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