Fewer Jobs, Higher Pay: The AI Compensation Paradox

Kyle Holm has spent 25 years advising companies on compensation, and right now he’s watching the logic of corporate hierarchy break in real time. Not because executives suddenly discovered organizational theory, but because AI is collapsing the distance between capability and influence. The old model—slow progression through management layers, credential accumulation, carefully staged promotions—is running into a technology that rewards direct value creation instead. And executives are noticing.In this conversation from Transform Las Vegas, Kyle and David unpack what happens when AI-native companies stop hiring “mid-level” talent altogether, why compensation systems built on titles and tenure are struggling to keep up, and how the next generation of workers may leapfrog traditional career ladders entirely. It’s a conversation about compensation on the surface, but underneath it’s really about power: who gets heard, who creates leverage, and who gets left behind when organizations flatten faster than expected.Related Links:Join the People Managing People CommunitySubscribe to the newsletter to get our latest articles and podcastsConnect with Kyle on LinkedInVisit Sequoia Consulting GroupSupport the show