Episode
Shawn Yeager - AI and the Billable Hour
- Podcast
- Ditching Hourly
- Published
- Jun 6, 2026
- Duration seconds
- 2588
- Processing state
not_requested- Canonical source
- https://share.transistor.fm/s/7dc8db2d
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Summary
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 - Introduction 01:54 - AI and the billable hour 03:56 - The judgment sandwich 05:19 - Strategy, execution, and hidden value 09:06 - Client conversations about AI pressure 13:26 - Validating AI output 15:29 - Judgment, marketing, and cost of being wrong 17:07 - AI transformation and commercialization 20:08 - The hard parts big firms still need humans for 22:20 - Cost recovery versus new offerings 25:35 - Agents as extra employees 26:40 - Interns versus chiefs of staff 28:44 - Scaffolding agent workflows 30:12 - From chatbots to delegated workflows 37:00 - AI adoption inside firms 42:01 - Closing remarks Shawn 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 . (00:00) - Introduction (01:54) - AI and the billable hour (03:56) - The judgment sandwich (05:19) - Strategy, execution, and hidden value (09:06) - Client conversations about AI pressure (13:26) - Validating AI output (15:29) - Judgment, marketing, and cost of being wrong (17:07) - AI transformation and commercialization (20:08)…