aspiring entrepreneur, James breaks down what it really means to lead:
→ Why leadership starts with curiosity, not titles
→ How design becomes a strategic force inside organizations
→ Why founding a company is an act of service and systems thinking
→ Tools, mindsets, and advice for designers ready to build something of their own
🧠 TOPICS COVERED:
00:03:08 Toy Story and the Pixar Moment That Sparked a Career
00:04:00 Typography, Layout, and the Shift from Animation to Design
00:06:16 Defining Design as “Intent Made Real”
00:06:24 Shifting from Execution to Vision
00:06:58 Leadership Emerges from Curiosity, Not Titles
00:14:06 Learning from Frog, Apple, and the Origins of Design Language
00:15:27 Influence vs. Authority: The Real Leadership Challenge
00:15:48 Advice to Designer-Founders: Learn Tools and Build Systems
00:20:16 Coaching Emerging Leaders Through Real Strategic Work
00:23:31 Leading Without a Title: Systems Thinking and Ownership
00:27:44 From Design Leader to Founder: Making the Leap with Intent
00:30:58 Building Your First Company: Product, Team, and Execution
00:35:20 Lessons from Hypergrowth at Uber and Scale at Meta
00:38:12 Seeing the Full Business Landscape as a Designer
00:41:02 Balancing Craft and Strategy as a Founder-Leader
00:44:17 Designing Tools, Culture, and Systems with Intent
00:46:25 Making Design Decisions that Reflect Your Values
00:48:39 Encouragement to Designers: You Already Have What It Takes
00:50:22 James’s Final Advice to Aspiring Designer-Founders
🔔 Subscribe for more conversations with design leaders, founders, and creative pioneers: @DesignShift
👇 Drop a comment if this inspired you—and don’t forget to like + share it with a designer who needs to hear this!
🔥 WHO SHOULD LISTEN TO THIS:
Designers transitioning into leadership
Creatives thinking about starting their own company
Product thinkers interested in design-led strategy
Founders who care about craft, culture, and intent
📩 Want more insight like this? Subscribe to the Design Shift Newsletter: https://www.designshift.me/
#DesignLeadership #DesignerFounder #CreativeLeadership #UXDesign #StartupJourney #ProductDesign #Founders #DesignThinking #LeadershipTips #DesignShiftPodcast
How Design Can Drive Climate Action | The Design Shift Podcast with Marc O'Brien
In this episode of The Design Shift Podcast, host Justin Lokitz sits down with Marc O'Brien, an award-winning creative strategist, designer, and educator dedicated to leveraging design for climate action. They discuss the role of design in amplifying existing climate solutions, the significance of teaching climate design, and how Marc's initiatives, like Climate Designers and his work with studio heads, are reshaping the industry for a sustainable future.
Don't miss this deep dive into the intersection of design and sustainability!
In this episode of Design Shift, we sit down with design and innovation leaders Elizabeth Glenewinkel and Mario Ruiz to explore how AI and the Jobs to Be Done (JTBD) framework are transforming the role of designers. Learn how they’re helping teams move from tactical execution to strategic leadership by combining human-centered design, critical thinking, and agentic workflows. We dive into their journey at Salesforce, the evolution of innovation teams, and how designers can adapt, lead, and thrive in an AI-first world.Whether you’re a product designer, design strategist, or innovation leader, this conversation is packed with actionable insights on staying relevant and making meaningful impact in a rapidly changing landscape.
This is the Design Shift podcast, your weekly guide to mastering the leap from creative expert to confident design leader—packed with actionable insights, proven strategies, and real-world wisdom. In this episode, I chatted with Kevin Flores, a double-threat product and design leader, about everything from the value of design, blurring the boundaries of product and design, and even AI. Kevin recently co-authored the "Design Career Handbook" with his wife, Jeanine Flores, who is also a longtime design leader…which is indispensable for any early to mid-career designer or creative. Keep listening to learn where your big breaks will probably come from, and remember to subscribe to the show and the Design Shift newsletter if you enjoy the episode.
