AI and the Future of Work
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Episode Number : 384
Jake Saper is a General Partner at Emergence Capital, one of the most iconic venture firms in enterprise
Show moreShow lessJake 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 AuthorshipResources:
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Episode Number : 383
Daniel Lereya is Chief Product and Technology Officer at monday.com, the AI work platform trusted by 60% of
Show moreShow lessDaniel 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.
Resources:
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Episode Number : 382
Lisa Davis is a technology executive who has served as CIO and tech leader for some of the
Show moreShow lessLisa 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 Newsletter
- Connect with Lisa on LinkedIn or visit her website to learn more about her book.
- AI fun fact article
- On how to navigate life transitions with Bruce Feiler, award-winning author and popular TEDx speaker
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Episode Number : 381
James Cham is a Partner at Bloomberg Beta, the venture capital firm recognized by CB Insights as the
Show moreShow lessJames 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 cause
- Why 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-making
- The case for pulling humans out of the loop and why romanticizing your role in the process is exactly how organizations miss the real opportunity
- Why 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 doing
- How ancient wisdom and the biblical concept of creation in Genesis can help us navigate the moral responsibilities of building new technologies
- James’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 future
Resources:
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Episode Number : 380
Adrian McDermott is Chief Technology Officer at Zendesk, where he leads the company’s product management and engineering teams
Show moreShow lessAdrian 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 safety
- The 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:
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Episode Number : 379
Matt Britton is Founder and CEO of Suzy and a leading voice on how AI and generational change
Show moreShow lessMatt 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:
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Episode Number : 378
Kourtney Cross is a RiseUp with ServiceNow Graduate and Business Analyst at Leidos. With a background in accounting
Show moreShow lessKourtney 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:
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Episode Number : 374
Dave Kellogg is a leading voice in enterprise software, SaaS metrics and go-to-market strategy. A four-time guest on
Show moreShow lessDave 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 Newsletter
- Connect with Dave Kellogg on LinkedIn
- Kellblog Predictions for 2026
- AI fun fact article
- On How AI is Making Networks Smart
- Previous 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
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Episode Number : 377
Scott Strickland is Chief Commercial Officer at Wyndham Hotels & Resorts and former Chief Information Officer of Wyndham
Show moreShow lessScott 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:
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Episode Number : 376
Andrea Iorio is one of Brazil’s most requested keynote speakers on digital transformation, innovation, and leadership. His work
Show moreShow lessAndrea 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:
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Episode Number : 375
Lynne Chou O’Keefe is the Founder and Managing Partner of Define Ventures, one of the largest early-stage health
Show moreShow lessLynne 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:
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Episode Number : 373
Lynn Thoman is a professor at Columbia University’s School of International and Public Affairs and the founder of
Show moreShow lessLynn 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 Newsletter
- Connect with Lynn on LinkedIn
- AI fun fact article
- On How genAI studios launch AI-first companies
Other podcast episodes mentioned on the show:
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Episode Number : 372
Amit Bendov is the co-founder and CEO of Gong, the revenue AI platform he started in 2015 after
Show moreShow lessAmit Bendov is the co-founder and CEO of Gong, the revenue AI platform he started in 2015 after realizing that traditional CRM systems tracked outcomes but failed to explain why deals were won or lost. That insight led him to focus on customer conversations as the missing source of truth in sales. Since its founding, Gong has raised more than $580 million and reached a valuation of $7.25 billion. Today, Gong helps sales teams reduce manual work, improve performance, and better understand what customers are actually saying.
In this conversation, we discuss:
- Why traditional CRM systems track what happened but fail to explain why deals are won or lost, and how that gap led to the rise of Revenue AI as a new category.
- How Gong’s Revenue AI differs from CRM by analyzing sales conversations, reducing manual admin work, and actively helping sellers prepare, follow up, and improve performance in real time.
- The emotional cost of sales work, and how using AI to remove administrative burden improves both sales results and seller job satisfaction.
- What it takes to build trust in AI tools that analyze customer conversations, including data stewardship, transparency, and delivering clear value to sellers.
- How an AI-first product vision can exist years before the technology is ready, and what it means to design systems for autonomy rather than simple automation.
- The reality behind “overnight success,” including early product-market fit tests, paid pilots that felt risky, and navigating growth slowdowns without abandoning the original vision.
Resources:
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Episode Number : 371
Kimberly Williams is CEO of Absorb Software, where she helps over 3,000 organizations deliver smarter learning experiences to
Show moreShow lessKimberly Williams is CEO of Absorb Software, where she helps over 3,000 organizations deliver smarter learning experiences to 34 million employees. She brings decades of leadership in enterprise tech and now sits at the center of how AI is changing the way people grow at work. In this episode, Kimberly shares how learning becomes more powerful when it’s personalized, embedded in daily workflows, and led by curious teams who treat culture as a competitive advantage.
In this conversation, we discuss:
- How AI is shifting corporate learning from generic training programs to personalized, in-the-flow development tailored to each employee’s needs.
- Why in-context learning matters more than traditional courses, and how AI coaching inside tools like Slack, Salesforce, or ServiceNow changes how people actually learn at work.
- What it means to turn L&D teams into AI model trainers who encode company culture, values, and knowledge into coaching experiences.
- How Absorb Software tracks AI usage across teams and uses dashboards and leaderboards to drive internal adoption.
- The role of outcome data in modern learning systems, and how tying learning directly to performance metrics changes what training gets delivered.
- The advice Kimberly gives early-career talent, especially women, about finding roles where their contributions are measurable and their growth is supported by culture, not just credentials.
Resources:
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Episode Number : 365
In this special episode of AI and the Future of Work, host Dan Turchin looks back on what 365
Show moreShow lessIn this special episode of AI and the Future of Work, host Dan Turchin looks back on what 365 conversations have revealed about how AI is reshaping the way we work.
What themes have emerged most consistently? Which ideas connect founders, researchers, and operators across industries? And what have these discussions taught us about the evolving relationship between humans and intelligent systems?
Featuring Guests:
- Mark McCrindle, Founder and Principal at McCrindle – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/13014260
- Pradeep Menon, CTO at Microsoft – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/13034974
- Dave Kellogg, EIR at Balderton Capital – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/16665133
- Alex Buder Shapiro, Chief People Officer at Jasper AI – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/17522593
- Gary F. Bengier, Writer, philosopher, and technologist – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/12934217
- Josh Bersin, Founder and CEO at The Josh Bersin Company – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/17863187
- Bryan Power, Head of People at Nextdoor – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/16837259
- Dave Treat, Chief Technology Officer at Pearson – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/17557154
💡 What You Will Learn
- Why the future of work remains human-centered
- How AI amplifies human capability rather than replacing it
- Why trust and transparency define successful AI-driven teams
- How workplace culture is evolving as organizations adopt AI
- Why meaning, empathy, and lifelong learning matter more than ever
💬 Inspired by this episode?Share your favorite insight on social media and tag us (https://www.instagram.com/aifutureofwork/)
And remember to subscribe for more conversations with the leaders shaping the future of AI and work.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)
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Episode Number : 370
Henrik Werdelin is a founder and investor who has spent more than a decade building companies at the
Show moreShow lessHenrik Werdelin is a founder and investor who has spent more than a decade building companies at the intersection of culture, technology, and consumer behavior. He co-founded BARK, the public company that redefined how millions of dog parents connect with their pets, and Prehype, the startup studio behind brands like Ro and Audos.
In this episode, Henrik explores how founders can embrace AI without losing human connection, drawing from his experience as co-host of Beyond the Prompt and co-author of Me, My Customer and AI.
Recognized by Fast Company and Business Insider for his creative impact, Henrik shares a practical perspective on building companies that scale while staying deeply human.
In this conversation, we discuss:
- Why Henrik believes founders must stay close to users and how AI can deepen (not dilute) human connection.
- What “building companies at the edge of culture” means and why authenticity beats scale when designing for trust.
- How Henrik and his team use AI to speed up product development without compromising on creativity or purpose.
- The shift from storytelling to “storylistening” and how paying attention to customer behavior shapes better products.
- What the best founders get wrong about generative AI and why Henrik advocates for a more mindful approach to adoption.
- How roles inside companies are evolving in response to AI and what leaders can do to support creative experimentation.
Resources:
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Episode Number : 369
Kelly Jones is Chief People Officer at Cisco, where she leads the people strategy for more than 84,000
Show moreShow lessKelly Jones is Chief People Officer at Cisco, where she leads the people strategy for more than 84,000 employees worldwide. Over nearly two decades, she has helped make Cisco a global benchmark for workplace culture. In this episode, Kelly explains why trust is the foundation of every AI strategy, how Cisco is equipping managers for an era of augmented work, and what it takes to lead responsibly when the pace of change is this fast.
In this conversation, we discuss:
- Why trust is Cisco’s most valuable workplace currency and how it shapes decisions about AI, culture, and leadership.
- How AI becomes a co-pilot when employees are given the safety, training, and time to explore new tools at their own pace.
- What “super leadership” looks like and the four traits Cisco’s CPO believes will define successful managers in an AI-augmented workplace.
- How Cisco evaluates AI use cases based on disruption, scale, and their potential to enhance the employee experience.
- Why the real opportunity of AI lies in automating administrative work to give humans more time for purpose, creativity, and connection.
- The systems Cisco is building to ensure responsible AI use through governance, upskilling, and clear ethical boundaries.
Resources:
- Subscribe to the AI & The Future of Work Newsletter
- Connect with Kelly Jones on LinkedIn
- AI fun fact article
- On How to Use Generative AI to Get Ahead In Your Career
- Other episode mentioned in the show: AI as a Liberating Technology: Josh Bersin on Turning Routine Tasks into Superworkers Driving Trust, Creativity, and Growth
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Episode Number : 368
Match Humans, Not Keywords: Inside Jobright’s AI Talent Matching with Serial Entrepreneur Eric Cheng
Eric Cheng is co-founder and CEO of Jobright, the AI career copilot serving more than 550,000 users. After
Show moreShow lessEric Cheng is co-founder and CEO of Jobright, the AI career copilot serving more than 550,000 users. After building core backend systems at Box and scaling Fangcloud to acquisition, he turned his focus to fixing what’s broken in hiring. His perspective blends engineering depth with a human-centered approach to matching talent and opportunity.
In this conversation we discussed:
- Why Eric created Jobright after interviewing 150 young professionals and discovering a gap in personalized job search support.
- How Jobright reframes hiring as a “matching” problem and uses AI to function more like a career coach than a job board.
- The limitations of keyword-based search tools and how AI enables more nuanced, human-like job matching.
- Why building trust matters in AI-powered hiring platforms and how Jobright balances efficiency with authenticity and accuracy.
- What the “learning loop” means for job seekers and why Eric believes the mindset shift matters more than the résumé.
- How emerging roles like AI operations and forward deployment engineers reflect deeper changes in how organizations adopt and manage AI.
Resources:
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Episode Number : 367
Kate O’Neill is a leading voice on AI and tech humanism, known for helping organizations build more meaningful,
Show moreShow lessKate O’Neill is a leading voice on AI and tech humanism, known for helping organizations build more meaningful, human-centered futures. She has been featured by outlets like BBC, NPR, and NBC, and serves on the United Nations AI advisory board. A CX Hall of Fame inductee and award-winning entrepreneur, Kate brings a unique blend of optimism and realism to conversations about AI, data, and the future of work. Her latest book, What Matters Next, explores how to make human-friendly tech decisions.
In this conversation we discussed:
- How tech humanism explains the relationship between people, technology, and business, and how leaders can design AI systems that strengthen the alignment
- Why humans project intelligence and agency onto AI tools, and what it takes to build healthy, intentional habits around emerging technologies
- Practical ways workers can use AI to elevate their roles rather than fear automation
- The role of leadership in creating psychologically safe environments where employees can openly experiment with AI tools
- The risk of designing systems that lead to “automated bureaucracy,” and how organizations can embed meaning into automated experiences at scale
- Why meaning and purpose remain uniquely human, and how future workplaces can evolve by pairing human judgment with increasingly capable AI systems
Resources:
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Episode Number : 366
Sid Sheth is the CEO and co-founder of d-Matrix, the AI chip company making inference efficient and scalable
Show moreShow lessSid Sheth is the CEO and co-founder of d-Matrix, the AI chip company making inference efficient and scalable for datacenters. Backed by Microsoft and with $160M raised, Sid shares why rethinking infrastructure is critical to AI’s future and how a decade in semiconductors prepared him for this moment.
In this conversation, we discuss:- Why Sid believes AI inference is the biggest computing opportunity of our lifetime and how it will drive the next productivity boom
- The real reason smaller, more efficient models are unlocking the era of inference and what that means for AI adoption at scale
- Why cost, time, and energy are the core constraints of inference, and how D-Matrix is building for performance without compromise
- How the rise of reasoning models and agentic AI shifts demand from generic tasks to abstract problem-solving
- The workforce challenge no one talks about: why talent shortages, not tech limitations, may slow down the AI revolution
- How Sid’s background in semiconductors prepared him to recognize the platform shift toward AI and take the leap into building D-Matrix
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