"Freed capacity is not value in itself; it is a leadership decision waiting to be made." — with Cindy Chastain, former Mastercard executive
Cindy Chastain
Executive Advisor; former SVP, Customer Experience & Design, Mastercard
Successful AI transformation requires enterprise observability — a clear picture of how work actually flows — paired with a disciplined cadence to baseline, intervene, measure, and harvest value into P&L impact.
Uber exhausted its annual AI coding budget four months into the year. As subsidized pricing ends, CFOs need workflow-level cost visibility and value attribution — not adoption leaderboards.
Parable tested context graphs against 1,400+ enterprise tasks on the APEX-Agents benchmark. The gap wasn't reasoning — it was navigation. Agents with queryable organizational context completed tasks nearly 2x faster with 64% fewer resources.
A system of understanding is necessary for a human + agent enterprise workforce.
On Time & Work: Allison Pickens on her path from writing and consulting to SaaS and AI investing, and how her view of time has evolved.
On Time & Work: Jair Clarke on his journey from the streets of Miami to entrepreneurship, and the lessons he’s learned about time, money, and purpose.
On Time & Work: Dave Heath on his evolving relationship between time, work, and leadership — and how obsessing over small details drives big impact.
Adam Schwartz joins Jeff Rudner on the 5 to 50 podcast to talk about growing TeePublic to $130M, how AI is transforming workplace efficiency, and aligning attention with intention.
Adam Schwartz sits down with investor Allison Pickens to discuss why time is a company’s most precious resource — and how to align collective time with strategy at scale.
One CEO learned only 28% of his team’s time went to planned work. The other 72% was “Unplanned Work” — and it’s invisible until it’s too expensive to ignore.
We interviewed over 100 C-Suite leaders about their most valuable asset — time — and found it is still invisible. Introducing the P&L of company time.
Founder Mode unlocks speed, and the missing leverage is context. How to keep founder-level context as you scale past Dunbar’s number.
