Enterprise AI learnings from the field jacobbsinger.com Est. May 2026

Enterprise Learnings + Personal AI unlocks.

Currently GTM at a hyperscaler. Deploying AI solutions at scale. Follow along for those learnings + a monthly running log of personal building, automating, and shipping learnings with AI dev tools — in real time, in public, with all the mistakes left in.

In this issue

Notes from the build.

A decade between technology
and the teams who bring it to life.

I’m Jacob. I’ve been in SaaS & PaaS GTM for over a decade, from Series A startups to Hyperscalers. These days I’m mostly focused on the intersection of agents and cloud endpoints, partnering closely with executive teams to turn early ideas into real, implemented systems that scale.

Most of my time has been spent with large healthcare and financial services organizations, helping them navigate AI from early ideas all the way to systems running at enterprise scale.

Outside the day job, I’m a vibe coder. I use AI to automate parts of my own life, experiment with new ways of building, and ship small apps and web experiences (this site is one of them). The patterns I run into: agents, cloud endpoints, where strategy meets working code, end up as my Musings.

This site is my attempt at a running log of that journey: what’s working, what’s not, and what it looks like to figure this out in real time.

Views expressed are explicitly that of my own.

Portrait of Jacob Singer

Get in touch.