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In this episode of UX Leadership by Design, host Mark Baldino is joined by three members of Pendo’s design team—Senior Product Design Manager Holly Reynolds, Senior Product Designer John Incampo, and Product Design Intern Ryan Markley—to explore how AI is reshaping real-world design work from the ground up.

They discuss how leadership at Pendo has created a culture of experimentation and empowerment, how AI tools like Bolt, Cursor, and Claude are integrated across the product and design process, and what it takes to balance speed with quality. Whether you're a new designer, an experienced leader, or somewhere in between, this episode is full of honest takes, practical tips, and forward-thinking insights into what AI actually looks like in a modern design team.

Key Takeaways:
1. Culture of Empowerment: Pendo’s leadership doesn’t just allow AI exploration—they encourage it, creating space for experimentation, risk-taking (without risking users), and team-driven innovation.

2. Hands-On AI Tools & Integration: From interns to senior designers, team members are actively using tools like Cursor, Claude, Bolt, and Figma’s AI features to accelerate research, prototyping, documentation, and collaboration.

3. Collaborative Learning Environment: Weekly product + AI sessions and open Slack channels create a culture of shared discovery where everyone contributes wins, tools, and ideas.

4. Practical Guardrails: While AI is everywhere, the team reinforces foundational UX process—reminding each other not to skip steps, misread data, or forget critical thinking in the rush to ship.

5. Real Wins in the Workflow: AI is unlocking richer prototyping, better animation handoff, faster research synthesis, and scalable documentation through tools like custom GPTs.

6. Design Ops Meets AI: The team is rethinking design systems and documentation with AI—exploring ways to automate OOUX structures, update components, and turn dead docs into dynamic tools.

7. Advice for AI Newcomers: Whether you’re overwhelmed, underexposed, or unsure where to start, the team shares practical tips for getting started, experimenting safely, and staying ahead of the curve.

Chapters
00:00 – Welcome + Meet the Pendo Design Trio
01:00 – Career Paths and AI Exposure
05:30 – How Pendo’s Leadership Encourages AI Exploration
08:00 – Internal AI Forums, Slack Channels, and Culture of Sharing
10:50 – Guardrails, Trust, and Responsible Use
13:00 – Balancing Speed with UX Process
15:30 – Cost, Tool Chaos, and What’s Next
17:20 – When AI Skips the Process (and How to Handle It)
20:00 – AI in Design Education: A Student’s POV
25:10 – Real Wins: Richer Prototypes and Faster Handoffs
27:50 – Using AI for Hiring, Microcopy, and Design Systems
33:00 – Turning Design System Docs into Chatbots
36:00 – Advice for Hesitant Designers and AI Newbies
42:30 – Wrap-up + Final Thoughts

Links:

• Connect with Holly on LinkedIn
• Connect with Ryan on LinkedIn
• Connect with John on LinkedIn

• Connect with Mark on LinkedIn
• Fuzzy Math - B2B & Enterprise UX Design Consultancy

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In this episode of UX Leadership by Design, Mark Baldino is joined by veteran UX strategist Paul Boag to explore what’s holding design organizations back—and how to fix it. With over 30 years of experience across sectors, Paul shares why small, underfunded UX teams must stop trying to “own” design and instead empower others through training, standards, and strategic leadership. From breaking down the four pillars of a strong UX practice to candid takes on titles, culture change, stakeholder influence, and democratizing design, this conversation is packed with perspective and practical advice.

Key Takeaways

• Design isn’t yours to own: UX teams need to stop trying to control everything and instead focus on enabling others across the organization to improve user experience.
• Democratizing UX scales your impact: A Center of Excellence (CoE) model empowers non-designers to participate in UX while design leaders maintain standards and guidance.
• Perfection is the enemy of progress: You can’t scale UX by insisting on pixel-perfect quality. Impact at scale comes from breadth, not control.
• Influence comes from empathy: We do user research for customers, but not for stakeholders. Understand your colleagues like users to gain traction.
• Start with working policies: You may not be able to enforce org-wide UX standards—but you can set boundaries for how you work effectively.
• Design leaders must become culture hackers: Changing design maturity in an organization means shifting how teams think, work, and value UX over time.

Chapters

• 00:00 – Introductions and background
• 05:45 – Designer Is the Problem Word
• 08:36 – UX Teams Are Too Small to Own Everything
• 10:58 – Democratizing UX at Oxford
• 13:09 – Letting Go of Pixel Perfection
• 17:02 – 4 Pillars of UX Leadership
• 23:51 – From Working Policies to Org-wide Standards
• 26:57 – Tailor UX Messaging to Stakeholders
• 29:49 – Culture Hacking Through UX
• 32:26 – Resources & Where to Find Paul

Resources & Links

• Connect with Paul Boag on LinkedIn
• Paul’s Website
• Paul’s Awesome Podcast (Latest episode covers his Oxford University case study)

• Connect with Mark on LinkedIn
• Fuzzy Math - B2B & Enterprise UX Design Consultancy

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In this joyful and energizing episode of UX Leadership by Design, Mark Baldino is joined by creativity catalyst Melissa Dinwiddie — a Juilliard-trained dancer turned artist, jazz singer, improviser, and innovation strategist and coach. Melissa helps individuals and teams get unstuck and unlock their creative potential, even (and especially) when they don’t see themselves as creative. She walks us through her deceptively simple “Create the Impossible” framework—Play Hard, Make Crap, Learn Fast—and dives deep into why perfectionism is the enemy of progress.

Whether you’re a self-identified “non-creative,” an overthinking perfectionist, an analytically minded problem-solver, or a leader trying to build more innovative teams, this episode is packed with insight, laughter, and incredibly actionable advice. Bonus content: Melissa was kind enough to create an IMPACT Innovation Checklist for all of our listeners.

Key Takeaways

• Play Hard, Make Crap, Learn Fast – Melissa’s 3-part framework helps people move through creative blocks with intention and joy.
• Everyone is Creative – The belief that creativity is for “others” is one of the biggest blockers to innovation.
• Perfectionism Kills Progress – Creatives often get stuck chasing an unattainable ideal. Melissa advocates for “intentional imperfectionism.”
• Improv Builds Better Teams – Activities like “Time Traveler” help teams build empathy, communicate better, and influence with impact.
• Self-Compassion Fuels Innovation – Letting go of judgment and leaning into curiosity enables us to grow, create, and experiment more freely.

Chapters

• 00:00 – Welcome & Guest Intro
• 00:22 – From Juilliard to Jazz
• 02:24 – The Creativity Myth
• 05:40 – The “Create the Impossible” Framework
• 07:02 – Breaking the “I’m Not Creative” Label
• 11:41 – Improv for Innovation & Communication
• 18:16 – Play Hard, Make Crap, Learn Fast
• 24:03 – Helping Creatives Let Go of Perfectionism
• 27:52 – Mark’s Tile Confession
• 32:40 – Where to Find Melissa & Listener Resources

Resources & Links

• Connect with Melissa Dinwiddle on LinkedIn
• Melissa’s Website and YouTube Channel
• Thank you gift: IMPACT Innovation Checklist

• Connect with Mark on LinkedIn
• Fuzzy Math - B2B & Enterprise UX Design Consultancy

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What’s it really like inside a UX consultancy? In this special in-house episode of UX Leadership by Design, Mark Baldino sits down with two incredible Fuzzy Math teammates — Senior Designer Madeleine Byrne and Senior Project Manager Jaléssa Savage — to talk about what UX leadership looks like from the inside out.

They unpack how projects are structured, how cross-functional teams communicate, and how empathy, clarity, and constraints shape successful outcomes. From wrangling stakeholders to making smart design trade-offs, it’s a behind-the-scenes look at how Fuzzy Math keeps projects human, impactful, and on track — with a few hot takes and laughs along the way.

Whether you’re growing into leadership or just curious how collaborative teams actually work, this one’s packed with insights and energy.

Key Takeaways:

• Balancing Empathy Across Users and Clients – True design leadership means understanding not just end-users but also the internal and external stakeholders shaping the work.
• Why Design Needs Guardrails – PMs aren’t just managing scope — they’re helping passionate designers stay focused and productive within real-world constraints.
• Visuals Are Alignment Tools, Not Just Outputs – Design artifacts aren’t just deliverables; they’re powerful tools for clarifying thinking and aligning teams.
• Stakeholder Trust Starts Early – Trust-building begins with structured project kickoffs and intentional communication — not just when the work hits Figma.
• Client Assumptions Need Evidence – Teams often bring mental models of what they want; our job is to validate, challenge, and guide them with research and strategy.

Chapters:

• 00:00 – Introducing the Fuzzy Math Team
• 00:51 – Madeleine’s Journey from Theater to UX
• 03:19 – Jaléssa’s Journey from Events to Project Management
• 05:57 – Listening and Building Trust with Clients
• 12:47 – How Fuzzy Math Project Teams Work Together
• 25:10 – Common Design Challenges and How We Handle Them
• 31:31 – Working with Clients Who Have a Mental Model
• 43:06 – Hot Takes and Advice for Aspiring Leaders

Links:

• Connect with Madeleine on LinkedIn: https://www.linkedin.com/in/madeleine-byrne-150a959a/
• Connect with Jaléssa on LinkedIn:  https://www.linkedin.com/in/jalessasavage/

• Connect with Mark on LinkedIn
• Fuzzy Math - B2B & Enterprise UX Design Consultancy

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In this episode of UX Leadership by Design, Mark Baldino talks with Chris Silvestri, founder and chief conversion copywriter at Conversion Alchemy. Chris brings a rare blend of backgrounds—software engineer, UX designer, and conversion copywriter—to tackle one of the toughest challenges in B2B: turning complex decision-making into clear, effective messaging. We dig into his AI-powered empathy framework, PATH, and explore how he uses customer research, simulated personas, and real language to help teams write content that connects. For anyone working in UX, product, or content, this is a masterclass in aligning messaging with how humans actually think, feel, and decide.

Key Takeaways

• Empathy can be “engineered” – Chris shares his AI-powered PATH framework (Prepare, Articulate, Test, Harmonize) to simulate customer personas and deepen user empathy.
• Conversion is a series of micro-decisions – It’s not just about a final click—every piece of copy should guide users through their decision-making process one step at a time.
• Vague messaging creates drop-off – If users can’t understand what you do, who it’s for, or why it’s different in a few seconds, they’ll bounce.
• Expectation-setting is everything – From homepage copy to “Book a Demo” CTAs, clear expectations can dramatically reduce friction and build trust.
• AI won’t replace writers—it augments them – Used correctly, LLMs can simulate customers, test ideas, and accelerate iteration—if humans remain in the loop.
• UX, sales, and copy need a shared foundation – Chris’s work helps unify these functions by anchoring messaging in customer research and decision psychology.

Chapters

• 00:00 – From Engineering to Empathy
• 03:47 – Lessons from Dangerous Machines
• 06:02 – The Pyramid of Conversion
• 10:56 – Jobs to Be Done in B2B
• 13:47 – Selling to the Whole Buying Team
• 17:45 – Common Copy Mistakes
• 25:45 – AI and Empathy: The PATH Framework
• 31:00 – How Chris Uses AI Personas for Better Copy
• 33:51 – AI as an Accelerator, Not a Replacement
• 34:00 – From Copywriter to Conversion Architect

Resources & Links

• Conversion Alchemy Website, Newsletter, & Podcast
• Connect with Christopher Silvestri

• Connect with Mark on LinkedIn
• Fuzzy Math - B2B & Enterprise UX Design Consultancy

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In this episode of UX Leadership by Design, Mark Baldino talks with Mauricio Steffen, Senior Director of Product Management at Ericsson, about the crucial role customer research and empathy play in successful product management. Mauricio shares his unique career path, transitioning from corrections officer to frontline support, then into product management, highlighting how deep, empathetic listening skills have been essential across all roles. The conversation explores how to scale customer feedback processes, synthesize insights effectively, and navigate stakeholder management. Mark and Mauricio challenge the common misinterpretation of Henry Ford’s quote about customer research, emphasizing the importance of genuinely understanding underlying customer needs. Practical advice is offered for breaking through organizational blinders, advocating for meaningful change, and maintaining balance when strategic initiatives seem misaligned with immediate customer requests.

Key Takeaways

• Empathy and Active Listening: Genuine empathy and active listening are key skills that transcend industry and job function, essential for product management success.
• Scaling Customer Feedback: Utilize scalable methods like AI (LLMs) to analyze and summarize customer feedback at scale, uncovering patterns and root causes effectively.
• Root Cause Analysis: Go beyond surface-level customer requests by digging deeper to uncover true underlying problems and needs, rather than just stated wants.
• Stakeholder Engagement: Engage stakeholders early, make them feel heard, and clearly communicate decisions to achieve alignment and minimize resistance.
• Embracing Customer Feedback: Treat customer feedback as a valuable gift; show appreciation and continuously demonstrate that input shapes your product decisions.
• Admitting Mistakes: Develop the courage to pivot or stop projects when customer and market feedback indicates potential failure; maintaining an honest, reflective process is key to sustainable success.

Chapters

• 00:00 Introduction to Mauricio Steffen
• 02:09 Career Journey: From Corrections Officer to Product Management
• 06:57 The Role and Philosophy of Product Management
• 09:59 Influencing Stakeholders: Education, Listening, and Empathy
• 12:42 Scaling Customer Feedback and Leveraging AI
• 15:34 Why “Faster Horse” Is a Cop-Out: Understanding Customer Needs
• 22:49 Breaking Organizational Blinders with Customer Insights
• 26:07 The Challenge of Admitting Mistakes and Changing Course
• 29:37 Root Cause Analysis: From Wants to True Customer Needs
• 35:33 Empathy as the Key Skill for All Stakeholder Management

Resources & Links

• Connect with Mauricio Steffen on LinkedIn

• Connect with Mark on LinkedIn
• Fuzzy Math - B2B & Enterprise UX Design Consultancy

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In this episode of UX Leadership by Design, Mark Baldino sits down with David Hirschfeld, founder and CEO of Tekyz, about the Launch First methodology—a metrics-driven approach to de-risking product development and achieving product-market fit before building software. David shares insights from working with over 90 startups, highlighting the common pitfalls that lead to failure, particularly the mistake of waiting too long to validate revenue. He breaks down how to identify the right niche, perform root cause analysis, and use high-fidelity prototypes to pre-sell software before investing in an MVP. Whether you're a startup founder, a product leader, or iterating on a new SaaS offering, this episode offers actionable strategies to validate demand, avoid wasted development, and accelerate success.

Key Takeaways

• The Biggest Mistake Startups Make - Most startups fail due to lack of product-market fit, not running out of money. Waiting too long to validate revenue leads to wasted resources and increased risk.
• Flipping the MVP Approach - Instead of using an MVP to test product-market fit, use it to validate product-solution fit—ensuring real customers will use it, not just buy it.
• Pre-Selling Before Building - High-fidelity prototypes that feel like real software can be used to sell the vision and secure early customers before writing a single line of code.
• The Power of Niche Analysis - Startups should identify a niche where pain points have both a high cost and a high perceived impact, ensuring customers are both willing and able to pay.
• The Scientist vs. The Believer - Founders often wear the "black robe" of belief in their vision, but success comes from adopting the "white coat" of data-driven decision-making.
• Speed Matters: Fail Fast, Fail Cheap - Instead of spending years and millions developing a product that may not sell, Launch First helps founders validate demand in 3-5 months.
• Lifetime Licenses Aren’t Crazy - For some SaaS models, offering lifetime licenses in pre-sales can be a smarter way to fund development than raising capital and losing equity.

Chapters

• 00:00 Introduction to David Hirschfeld's Journey
• 03:01 Why Most Startups Fail: The Real Reason
• 09:31 Understanding Product-Market Fit vs. Product-Solution Fit
• 14:46 Sell Before You Build: The Power of Pre-Sales
• 19:31 Finding the Right Niche with Data-Driven Decisions
• 24:31 From Founder to Scientist: The Mindset Shift
• 28:46 Building a Sales Funnel for Early Traction
• 34:11 When to Start Building Your MVP

Resources & Links

• Connect with David Hirschfeld on LinkedIn
• Tekyz

• Connect with Mark on LinkedIn
• Fuzzy Math - B2B & Enterprise UX Design Consultancy

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In this episode of UX Leadership by Design, Mark Baldino sits down with Mike Nowak, Principal Product Manager at Deloitte Digital, to explore the philosophy and pragmatism behind product management. Mike shares his unconventional journey from theology and philosophy to product leadership, emphasizing the importance of humility, adaptability, and cross-functional collaboration in the product space. The conversation dives into the interplay between UX, engineering, and product management, the challenge of defining “what to build and why”, and how organizations can create a culture where mistakes lead to learning, not failure. The discussion also covers why product decisions are often political, the evolving role of product ops, and how businesses can better align incentives to build truly user-centered products.

Key Takeaways

• Product as the Interstitial Role - Product management isn’t just about writing requirements—it’s about bridging the gaps between UX, engineering, and business stakeholders, ensuring alignment on desirability, feasibility, and viability.
• Pragmatism in Product Development - The best teams focus on what works in the real world, not just what sounds good in theory. Product teams must fail fast, test ideas quickly, and iterate based on real user feedback.
• Why Product Decisions Are Political - Prioritization isn’t just about logic—it’s about navigating internal politics, aligning incentives, and helping stakeholders understand why some initiatives move forward while others don’t.
• The Rise of Product Operations - Many organizations struggle with operationalizing best practices. Product Ops can bring structure to decision-making, create data-driven prioritization frameworks, and help teams scale effective processes.
• Psychological Safety Drives Innovation - The most effective teams aren’t afraid to say, “We don’t know yet.” Creating an environment where mistakes are learning opportunities is critical for long-term product success.

Resources & Links

• Connect with Mike Nowak on LinkedIn
• Book: Getting Naked by Patrick
• Book: Product Operations: How successful companies build better products at scale

• Connect with Mark on LinkedIn
• Fuzzy Math - B2B & Enterprise UX Design Consultancy

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In this episode of UX Leadership by Design, Mark Baldino talks with Dave Seligsohn, founder of A2O Consulting, about creating a culture of innovation and driving business growth. Drawing from his rich background in education and leadership, Dave shares insights into the challenges small businesses face, such as breaking revenue ceilings, optimizing operations, and achieving growth. He highlights the importance of fostering innovation through intentional processes, forming dedicated teams, and leveraging data-driven decision-making. The conversation offers practical strategies for establishing an innovation pipeline, validating ideas, and navigating organizational challenges, making it an invaluable guide for leaders and entrepreneurs.

Key Takeaways

• The Cycle of Innovation – Effective innovation is intentional and embedded into company culture, driven by an innovation team tasked with surfacing, testing, and implementing ideas.
• Breaking Revenue Ceilings – Small businesses often face growth plateaus due to overreliance on founders; collaboration, delegation, and external advisors can help overcome these challenges.
• Prevention Over Cure – Leaders should prioritize continuous innovation to avoid desperation-driven solutions during crises.
• Structured Idea Validation – A systematic approach to market validation, involving customer feedback and financial analysis, reduces risk and ensures alignment with business goals.
• Leadership’s Role in Innovation – Leadership should sponsor and support innovation initiatives, but remain hands-off during idea generation to encourage creativity.
• The Power of Data in Decision-Making – Businesses must identify and focus on the most relevant data points to track progress and ensure operational efficiency.
• Overcoming Fear of Change – Allocating budget and fostering openness to new ideas are critical to embracing innovation as a business growth driver.

Resources & Links

• Connect with Dave Seligsohn on LinkedIn

• Connect with Mark on LinkedIn
• Fuzzy Math - B2B & Enterprise UX Design Consultancy

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In this episode of UX Leadership by Design, Mark Baldino sits down with Joe Sticca, a seasoned expert blending technology, digital experiences, and product innovation, to explore the transformative impact of generative AI on product management and design. Joe shares his journey from software development to digital experience leadership, emphasizing the importance of adopting an "editor mindset" to harness AI for efficiency, creativity, and strategic decision-making. The conversation delves into how AI accelerates feedback loops, enhances data analysis, and mitigates risks, empowering teams to deliver richer MVPs and foster better collaboration. Joe also touches on the evolving role of Web3, tokenization, and platforms like Roblox and Decentraland in shaping the future of customer engagement.

KEY TAKEAWAYS

• The "Editor Mindset" for Success - Generative AI empowers professionals to focus less on manual tasks and more on refining and validating creative ideas, improving product value and user outcomes.
• Efficiency Meets Creativity - AI tools enable teams to test, iterate, and mitigate risks faster, allowing for richer MVPs and more impactful user experiences.
• Depersonalizing Decision-Making - Using AI to analyze and act on data removes bias, fosters objectivity, and encourages Socratic discussions for better outcomes.
• Expanding the Idea Set - With time saved through AI, teams can shift their focus to exploring more innovative and valuable ideas that enhance user and business value.
• Shortening Feedback Loops - Real-time data insights powered by AI allow product teams to make faster, more informed decisions without waiting for traditional analytics cycles.
• Adapting Skills for the AI Era - Professionals must develop a nuanced understanding of business value, context, and creative problem-solving to thrive alongside AI tools.

CHAPTERS

• 00:00 Introduction and Background
• 03:09 The Impact of Generative AI on Development
• 06:02 Navigating Trust in AI Tools
• 08:52 The Role of AI in Product Management
• 11:46 The Editor Mindset in Product Development
• 14:47 Future Trends in Product Management and Design
• 17:51 Closing Thoughts and Future Opportunities

LINKS:

• Connect with Joe on LinkedIn: https://www.linkedin.com/in/joesticca/

• Connect with Mark on LinkedIn
• Fuzzy Math - B2B & Enterprise UX Design Consultancy