STORIES, FIELD GUIDES AND PLAYBOOKS FOR B2B PRODUCT LEADERS
Every regulated, partner-heavy B2B industry runs on the same ten primitives. The Field Guides map them industry by industry, the Playbooks turn them into decisions with checklists, and the Stories show what happened when I made those calls for real.
No right answers. Only the ones I picked.
13+ years building B2B products, making calls under uncertainty, and learning what "owning it" means. I owned a nine-figure ARR product portfolio at Twilio, a corporate venture P&L as GM, founded a VC-backed automation startup, and scaled cross-functional orgs across 10+ countries and timezones. Same instincts. New decisions and blind spots every time.
Who is writing this →I just joined a new company
Earn trust, learn the domain and set direction in 60 days.
I need to learn an industry fast
The main players and ten primitives, one industry at a time.
We just acquired a platform
Decide what to kill, keep, migrate or share, and in what order.
We're going AI native
Change how the team ships, works and serves customers, and prove it.
Field Guide · October 2026
Who a platform must verify before a business can move money, how KYB, KYC and ongoing monitoring work, why your sponsor bank or card network sets the real bar, and who pays when a fake company, a deepfake or a missed alert gets through.
Field Guide · October 2026
The layer that runs AI agents in production: orchestration and control, context and memory, secure tools, evals and governance. What it costs, what breaks, and who is accountable when an agent acts.
Playbook · October 2026
For a product leader asked to make a regulated platform team AI native: measure first, then change how code ships, how internal work is reviewed and what customers see, in that order, with outcome metrics, real oversight and partner sign-off.
Playbook · October 2026
What to do with the products after you buy a platform company: sort every product and component into kill, keep independent, migrate or shared services, sequence the work, keep customers and revenue, and clear the licences, banks and registrations that slow regulated deals.
Story · August 2026
I told GTM we were almost ready to launch. Nothing standing between us and Japan. Then the production test failed, and introduced us to the invisible dependency.
There is a problem you're facing and would like some input.
Send me a real situation, not the abstraction. I answer most messages within a week.
Send me a message →Backlog
These are the pieces in progress. These are unwritten. Vote for the one you want next and I'll move it up the queue (I write in that order).
A client's traffic spike took down our service, but not the API
The API had 100% uptime, but the service was still down. What a silent single point of failure actually costs. Nobody designed for this failure, and every client paid for it.
The API they asked for, and never turned on
Customers asked it for years. When we shipped it, adopting it meant rewriting their internal process, and investing their engineering time. Wanting automation is not the same to be ready to pay for the switch.
The compressed roadmap. Modernizing after a Sev0.
We'd staged a ten-month modernization plan with the dependencies mapped in order. A Sev0 outage erased the sequence overnight. Leadership wanted visible progress in weeks, not a plan.
The uphill battle to fund platform modernization
Every planning cycle, modernization scored highest on important and lowest on urgent. Quarter after quarter, until we ran out of runway to keep deferring it.
The Peer-to-Boss Jump
I got the promotion I wanted. Last week I was in the standup as one of them. Now I run it. They already trusted me, that was never the question. The question was whether I trusted myself.
The accidental org chart
The lines between my sub-teams had formed organically over time, never by design. Redrawing them now might cost us months of delivery.