Kimberly 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:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Kimberly on LinkedIn
• AI fun fact article
• On how Robert Plotkin addresses LLM regulation and legal advice for entrepreneurs
• Other episodes mentioned on the show:
  • AI as a Liberating Technology: Josh Bersin on Turning Routine Tasks into Superworkers Driving Trust, Creativity, and Growth
  • Dr. John Boudreau, future of work pioneer and former Cornell professor, discusses the new definition of work

In 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:

1. Mark McCrindle, Founder and Principal at McCrindle  – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/13014260
2. Pradeep Menon, CTO at Microsoft – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/13034974
3. Dave Kellogg, EIR at Balderton Capital – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/16665133
4. Alex Buder Shapiro, Chief People Officer at Jasper AI – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/17522593
5. Gary F. Bengier, Writer, philosopher, and technologist – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/12934217
6. Josh Bersin, Founder and CEO at The Josh Bersin Company – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/17863187
7. Bryan Power, Head of People at Nextdoor – Listen to the full conversation: https://www.buzzsprout.com/520474/episodes/16837259
8. 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)

Henrik 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:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Henrik on LinkedIn
• AI fun fact article
• How to Use Generative AI to Get Ahead In Your Career

Kelly 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

Eric 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:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Eric Cheng on LinkedIn
• AI fun fact article
• On How to raise over $200 million to detect audio deepfakes

Kate 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:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Kate on LinkedIn or at KO Insights
• AI fun fact article
• On How Unleashing Human Potential with AI

Sid 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

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Sid on LinkedIn
• AI fun fact article
• On Mastering Skills To Stay Relevant In the Age of AI

Darrick Horton is the CEO and co-founder of TensorWave, the company making waves in AI infrastructure by building high-performance compute on AMD chips. In 2023, he and his team took the unconventional path of bypassing Nvidia, a bold bet that has since paid off with nearly $150 million raised from Magnetar, AMD Ventures, Prosperity7, and others. TensorWave is now operating a dedicated training cluster of around 8,000 AMD Instinct MI325X GPUs and has already hit a $100 million revenue run rate.

Darrick is a serial entrepreneur with a track record of building infrastructure companies. Before TensorWave, he co-founded VMAccel, sold Lets Rolo to LifeKey, and co-founded the crypto mining company VaultMiner.

He began his career as a mechanical engineer and plasma physicist at Lockheed Martin’s Skunk Works, where he worked on nuclear fusion energy. While he studied physics and mechanical engineering at Andrews University, he left early to pursue entrepreneurship and hasn’t looked back since.

In this conversation we discussed:

• Why Darrick chose AMD over Nvidia to build TensorWave’s AI infrastructure, and how that decision created a competitive advantage in a GPU-constrained market
• What makes training clusters more versatile than inference clusters, and why TensorWave focused on the former to meet broader customer needs
• How Neocloud providers like TensorWave can move faster and innovate more effectively than legacy hyperscalers in deploying next-generation AI infrastructure
• Why power, not GPUs, is becoming the biggest constraint in scaling AI workloads, and how data center architecture must evolve to address it
• Why Darrick predicts AI architectures will continue to evolve beyond transformers, creating constant shifts in compute demand
• How massive increases in model complexity are accelerating the need for green energy, tighter feedback loops, and seamless integration of compute into AI workflows

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Darrick on LinkedIn
• AI fun fact article
• On How the new definition of work

Grant Lee is the CEO and co-founder of Gamma, the company reimagining presentations by building what some call the “anti-PowerPoint.” Since launching in 2022, Gamma has grown to 50 million users and reached $50M in annual recurring revenue. These milestones were achieved with just $12M in venture capital and a 30-person team. Before founding Gamma in 2020, Grant led finance at Optimizely, where he developed a passion for A/B testing. He began his career in investment banking and holds a BS in Biomechanical Engineering and an MS in Mechanical Engineering from Stanford University.

In this conversation, we discuss:

• How Gamma went from an idea to one of the fastest-growing presentation tools in the world with $50M ARR and a 30-person team
• Why Grant and his co-founders set out to reinvent slides from scratch instead of improving on PowerPoint
• Lessons from Optimizely that shaped Gamma’s culture of experimentation and rapid iteration
• How Grant thinks about product-market fit and why every feature must solve real user pain instead of mimicking the competition
• How AI serves as a design partner, not a replacement for human creativity, and why “human in the loop” is central to Gamma’s philosophy
• The importance of building user trust in generative AI through transparency, feedback loops, and community programs like the “Gambassador” initiative
• How resilience, early failures, and conviction helped Gamma survive investor rejection and a near-collapse during the SVB crisis

Dennis Kozak is the CEO of Ivanti, a leading enterprise IT and security company generating over $1 billion in annual revenue and serving more than 40,000 customers. He previously served as Ivanti’s COO after holding senior leadership roles at Avaya. Earlier in his career, Dennis spent nearly 23 years at CA Software (now Broadcom), where he led global partnership sales and services teams. He holds a BS in Accounting from St. Joseph’s University in Long Island.

In this conversation, we discuss:

• Dennis’s leadership journey from CA Technologies and Avaya to becoming CEO of Ivanti, and what prepared him to lead a billion-dollar IT security company
• Why convergence between cybersecurity and IT operations is accelerating, and how Ivanti is positioning itself at the center of that shift
• The impact of generative AI on IT support, including how Ivanti is building AI agents to handle routine tickets and empower human technicians
• How organizations can reduce cyber risk by closing visibility gaps and simplifying their tech stack
• The challenges of securing distributed workforces in a hybrid world, and why automation is critical to stay ahead of threats
• Why Dennis believes the future of enterprise IT is about blending user experience with security, not choosing between them

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Dennis on LinkedIn
• AI fun fact article
• On How to Reimagine Fan Experiences and Digital Transformation.

Jim Curry is the co-founder and CEO of BuildGroup, a venture firm based in Austin that has raised $330 million since its founding in 2015 and backed companies like Anaconda, Vidmob, DigniFi, and Benefitfocus. He brings more than two decades of experience in product, strategy, and corporate development from roles at Rackspace and Dell, and he co-founded OpenStack, one of the most widely used open source cloud computing platforms. Jim serves on the boards of Generation Serve and the University of Texas School of Undergraduate Studies. He holds degrees from UT Austin and Harvard Business School.

In this conversation, we discuss:

• Jim’s journey from Rackspace to launching BuildGroup and why he believes in “longer, slower capital” to support mission-driven founders
• How his experience co-founding OpenStack shaped his thinking on community-driven innovation and open-source software
• What AI startups can learn from the cloud era—and why infrastructure still matters in the age of foundation models
• Why Jim believes VCs often push startups to scale too fast and what sustainable growth looks like in practice
• The impact of AI on venture capital and how BuildGroup thinks about investing in software companies that solve real problems
• How founders can balance product vision with pragmatism, especially when building in volatile markets

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Jim on LinkedIn
• AI fun fact article
• On How to Develop NLP and AI Data Harvesting Using Games and Blockchains To Earn NFTs

George Maddaloni is the EVP and CTO for Operations at Mastercard, where he leads the performance and modernization of technology platforms serving more than 35,000 employees worldwide. He has previously held senior IT leadership roles at AIG, UBS, AT&T, GM, and Merrill Lynch, and currently serves on the board of SustainableIT.org. George earned his BS in Mechanical Engineering and Computer Science from Johns Hopkins University and an MBA from Fordham University.

In this conversation, we discuss:

• How Mastercard’s CTO thinks about the balance between innovation, trust, and regulation in one of the world’s most complex financial networks.
• The strategy behind modernizing Mastercard’s internal technology platforms to empower 35,000 global employees.
• Why a decade of AI experience changed how Mastercard approaches fraud, data, and customer confidence.
• The cultural shift that turned curiosity about AI into measurable progress across a global workforce.
• How a 50-year-old payments company keeps competing with startups by rethinking infrastructure from the ground up.
• George Maddaloni’s vision of the next era of payments and how technology might make transactions faster, safer, and nearly invisible.

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with George on LinkedIn
• AI fun fact article
• On How To Create an Energy-Based Work System that Empowers Employees
• Other resources mentioned in this conversation: On decentralized AI in Banks and the Future of Finance with Paolo Ardoino, Tether CEO 

Jon Levy is a behavioral scientist and New York Times bestselling author known for exploring trust, human connection, belonging, and influence. He’s the founder of The Influencers Dinner, a secret dining experience that has grown into a community of thousands of leaders, including Nobel laureates, Olympians, celebrities, executives, artists, and musicians. His book You’re Invited: The Art and Science of Connection, Trust, and Belonging was named a Wall Street Journal “Book of the Month” in 2021. He’s also the author of The 2 AM Principle: Discover the Science of Adventure and the newly released Team Intelligence: How Brilliant Leaders Unlock Collective Genius.

In this conversation, we discuss:

• Why the smartest teams often fail, and how trust, belonging, and psychological safety drive collective intelligence
• The surprising data behind team performance, including why individual IQ doesn’t predict group success
• What makes a team “brilliant,” and how leaders can design environments that unlock group flow and faster decision-making
• How AI changes team dynamics and why it’s urgent to redefine collaboration in a hybrid, tech-driven world
• The four principles of Team Intelligence and how they apply to both startups and global enterprises
• Jon’s personal journey from hosting secret dinners to writing Team Intelligence, and why he believes social bonds are the future of work

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Learn more of Jon on LinkedIn
• Explore Jon’s published work and speaking events
• AI fun fact article
• On How gen AI startups can beat Big Tech incumbents

Tracy Layney is a seasoned HR leader with more than 15 years of experience shaping people and culture strategies at Levi’s, Gap, and Shutterfly. She currently teaches Human Capital Strategy as an adjunct professor at the University of Chicago Booth School of Business. Tracy holds a BA in English from the University of Pennsylvania.

In this conversation, we discuss:

• Tracy shares her unconventional path from English major and aspiring lawyer to CHRO at Levi’s, Gap, and Shutterfly, and how consulting shaped her approach to organizational strategy.
• She reflects on lessons from working with iconic leaders like Eva Sage Gavin and Chip Bergh, including leading Levi’s through the early days of the pandemic.
• She explains why excellence and heart-centered leadership must coexist to build values-driven, high-performing cultures.
• She explores how AI and other disruptive forces are reshaping HR, from talent strategy to employee expectations, and why adaptability is critical for leaders.
• She discusses the importance of transparency and trust-building between HR and employees during times of uncertainty, drawing parallels with past crises.
• She shares her perspective as a professor on how future HR leaders are navigating unprecedented change, mental health challenges, and the rapid rise of AI in the workplace.

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Tracy on LinkedIn
• AI fun fact article
• On How To Democratize Content Creation using AI 

Sean Williams is the CEO and founder of AutogenAI, the world’s leading AI proposal-writing engine, launched in May 2022. Under his leadership, the company recently closed a nearly $40 million Series B round led by Salesforce Ventures. Prior to AutogenAI, Sean founded Corndel Ltd, where he served as Chief Executive and scaled the business to 350 employees before its $60 million acquisition by THI Holdings in 2020.

In this conversation, we discuss:

• Why Sean believes AI will revolutionize how organizations write, win, and deliver proposals
• How AutogenAI is reducing proposal writing time from days to hours for companies bidding on complex contracts
• The ethical considerations of AI-written proposals and why transparency is critical in high-stakes industries
• What Sean learned from scaling Corndel to 350 employees and how that experience shaped AutogenAI’s go-to-market strategy
• Why the biggest risk for organizations isn’t adopting AI too quickly, but failing to experiment early
• How AutogenAI is building trust with enterprise clients through customization, compliance, and human-in-the-loop design

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Sean on LinkedIn
• AI fun fact article
• On How To Prevent Bias and Be Responsible for Ethical Decision Making’s

Josh Bersin is one of the most respected voices in HR and HRTech, known for shaping how organizations think about talent, learning, and the future of work. He began covering the space in 2001 and later sold his firm, Bersin & Associates, to Deloitte in 2012. Today, he leads The Josh Bersin Company, which produces influential research, publishes widely on workplace trends, and hosts the annual Irresistible conference. He’s also the author of Irresistible: The Seven Secrets of the World’s Most Enduring, Employee-Focused Organizations and the host of a podcast that explores the evolving world of work with clarity and insight.

In this conversation, we discuss:

• Why fears of AI-driven job loss are overstated and how automation can unlock new opportunities for growth.
• The rise of “superworkers” who use AI to eliminate routine tasks and focus on creativity, innovation, and more meaningful contributions.
• How companies are rethinking organizational design, roles, and skills in response to rapid advances in AI.
• Real-world examples of AI adoption in banking, insurance, and airlines—and what leaders can learn from them.
• The concept of “supermanagers” and why human leadership and soft skills remain critical in an AI-powered workplace.
• Josh’s perspective on what it means to be an “irresistible organization” in a time of massive technological and cultural change.

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Josh on LinkedIn
• AI fun fact article
• On How To Invest on AI Driven Work
• Past Episode with Josh [Season 3, #278]: On How the Best-Performing Teams use AI

Jody Glidden is the CEO and founder of Postilize, a company focused on reinventing CRM through AI. Before launching Postilize, he co-founded Introhive and served as CEO until 2022, helping raise over $100 million to build the enterprise relationship management category. A serial entrepreneur, Jody previously founded icGlobal, which was acquired by Smartforce, and played a key role in scaling Chalk Media, later acquired by BlackBerry maker Research in Motion. He holds a BBA from the University of New Brunswick and a Master’s in Information Systems from Harvard.

In this conversation, we discuss:

• Why traditional CRMs fail to reflect how relationships actually evolve—and how Postilize is addressing that gap
• How Postilize handles privacy, hallucinations, and human oversight to stay useful without crossing ethical lines
• Jody’s approach to using AI not to replace human connection, but to augment and scale authentic relationship building
• How relationship intelligence helps sales and go-to-market teams understand who to engage, when, and why
• Why keeping CRMs accurate is nearly impossible without automation and real-time enrichment
• What Jody learned from building Introhive and why Postilize is taking a radically different approach
• The future of CRM as a system of engagement rather than just a system of record

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Jody on LinkedIn
• AI fun fact article
• On How To Manage Enterprise Apps That Support Thousands of Employees for a Rapidly Growing Global Company.

Anthony Moisant is the Chief Information Officer (CIO) and Chief Security Officer (CSO)  at Indeed, the world’s leading job site with over 610 million job seeker profiles. He joined Indeed nearly five years ago after serving in a similar role at sister company Glassdoor for eight years. As CIO, he leads the teams responsible for the internal technology that supports employees and drives the business. As CSO, he oversees the security team focused on protecting the data of job seekers, customers, and employees. Anthony is also a graduate of the U.S. Navy Nuclear Submarine School.

In this conversation, we discuss:

• Indeed’s goal to cut time-to-hire by 50% by removing friction across systems and workflows.
• Solving the hiring resume glut so every application gets seen and answered, using AI to improve matching and follow-ups.
• Why skills (not degrees) will define the future of hiring, and how job seekers can prepare for a skill-first economy
• How to double team productivity with AI while keeping trust high and addressing fears about automation.
• A values-driven approach to AI ethics: transparency, fairness testing, red-teaming models, and an “AI constitution” agent.
• The lessons Anthony brought from the U.S. Navy and how they continue to shape his leadership approach in high-pressure environments

Resources:

• Subscribe to the AI & The Future of Work Newsletter
• Connect with Anthony on LinkedIn
• AI fun fact article
• On How to Invest and Advise Early Stage Tech Companies