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 - 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.
Creators and Guests
Host
Jonathan Stark
The Ditching Hourly Guy • For freelancers, consultants, and other experts who want to make more and work less w/o hiring
Guest
Shawn Yeager
Founder, Upshift · Advisor to frontier tech founders · 30 years commercializing what’s next
