Advertise on podcast: AI and the Future of Work: Artificial Intelligence in the Workplace, Business, Ethics, HR, and IT for AI Enthusiasts, Leaders

Send us Fan Mail In this special April compilation episode of AI and the Future of Work, we’re bringing back six great former guests who published popular books about how AI is redefining humans at work.  The future of work isn't about competing with algorithms. It’s about how we use technology to increase our capacity for trust, express our vulnerability, and discover meaning. This episode brings together insights from authors who explore how AI is reshaping work and what it means for individuals and organizations.  What You’ll Learn Why delegating routine tasks to AI frees us to explore our human superpowers like empathy, rational thinking, and compassion.How the future of knowledge work lies in navigating ambiguity and expressing entirely new ideas.Why leaders must move beyond monitoring and productivity theater to build cultures of trust and give teams the space to experiment.How the traditional, contract-based employment model is failing the next generation and what replaces it.Why the era of the “superhuman” leader is over, and how showing your human side earns loyalty in times of disruption.How the AI revolution is sparking a massive work quake, and why only you can write your own story and decide what gives you meaning.Featured Guests Bernard Marr, Futurist and Bestselling Author of Generative AI in Practice - Listen to the full conversation here: [https://www.buzzsprout.com/520474/episodes/15441666] Atif Rafiq, Former Fortune 500 Executive and Author of Decision Sprint - Listen to the full conversation here: https://www.buzzsprout.com/520474/episodes/14507445] Brian Elliott, Executive Advisor and bestselling author of "How the Future Works". - Listen to the full conversation here: [https://www.buzzsprout.com/520474/episodes/17282891] Josh Drean, Co-founder of the Work3 Institute and Co-author of Employment is Dead - Listen to the full conversation here: [https://www.buzzsprout.com/520474/episodes/16473644] Linda Rottenberg, CEO and Co-founder of Endeavor, and Author of Crazy is a Compliment - Listen to the full conversation here: [https://www.buzzsprout.com/520474/episodes/8356582] Bruce Feiler, Bestselling Author of The Search: Finding Meaningful Work in a Post-Career World - Listen to the full conversation here: [https://www.buzzsprout.com/520474/episodes/14158168] 💬 Inspired by something you heard in this episode? Share your favorite insight about redefining work, building trust, or finding meaning in the AI era, and tag us on social.  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 authors and leaders shaping what comes next.

Send us Fan Mail Oren Michels is an entrepreneur, investor, board member, and advisor to technology startups in the US and Europe. He is the co-founder and CEO of Barndoor AI, the control plane for agentic AI, and the founder who previously helped define the API management category with Mashery, acquired by Intel in 2013. He is also a Tony-nominated Broadway and Off-Broadway producer whose credits include Romeo+Juliet and Good Night, and Good Luck starring George Clooney. In this episode, Oren draws on two decades of building foundational infrastructure for the enterprise to make the case that governing AI agents is not a security problem. It is an entirely new category of problem, and most companies do not yet have the vocabulary to describe it, let alone the tools to solve it.  If your agents can already write to your CRM, interpret your instructions, and act without life experience or fear of consequences, who is actually in control? In this conversation, we discuss: Why securing AI agents is entirely different from managing APIs, and why traditional security and identity access tools were never designed to handle what agents can do.The reason most so-called agentic AI is still glorified robotic process automation, and what it will actually take to unlock enterprise value.How Barndoor AI's "least privilege" framework for agents works, and why the permission logic goes far beyond the identity of the human using the tool.Why an agent with delete access to your CRM is one probabilistic misfire away from a catastrophic outcome, and why ultimate responsibility always comes back to the humans operating the tools.The BYO AI parallel to BYOD: why well-meaning employees using personal AI tools with company data may force the enterprise governance moment no one is ready for.Why the same instinct that took Oren from API infrastructure to Broadway and back to enterprise AI may be exactly the mindset the agentic era demands from its builders.Explore this conversation: 00:00 Intro and fun Fact 03:46 Oren Michels's Path From API Management to Building Barndoor AI 05:44 Redefining Trust: AI Lacks Life Experience and Fear of Consequences 08:24 History Repeating: Why AI Needs a Control Plane Just Like APIs Did 12:35 Deterministic APIs vs. Probabilistic Agents: Why Governing AI Is a Social Challenge 18:25 How Barndoor AI's "Least Privilege" Framework for Agents Actually Works 20:50 The Token Economy and Context Windows: Wandering Into the AI Home Depot 25:25 Preventing Catastrophic Failures: Why AI Agents Should Never Have Delete Access 31:39 The BlackBerry Moment of AI: Navigating the "BYO AI" Enterprise Trend 38:04 Balancing Tech and Creativity: From Enterprise AI to Producing on Broadway Resources Subscribe to the AI & The Future of Work NewsletterConnect with Oren on LinkedInAI fun fact articleOn How AI may eliminate jobs: what the data reveals

Send us Fan Mail Jake Saper is a General Partner at Emergence Capital, one of the most iconic venture firms in enterprise software, with a portfolio that includes Zoom, Gusto, Veeva, and Together AI. Emergence has backed some of the most category-defining B2B companies of the last two decades, and Jake has spent nearly 12 years at the center of that deal flow. What sets Jake apart is a life lived on both sides of the creativity question: he backs the companies building AI but also performs across genres from blues to metal as a working musician. In this episode, Jake brings that rare combination of investor rigor and artist instinct to one of the hardest questions AI is forcing us to face, and whether you leave reassured or unsettled may depend entirely on how much of your identity is wrapped up in the work you create. In this conversation, we discuss: How AI will democratize the creation of art but commoditize its execution, ultimately causing the value of live, dynamic human performances to skyrocket.The stunning acceleration of startup growth, with top-quartile B2B software companies now scaling from zero to $1 million in ARR in just four months.How the flood of AI-generated content is turning attention into the real bottleneck, and why curation and point of view become the new competitive advantage.Why Jake believes the market will self-regulate the anthropomorphization of AI agents in the workplace, and where that logic has a hard limit.What Geoffrey Hinton said about building AI "like a mother," why it was both comforting and deeply unsatisfying, and what it reveals about AGI risk.Why Jake argues disclosure matters during this transition period, but what he actually wants people to ask about art as AI becomes a normal creative tool.Explore this conversation: 00:00 Why AI Makes It Easier to Build a Demo and Harder to Build a Moat 05:25 From Cell Towers to Venture Capital: Jake Saper's Path to Emergence 08:53 How AI Is Compressing Startup Growth: From 18 Months to 4 Months to $1M ARR 18:05 What Art Actually Is: Compressed Human Experience and the Act of Making Meaning Shareable 23:30 How AI Can Unlock Latent Creativity in People Who Don't Think of Themselves as Creators 26:55 Why Disclosure Matters When Trust and Authenticity Are at Stake 30:19 Navigating a Post-Truth Era: When Everything Looks Synthetic, What Do We Believe? 32:14 Why the Value of Live Performance Is About to Skyrocket 35:58 As Soulless Entities Multiply, Soul-to-Soul Human Connection Becomes More Valuable 40:38 What Geoffrey Hinton Said About Building AI "Like a Mother" and Why It Was Unsatisfying 43:04 Why the Most Enduring Art Has Always Been About Transfer, Not Authorship Resources: Subscribe to the AI & The Future of Work NewsletterConnect with Jake on LinkedInAI fun fact articleOn How AI Is Revolutionizing Creativity in Art, Music, and Education

Send us Fan Mail Daniel Lereya is Chief Product and Technology Officer at monday.com, the AI work platform trusted by 60% of the Fortune 500 and valued at approximately $8 billion. He joined the company when it had 30 people and $4.5M ARR, and has since grown his team from 5 to nearly 900 people as monday.com crossed $1 billion in ARR. In this episode, Daniel draws on nearly a decade of scaling one of the world's most adopted work platforms to share what it actually takes to rebuild product thinking from scratch when AI changes everything you thought you knew. In this conversation, we discuss: Why the instincts that made monday.com successful are the exact ones Daniel says had to be dismantled to build AI-first products.What the critical difference is between building a demo that impresses and an agent that actually works in production, and where most teams get it wrong.Why Daniel believes wrapping AI inside rigid workflows produces better results than giving agents full discretion, and what monday.com learned the hard way.What happened when 2,000 of 3,000 monday.com employees started building their own apps in just two weeks, and what it revealed about the future of who gets to build software.Why Daniel argues that when an AI agent makes a mistake, the real question leaders should be asking has nothing to do with the technology.Why the biggest barrier to AI adoption is not the technology itself, and what Daniel says companies must stop waiting for before they start.Explore: 00:00 Why AI Adoption Is Harder Than It Looks 00:53 Introduction + AI Commerce Standards: Google, OpenAI & Visa 04:30 Daniel Lereya's 9-Year Journey Scaling monday.com to $1B ARR 09:00 How AI Forces a Complete Reset in Product Thinking 12:25 The "AI Month" Initiative: Pausing R&D to Rebuild from Scratch 14:57 Building AI Products When the Output Is Non-Deterministic 20:47 What 250,000 Customers Taught Us About AI in the Real World 25:38 Responsible AI: Guardrails, Governance, and Data Control 31:28 Who Is Responsible When an AI Agent Makes a Mistake? 37:04 The Future of Work: Humans, Agents, and What Comes Next Resources: Subscribe to the AI & The Future of Work NewsletterConnect with Daniel on LinkedInAI fun fact articleOn How we can take back control from Big Techhttps://peoplereign.io/podcast/

Send us Fan Mail Lisa Davis is a technology executive who has served as CIO and tech leader for some of the world's most complex organizations, including Intel, Blue Shield of California, the U.S. Marshals Service, and the Department of Defense.  She is now focused on shaping the next generation of leaders and advocating for women and diverse talent in STEM through her board work, executive coaching, and her forthcoming book, The Only Woman in the Room: How to Win in a Workplace Still Built for Men. In this episode, Lisa draws on 30+ years leading technology at the highest levels of government and enterprise to make the case that the future of AI depends on who gets to build it, and as long as women remain locked out of those rooms, we are getting it dangerously wrong. In this conversation, we discuss: Why women's representation in STEM has fallen from 34% in the mid-1980s to 22% today, and why that decline is a crisis for the future of AI, not just the workplace.Why the real risk isn't the technology itself but the leadership teams making AI decisions without diverse voices at the table.The structural systems that were never designed for women to thrive, and why redesigning them is a business imperative, not a social favor.Why current corporate layoffs are being falsely attributed to AI, and what leaders need to start saying out loud.Why girls begin dropping out of math and science as early as middle school, how cultural norms around "bossiness" suppress leadership potential, and what parents and organizations can do to intervene earlier.What Lisa says women who finally reach the executive table must do differently, and why most don't.Resources: Subscribe to the AI & The Future of Work NewsletterConnect with Lisa on LinkedIn or visit her website to learn more about her book.AI fun fact articleOn how to navigate life transitions with Bruce Feiler, award-winning author and popular TEDx speaker 

Send us Fan Mail James Cham is a Partner at Bloomberg Beta, the venture capital firm recognized by CB Insights as the #2 investor in AI. He has spent years backing the companies quietly building the infrastructure of tomorrow's economy, including Orbital Insight, Primer, Domino Data Labs, and AppZen.  A Harvard CS graduate and MIT MBA, James brings a rare combination of technical depth, philosophical seriousness, and long-horizon investing perspective to every conversation.  In this episode, he challenges some of the most popular  assumptions in enterprise AI adoption (including the idea that keeping humans in the loop is always the right answer) and makes a compelling case for why the moral and economic decisions we make right now will shape the nature of work for the next hundred years. In this conversation, we discuss: Why the people who benefit from AI models, not those impacted by them, should bear full legal and moral responsibility for the harms they causeWhy comparing AI to a flawless "Platonic ideal" is a mistake, and how the mathematical consistency of models is a massive advantage over noisy, unpredictable human decision-makingThe case for pulling humans out of the loop and why romanticizing your role in the process is exactly how organizations miss the real opportunityWhy corporate America's "gold star" approach to AI adoption, tracking how many employees used AI once this week, is a dangerous distraction from what heavy users are already doingHow ancient wisdom and the biblical concept of creation in Genesis can help us navigate the moral responsibilities of building new technologiesJames’s three massive investment theses, including the untapped market for AI tools with high emotional intelligence and why developers spending over $50 a day on tokens are already living in the futureResources: Subscribe to the AI & The Future of Work NewsletterConnect with James on LinkedInAI fun fact articleOn How AI Impacts Humanity

Send us Fan Mail Adrian 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 us Fan Mail To 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 Guests Charlene 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 Learn Why 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 Mail Matt 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 Mail Kourtney 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 Mail Scott 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 Mail In 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 Guests Eric 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 Learn Why 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 Mail Andrea 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 Mail Lynne 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 Mail Dave 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 Chapters 00:00 Why Dave Kellogg’s Annual SaaS Predictions Matter More Every Year 03:53 Working for the Algorithm, Not the Other Way Around 06:10 “Death of SaaS”: Why Enterprise Software Isn’t Going Away 08:56 Why Enterprise Software Is Built to Last 11:51 AI and Jobs: Why Work Disappears Differently Than We Expect 16:31 The New Jobs AI Creates and Why Humans Stay Essential at Work 19:22 Why Trust Becomes the Most Valuable Currency in an AI-Driven World 24:23 Why AI Forces Us to Rethink Trust, Media, and Credibility 27:57 Why the Rule of 60 Is Replacing the Rule of 40 for Startups in 2026 33:44 How Venture Capital Is Becoming a Financial Services Business 41:47 Why Silicon Valley’s New Willingness to Take Political Positions Surprised Many Founders 45:57 What the Grateful Dead Can Teach Us About Business, Creativity, and Legacy Resources: 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