June 5, 2026
Shawn Yeager - AI and the Billable Hour
Emerging technology advisor Shawn Yeager joined me on Ditching Hourly to talk about what professional services firms can sell after AI.
Chapters
- AI and the billable hour
- The “Judgment Sandwich”
- Strategy, execution, and hidden value
- Client conversations about AI pressure
- Validating AI output
- Judgment, marketing, and cost of being wrong
- AI transformation and commercialization
- The hard parts big firms still need humans for
- Cost recovery versus new offerings
- Agents as extra employees
- Interns versus chiefs of staff
- Scaffolding agent workflows
- From chatbots to delegated workflows
- AI adoption inside firms
Guest’s Bio
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.
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Yours,
—J