Confidence, Bias, and Opportunity: Lessons from Women Leaders in Tech Building the Future of AI and Work (International Women’s Day Special Episode)

Send a textAdrian McDermott is Chief Technology Officer at Zendesk, where he leads the company’s product management and engineering teams and helps shape the technology behind one of the world’s most widely used customer service platforms. He joined Zendesk in 2010 and has played a key role in guiding the company’s product and platform strategy as customer experience continues to evolve in the age of AI. Drawing on years of experience building enterprise software used by service teams around the world, Adrian brings a thoughtful perspective on how AI can help organizations deliver better customer service while allowing people to focus on the work humans do best.In this conversation, we discuss:How customer service evolved from a cost center with rigid scripts and binders into a strategic function where technology helps teams deliver better experiences.Why customer service leaders shouldn't fear automation — and why everyone has a "service debt" that AI can finally help pay down.The shift from traditional contact centers to AI-enabled service platforms that help companies respond faster while improving both employee and customer experience.Lessons Adrian learned scaling Zendesk from a small product team to a global platform serving 100,000 customers and how product-led growth shaped that journey.The critical challenge of moving from non-deterministic, creative AI models to deterministic, reliable solutions necessary for enterprise trust and safetyThe future of context engineering and why the next major leap in AI won't be about superintelligence, but about building systems that capture and act on the knowledge created in every customer interaction.Resources:Subscribe to the AI & The Future of Work NewsletterConnect with Adrian on LinkedInAI fun fact articleOn How the impact of the pandemic on leaders, culture, and the evolving nature of work

Send a textTo celebrate International Women’s Day, this special compilation episode of AI and the Future of Work revisits powerful moments from past conversations with women leaders shaping technology, artificial intelligence, and the future of work.Across industries and roles, these leaders share reflections on career growth, leadership, resilience, and the barriers women still face in technology and executive leadership. Their stories reveal how confidence, mentorship, and opportunity shape who gets to lead in emerging industries like AI.As artificial intelligence reshapes how organizations operate and how work evolves, representation in the people building and guiding these technologies matters more than ever. Expanding access and opportunity is essential to creating a more innovative and inclusive future of work.Featured GuestsCharlene Li – Author, Keynote Speaker & Strategic Advisor. Listen to the full conversation here: [https://www.buzzsprout.com/520474/episodes/3970637]Daphne Jones – CEO at The Board Curators. Listen to the full conversation here: [https://www.buzzsprout.com/520474/episodes/12105172]Patty Hatter – President & COO at Opsera. Listen to the full conversation here: [https://www.buzzsprout.com/520474/episodes/5939122]Mona Sabet – SVP at GCG. Listen to the full conversation here: [https://www.buzzsprout.com/520474/episodes/16747398]Tess Posner – CEO and Founder at AI4ALL. Listen to the full conversation here: [2019: https://www.buzzsprout.com/520474/episodes/2207636 - 2025: https://www.buzzsprout.com/520474/episodes/17326118] What You’ll LearnWhy women often wait until they feel fully qualified before pursuing leadership rolesHow imposter syndrome shapes career decisions and confidence in techWhy perfectionism can limit growth for technical leadersHow hiring practices based on brand signals reinforce gender imbalanceWhy diversity in AI development leads to better technology outcomesHow leaders can expand opportunity for the next generation of women in tech💬 Inspired by something you heard in this episode?Share your favorite insight about leadership, risk-taking, or expanding opportunity for women in AI and tech, and tag us on social.And don’t forget to subscribe to AI and the Future of Work for more conversations with the leaders shaping the future of work.

Send us Fan MailMatt Britton is Founder and CEO of Suzy and a leading voice on how AI and generational change are reshaping business. He is the author of the best-selling book Generation AI: Why Generation Alpha & The Age of AI Will Change Everything, and has advised more than half of the Fortune 500 on marketing, innovation, and consumer behavior. Drawing on decades of experience working with global brands, Matt examines why AI is shifting the economy from knowledge tasks to creative problem solving, why reskilling will define the next decade, and how leaders can build organizations that elevate human judgment in an AI-driven world.In this conversation, we discuss:Why AI is accelerating a shift from memorization and knowledge tasks toward creativity, critical thinking, and real problem solving.Why reskilling, not upskilling, will define the next decade and why that transition will be harder than most leaders admit.How Gen Alpha, the first AI-native generation, will reshape expectations around work, brands, privacy, and employer relationships.Why robotics will transform the service economy sooner than most leaders expect, and what that means for jobs.The mistake companies make when they chase AI tools instead of focusing on the most important problems to solve.How hyper-personalization and an “audience of one” are redefining trust, value creation, and meritocracy in business.Resources:Subscribe to the AI & The Future of Work NewsletterConnect with Matt on LinkedInAI fun fact articleOn How Kai Nunez, Vice President of Research & Insights at Salesforce, is making tech teams take ownership of AI ethics

Send us Fan MailKourtney Cross is a RiseUp with ServiceNow Graduate and Business Analyst at Leidos. With a background in accounting and operations, Kourtney saw a shift happening in the enterprise tech landscape and decided he wouldn't be left behind. He immersed himself in a new ecosystem, earned multiple certifications through the RiseUp program, and built his own hands-on projects to prove his skills to skeptics.But his story isn't just about learning new software. It's about the grit it takes to pivot your career in public. Kourtney joins Dan Turchin to share what it really looks like to go from "credentials on paper" to delivering value in the AI economy, and why he believes compounded effort always yields success.In this conversation, they discuss:Why Kourtney saw a market shift and decided to dive in headfirst, and how that decision became a pivotal career inflection point.How RiseUp with ServiceNow program enables ambitious early-career professionals to obtain certifications, build real skills, and pivot into future-proof tech roles.What certifications actually do, and don’t do, in the job market, and how Kourtney differentiated himself by building and showcasing a hands-on project.How to proactively leverage AI as a business analyst, from writing user stories to tightening requirements, instead of fearing job displacement.Where AI should accelerate productivity and where clear human boundaries still matter, especially in high-stakes areas like healthcare and admissions decisions.Why patience, resilience, and what Kourtney calls “compounded effort” matter more than credentials alone when breaking into tech and building long-term career momentum.Resources:Subscribe to the AI & The Future of Work NewsletterAI @ Work – Level One Leaders certificationConnect with Kourtney on LinkedInAI fun fact articleOn how AI can unleash human potentialExplore more about RiseUp with ServiceNow

Send us Fan MailScott Strickland is Chief Commercial Officer at Wyndham Hotels & Resorts and former Chief Information Officer of Wyndham Hotel Group, where he led technology and AI initiatives across one of the world’s largest hospitality portfolios. With experience spanning global operations, enterprise data strategy, and board-level leadership, he has built a reputation for translating business priorities into scalable technology execution.Drawing on that experience, Scott brings a pragmatic lens to how organizations align AI with business strategy, prioritize initiatives by ROI and time to value, and scale responsibly while building trust across teams.In this conversation, we discuss:How Scott translates business needs into technical AI execution while keeping a sharp focus on measurable dollar impact.Why winning board support for AI requires the “4 E’s” framework, and how making AI a recurring agenda item changes the trajectory of investment.How to scale from four initial AI use cases to more than 340 by prioritizing ROI, time to value, and data readiness.Why AI works best as a co-pilot that removes friction and drudgery, rather than as a replacement for frontline teams.What it takes to build trust with employees during AI transformation, including transparency, reskilling pathways, and new roles like AI coaches.Why security, privacy, and risk management must be built into AI initiatives from day one, and how servant leadership creates the cultural foundation for responsible adoption.Resources:Subscribe to the AI & The Future of Work NewsletterConnect with Scott on LinkedInAI fun fact articleOn how the journey from intern to a $5B unicorn happens

Send us Fan MailIn this special February compilation episode of AI and the Future of Work, we explore what it truly takes to build AI companies designed to last.While AI innovation moves fast, enduring companies are built on fundamentals. Clear problem selection. Thoughtful product design. Ethical intent. Leadership under uncertainty. And the resilience required to keep going when the market pushes back.This episode brings together insights from founders and operators who have built, scaled, and sustained AI-driven companies across different stages and industries. Their stories reveal a shared truth. Long-term success depends less on hype and more on discipline, courage, and trust.Featured GuestsEric Olson, CEO and Co-founder of Consensus - Listen to the full conversation here: https://www.buzzsprout.com/520474/episodes/11574063 Rich White, Founder of UserVoice and CEO of Fathom - Listen to the full conversation here: https://www.buzzsprout.com/520474/episodes/11911533 Dmitry Shapiro, CEO of MindStudio - Listen to the full conversation here: https://www.buzzsprout.com/520474/episodes/14866979 Daniel Marcous, Founder and CTO of April, former CTO of Waze - Listen to the full conversation here: https://www.buzzsprout.com/520474/episodes/12679210 George Sivulka, CEO of Hebbia - Listen to the full conversation here: https://www.buzzsprout.com/520474/episodes/16572788 What You’ll LearnWhy founders must act before certainty appearsHow solving real pain leads to stronger, longer-lasting companiesWhat ethical intent looks like in practical AI system designWhy trust, accuracy, and discipline matter more than speedHow resilience shapes leadership through uncertaintyWhat separates durable AI companies from short-lived experimentsInspired by something you heard in this episode?Share your favorite insight on social and tag us. We’d love to hear what resonated with you. And don’t forget to subscribe to AI and the Future of Work for more conversations with the founders and leaders shaping what comes next.Other special episodes: Lessons from Four Unicorn CEOs Disrupting Massive Markets with AI (Special Episode)Artificial General Intelligence: Can Machines Really Think Like Us? (Special Episode)Ethical AI in Hiring: How to Stay Compliant While Building a Fairer Future of Work (HR Day Special Episode)AI and the Law: How AI Will Change Legal Careers (Special Episode)AI and Safety: How Responsible Tech Leaders Build Trustworthy Systems (National Safety Month Special)Lessons from Leaders: How AI Is Redefining Work and the Human Experience (Labor Day Special Episode)365: What We’ve Learned from 364 Expert Conversations (Special Episode)

Send us Fan MailAndrea Iorio is one of Brazil’s most requested keynote speakers on digital transformation, innovation, and leadership. His work has reached more than 50,000 people through live talks, and his podcasts have surpassed 300,000 downloads. A former Head of Tinder across Latin America and Chief Digital Officer at L’Oréal Brazil, he brings firsthand experience leading digital change inside large organizations. Today, he advises leaders, teaches MBAs, and studies how AI reshapes work, skills, and decision making. His latest book, Between You and AI, explores how humans stay relevant as machines take on more cognitive tasks.In this conversation, we discuss:Why AI replaces tasks rather than entire jobs, and how reframing work around tasks changes how leaders redesign roles, workflows, and value creation.Andrea shares surprising data from a global HR survey that reveals why 93% of HR leaders prioritize soft skills over hard skills in new hires, and why this trend signals a massive shift in the future of work.Andrea outlines nine new skills, grouped into Three Pillars of Transformation essential for professionals and leaders: cognitive, behavioral, and emotional.Why asking better questions matters more than producing answers, and how prompting extends beyond AI inputs into everyday leadership and decision making.Andrea shares how L’Oréal’s reverse mentoring program shifted the C-Suite’s perspective on emerging digital trends, demonstrating why understanding the Gen Z consumer requires direct immersion over passive presentations.What the rise of autonomous AI agents means for responsibility, goal setting, and collaboration, and why agency remains a human obligation even as systems gain autonomy.Resources:Subscribe to the AI & The Future of Work NewsletterConnect with Andrea on LinkedInAI fun fact articleOn how investors decide what to fund in gen AI and what most entrepreneurs get wrong

Send us Fan MailLynne Chou O’Keefe is the Founder and Managing Partner of Define Ventures, one of the largest early-stage health tech investment firms, with $800 million in assets under management.With deep experience across digital health, venture capital, and frontline healthcare systems, Lynne brings a clear-eyed view of why the industry is changing now and where AI can make a meaningful difference. She is widely recognized for her work backing companies that rethink access, outcomes, and patient experience, and is a trusted voice on how technology, ethics, and human judgment must come together to move healthcare forward.In this conversation, we discuss:Why healthcare still runs on fragmented systems and what that means for where AI can truly move the needle.How the shift from fee-for-service to value-based care changes incentives and pushes the system toward prevention over volume.Why patients now expect healthcare to work like transportation or food delivery, and how that expectation reshapes care delivery.The three phases of AI in healthcare, from administrative efficiency to clinical workflow support and, eventually, clinical decision-making.Where the ethical boundary sits today between AI-assisted care and AI-led decisions, especially when access to care is limited.Why the future of healthcare is hybrid by design, with AI augmenting clinicians rather than replacing human judgment.Resources:Subscribe to the AI & The Future of Work NewsletterConnect with Lynn on LinkedInAI fun fact articleOn how AI is fixing the biggest problem faced by doctors.

Send us Fan MailDave Kellogg is a leading voice in enterprise software, SaaS metrics and go-to-market strategy. A four-time guest on AI and the Future of Work, Dave brings decades of hands-on experience inside SaaS companies to challenge how leaders think about growth, metrics, and execution. He is an Executive-in-Residence at Balderton Capital and the author of Kellblog. His perspective is shaped by years spent leading and advising software businesses from early stages through scale.In this conversation, we discuss:Why Dave argues that we are increasingly working for the algorithm, not the other way around, and how that shift shows up in SEO, productivity, and workplace behavior.Why SaaS is not dying but is under real pressure, and how claims that companies can easily replace systems like Salesforce or Workday misunderstand how enterprise software actually works.How AI changes jobs by pushing work up the value chain rather than simply eliminating roles, and why history suggests societies adapt faster than we expect.Why trust becomes more valuable as AI floods the world with low-quality content, and how brands, creators, and leaders must earn credibility in an era of front-run information.What the move from the Rule of 40 to the Rule of 60 signals about today’s market, and why many mid-scale SaaS companies now face uncomfortable strategic choices.How venture capital is becoming more financialized, what that means for founders, and why AI may accelerate the shift toward larger funds, bigger bets, and fewer safety nets.Episode Chapters00:00 Why Dave Kellogg’s Annual SaaS Predictions Matter More Every Year03:53 Working for the Algorithm, Not the Other Way Around06:10 “Death of SaaS”: Why Enterprise Software Isn’t Going Away08:56 Why Enterprise Software Is Built to Last11:51 AI and Jobs: Why Work Disappears Differently Than We Expect16:31 The New Jobs AI Creates and Why Humans Stay Essential at Work19:22 Why Trust Becomes the Most Valuable Currency in an AI-Driven World24:23 Why AI Forces Us to Rethink Trust, Media, and Credibility27:57 Why the Rule of 60 Is Replacing the Rule of 40 for Startups in 202633:44 How Venture Capital Is Becoming a Financial Services Business41:47 Why Silicon Valley’s New Willingness to Take Political Positions Surprised Many Founders45:57 What the Grateful Dead Can Teach Us About Business, Creativity, and LegacyResources:Subscribe to the AI & The Future of Work NewsletterConnect with Dave Kellogg on LinkedInKellblog Predictions for 2026AI fun fact articleOn How AI is Making Networks SmartPrevious episodes in AI & The Future of Work featuring Dave:[2025] 324: 2025 predictions with Dave Kellogg: The Future of AI, SaaS, and Business[2024] Dave Kellogg, SaaS whisperer and EIR at Balderton Capital, predicts the future of AI, Silicon Valley, and venture capital[2023] Special episode: Dave Kellogg, serial CEO, investor, and SaaS pioneer, shares his (provocative) tech predictions for 2023

Send us Fan MailLynn Thoman is a professor at Columbia University’s School of International and Public Affairs and the founder of 3 Takeaways, a top 1% global podcast known for distilling big ideas from influential leaders shaping policy, business, and society. Drawing on experience across corporate strategy, public sector advisory work, and board service at institutions such as the Brookings Institution and Harvard’s Kennedy School of Government, Lynn brings a cross-sector lens to how AI is reshaping decision-making, learning, and human potential.In this conversation, we discuss:Why AI is best understood as an amplifier of human capability, especially in leadership, where judgment and choices matter more than technology.How the real upside of AI is giving people more space for imagination, empathy, and meaningful human connection.How to prepare students and professionals for an AI-shaped job market by prioritizing learning paths, adaptability, and relationships over fixed career tracks.Why the biggest risks of AI come from small, hard-to-detect changes in data or models that can create serious downstream harm.How AI is pushing education, work, and leadership back toward core human skills like judgment, curiosity, and imagination.Where cautious optimism comes from, including AI’s potential to expand access to knowledge, healthcare, and opportunity when used with care.Resources:Subscribe to the AI & The Future of Work NewsletterConnect with Lynn on LinkedInAI fun fact articleOn How genAI studios launch AI-first companiesOther podcast episodes mentioned on the show:On reinventing the academic curriculum for MBAs with Dave Marchick, Dean of the Kogod School of BusinessFrom 3 Takeaways:The Genetic Revolution Has Begun - George Church on What Comes NextThe Transforming Power of Hospitality in Business: Setting the Table with Union Square Hospitality Group Founder & CEO Danny Meyer