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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 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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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 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:

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

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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)