Shawn Yeager - AI and the Billable Hour

Founder of Upshift, Shawn Yeager, joined me on Ditching Hourly to talk about how AI is killing the billable hour and what professional services firms can do about it. Jonathan and Shawn dig into judgment versus execution, what firms should commercialize after AI, why cost-cutting is only the first move, and how agent workflows change what small and midsize firms can do.00:00 - Introduction01:54 - AI and the billable hour03:56 - The judgment sandwich05:19 - Strategy, execution, and hidden value09:06 - Client conversations about AI pressure13:26 - Validating AI output15:29 - Judgment, marketing, and cost of being wrong17:07 - AI transformation and commercialization20:08 - The hard parts big firms still need humans for22:20 - Cost recovery versus new offerings25:35 - Agents as extra employees26:40 - Interns versus chiefs of staff28:44 - Scaffolding agent workflows30:12 - From chatbots to delegated workflows37:00 - AI adoption inside firms42:01 - Closing remarksShawn Yeager runs Upshift, a firm focused on helping professional services firms understand what they sell after AI. His career has focused on emerging technology and getting it to market, including work on Microsoft's first browser team, the SaaS/cloud wave, mobile, Bitcoin, and AI. His background is in computer science, and his work has included sales, marketing, partnerships, consulting, Accenture, early-stage startups, and his own ventures. Learn more at upshiftco.com. ----Do you know you need to niche down, but keep hesitating because you're afraid of picking the wrong niche, cutting off good opportunities, or boxing yourself in?You DON'T need more convincing that vague positioning is a problem.You DO need a way to make positioning feel less risky so you can finally choose a direction, test it in the market, and adjust without blowing up your business.On Tuesday, September 8th, 2026, at noon Eastern Time, I'm running a live workshop called Positioning For Soloists Having A Hard Time Niching Down.That's what we'll tackle in this workshop.It's the second session of my Fall 2026 Soloist Growth Workshop series for expertise-based business owners just like you.Live attendance is limited to 20, so don't wait.Learn more at: https://jonathanstark.com/sgsEnroll in Positioning For Soloists now »Hope to see you live in Zoom on Tuesday.