Operations11 min
The Invisible Dependency
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.
Read the story →
STORIES, FIELD GUIDES AND PLAYBOOKS FOR B2B PRODUCT LEADERS
The operating manual I wish I'd had for complex platforms
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 →FIELD GUIDES
Every complex industry runs on the same primitives.
I decompose them in public, one industry at a time, so you can learn any domain faster. Each guide maps the same ten primitives, then covers what doesn't transfer: the money, the power and the cost of being wrong.
Browse the Field Guides →AI agents: orchestration platformsThe 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.B2B payments: cross-border payoutsMoney leaving a US or Canadian business for workers, contractors and suppliers abroad: how FX, payout rails and settlement work, how global payroll runs, what each route really costs, and who pays when a payout arrives late, short or not at all.B2B payments: order to cashMoney coming in: how a US or Canadian seller turns an order into cash. Credit and terms, invoicing, the rails payers use, cash application, collections and deductions, what each step costs the seller, and who pays when it goes wrong.B2B payments: procure to payMoney going out: how US and Canadian businesses approve and pay their suppliers, why accounts payable is a control function first, what each rail costs the buyer and earns it, how supplier-impersonation fraud works, and who pays when it goes wrong.B2B payments: spend managementMoney going out through employees: corporate cards, expenses and reimbursements in the US and Canada, how a fintech card program is built, what each instrument costs and earns, and who pays when a card is misused or a receipt never arrives.Telco: numbers and sendersHow a business gets a number or sender approved, provisioned and delivered across SMS, RCS, WhatsApp and voice in the US, Canada and beyond, who can say no along the way, and who pays when it fails.
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
Situations I'm still writing my way through
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).
- 47In progressOperations
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.
- 24QueuedOperations
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.
- 11QueuedPlatform Modernization
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.
- 8QueuedPlatform Modernization
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.
- 4QueuedLeadership
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.
- 3QueuedMetrics
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.