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Dan Turchin


Host Dan Turchin, PeopleReign CEO, explores how AI is changing the workplace. He interviews thought leaders and technologists from industry and academia who share their experiences and insights about artificial intelligence and what it means to be human in the era of AI-driven automation. Learn more about PeopleReign, the system of intelligence for IT and HR employee service: http://www.peoplereign.io.


AI and the Future of Work

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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.

375: How AI Is Changing Healthtech Investing, According to Define Ventures’ Lynne Chou O’Keefe

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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 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

374: Dave Kellogg Unpacks the 2026 Predictions on SaaS, AI, and Trust

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Lynn Thoman is a professor at Columbia University’s School of International and Public Affairs and the founder of 3 Takeaways, a top 1% global podcast known for distilling big ideas from influential leaders shaping policy, business, and society. 

Drawing on experience across corporate strategy, public sector advisory work, and board service at institutions such as the Brookings Institution and Harvard’s Kennedy School of Government, Lynn brings a cross-sector lens to how AI is reshaping decision-making, learning, and human potential.

In this conversation, we discuss:

 • Why AI is best understood as an amplifier of human capability, especially in leadership, where judgment and choices matter more than technology.
 • How the real upside of AI is giving people more space for imagination, empathy, and meaningful human connection.
 • How to prepare students and professionals for an AI-shaped job market by prioritizing learning paths, adaptability, and relationships over fixed career tracks.
 • Why the biggest risks of AI come from small, hard-to-detect changes in data or models that can create serious downstream harm.
 • How AI is pushing education, work, and leadership back toward core human skills like judgment, curiosity, and imagination.
 • Where cautious optimism comes from, including AI’s potential to expand access to knowledge, healthcare, and opportunity when used with care.

Resources:

Subscribe to the AI & The Future of Work NewsletterConnect with Lynn on LinkedInAI fun fact articleOn How genAI studios launch AI-first companies
Other podcast episodes mentioned on the show:

On reinventing the academic curriculum for MBAs with Dave Marchick, Dean of the Kogod School of BusinessFrom 3 Takeaways:The Genetic Revolution Has Begun - George Church on What Comes NextThe Transforming Power of Hospitality in Business: Setting the Table with Union Square Hospitality Group Founder & CEO Danny Meyer

373: From Credentials to Curiosity: Why Learning Paths Matter More Than Career Paths, with Columbia Professor Lynn Thoman

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Every January 24, the world celebrates the International Day of Education, a reminder that learning remains one of the most powerful drivers of opportunity, mobility, and social progress.

In this special compilation episode of AI and the Future of Work, we revisit conversations with education leaders, university deans, and workforce innovators exploring how AI is transforming learning, access, credentials, and lifelong education.

From academic integrity and digital classrooms to reskilling and future-ready education models, this episode highlights one essential truth: technology can accelerate learning, but education must remain human-centered.

Featuring insights from:

 • Chris Caren (CEO, Turnitin) - Listen to the full conversation here: 
https://aiandthefutureofwork.buzzsprout.com/520474/episodes/15780222 • 
 • Marni Baker Stein (Chief Content Officer, Coursera) - Listen to the full conversation here: 
https://aiandthefutureofwork.buzzsprout.com/520474/episodes/17359747 • 
 • Dave Treat (Chief Technology Officer, Pearson) - Listen to the full conversation here: 
https://aiandthefutureofwork.buzzsprout.com/520474/episodes/17557154 • 
 • Dave Marchick (Dean, Kogod School of Business, American University) - Listen to the full conversation here: 
https://aiandthefutureofwork.buzzsprout.com/520474/episodes/17119724 • 
 • Gary Bolles (Chair for the Future of Work, Singularity University) - Listen to the full conversation here: 
https://aiandthefutureofwork.buzzsprout.com/520474/episodes/9236086 • 

What You’ll Learn:

 • How AI is reshaping education and digital learning models
 • Why academic integrity matters more than ever in the age of generative AI
 • How universities and platforms expand access to global education
 • Why lifelong learning and reskilling are becoming essential career skills
 • How educators prepare students for future work and leadership
 • Which human skills remain critical in an AI-driven economy

Inspired by something you heard?
Share this episode with someone passionate about education and the future of learning. And don’t forget to subscribe for more conversations with the leaders shaping the future of 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)365: What We’ve Learned from 364 Expert Conversations (Special Episode)

AI and Education: How Artificial Intelligence Is Transforming Learning (International Day of Education Special Episode)

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Amit 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:

Subscribe to the AI & The Future of Work NewsletterConnect with Amit on LinkedInAI fun fact articleOn How AI Is Changing Finance: Data Challenges, Collaboration, and Future Trends with Mike Schuster • Other episode mentioned in the show:
On AI Design Philosophy and Building the Anti-PowerPoint with Grant Lee, CEO of Gamma

372: From CRM Data to Revenue AI: How Sales Is Being Rebuilt with Gong Co-Founder and CEO Amit Bendov

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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 NewsletterConnect with Kimberly on LinkedInAI fun fact articleOn how Robert Plotkin addresses LLM regulation and legal advice for entrepreneursOther episodes mentioned on the show:AI as a Liberating Technology: Josh Bersin on Turning Routine Tasks into Superworkers Driving Trust, Creativity, and GrowthDr. John Boudreau, future of work pioneer and former Cornell professor, discusses the new definition of work

371: From Generic Training to AI-Personalized Learning at Work with Kimberly Williams, Absorb Software CEO

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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 NewsletterConnect with Henrik on LinkedInAI fun fact articleHow to Use Generative AI to Get Ahead In Your Career

370: AI Can Build the Company. Only Humans Can Build the Bond | BARK Co-Founder Henrik Werdelin

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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 NewsletterConnect with Kelly Jones on LinkedInAI fun fact articleOn 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

369: Why Trust Is the Currency of Work in the Age of AI with Cisco CPO Kelly Jones

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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 NewsletterConnect with Eric Cheng on LinkedInAI fun fact articleOn How to raise over $200 million to detect audio deepfakes

368: Match Humans, Not Keywords: Inside Jobright’s AI Talent Matching with Serial Entrepreneur Eric Cheng

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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 NewsletterConnect with Kate on LinkedIn • or at 
KO InsightsAI fun fact articleOn How Unleashing Human Potential with AI

373: From Credentials to Curiosity: Why Learning Paths Matter More Than Career Paths, with Columbia Professor Lynn Thoman

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