Writing, frameworks, and tools on the commercial architecture of fintech, digital assets, and AI-native GTM.
Five layers. Four stages. What to install, what to skip, and what breaks when you buy ahead of your stage.
The founder motion and the repeatable motion are different skills. Most companies confuse the handoff and pay for it.
Build, partner, or adopt: the strategic choice every fintech now faces, and why most are choosing wrong.
Sales and product don't usually break all at once. They drift. Read the swing, restore the rhythm.
A GTM intelligence and orchestration system. Researches target accounts, synthesizes signals into a narrative diagnosis, drafts personalized outbound for human review, and connects directly into HubSpot, Gmail, and Slack. Built first for Pleasant Street's own outbound.
A B2B platform that turns static sales PDFs into AI-guided prospect experiences with buyer intent capture. DocSend tells you what they saw. Slate tells you what they thought. Live at sendslate.co with early users.
I work on commercial architecture: how go-to-market gets designed before there's a repeatable motion, how operating systems need to change as a business scales, and how to manage the transitions where most companies stall.
Seven years at Flipside, a blockchain data platform, where I led GTM through the company's growth from $2M to $15M ARR and founded a $0-to-$2M advisory line. Nine years before that at SS&C Eze, working with hedge funds and asset managers on trading workflows, compliance, and the systems behind both.
Pleasant Street is where I share what I'm building, what I'm learning, and how I think.
If any of this lines up with what you're building, let's talk.
avi@pleasantstreet.co