Your AI Strategy Doesn't Need a Task Force. It Needs a Home.
Why most enterprise AI initiatives stall — and the organizational design pattern that keeps them moving.
Jeff Sheldon
Engineering executive. AI strategist.
Builder of platforms at scale.
25 years leading engineering organizations across SaaS, fintech, and consumer tech — from bootstrap startups to platforms processing $15B+ annually.
About
I've spent 25 years building and scaling technology organizations — from co-founding a bootstrap services company with operations in California and China, to leading engineering through Recurly's growth from sub-$30M to $100M+ in revenue as a senior technology leader.
Today I set enterprise AI strategy and technical direction at Recurly. I led technical due diligence on two 2025 acquisitions, brief the board on technology and AI posture, and personally close enterprise accounts with organizations including the NFL, Alaska Airlines, and Experian.
I'm drawn to roles where the CTO must bridge engineering with go-to-market and corporate development — and where AI direction needs to come from someone who has shipped under compliance constraints, not theorized about it.
25+
Years in Tech
$15B+
Annual Payment Volume
100+
Engineers Led
99.99%
Platform Availability
Career
Chief Architect — Recurly
2024 – Present
Senior-most technology executive beneath the CTO. Set enterprise AI strategy, led technical due diligence on two acquisitions (Prive and Redfast), and personally closed enterprise deals with the NFL, Alaska Airlines, and Experian. Sponsored Recurly Compass, an AI-powered product recognized with four Stevie Awards.
SVP Engineering — Recurly
2020 – 2024
Owned all of engineering through growth from sub-$30M to $100M+ in revenue. Sustained 99.99%+ availability on a PCI Level 1 platform processing $15B+ annually. Scaled engineering to 100+ across multiple geographies, managing ~$16M R&D and ~$7M infrastructure budgets.
VP Engineering & Architecture — Recurly
2015 – 2020
Led the zero-downtime migration from data center to Google Cloud on Kubernetes, featured by Google Cloud as a reference fintech customer. Built the platform engineering function and incident response program that enabled sustained four-nines availability.
Engineering Leadership — Life360, StumbleUpon, Coupa
2011 – 2015
Scaled Life360 engineering from 15 to 60+ during hypergrowth. Led mobile engineering at StumbleUpon for apps featured by all major app stores. Drove quality improvements across multi-continent teams at Coupa Software.
President & CEO — Infuze Technologies
2008 – 2009
Co-founded and ran a bootstrap services company delivering software development across California and China. Grew from 3 to 20 employees in the first year.
Engineering Manager — MICROS-Retail (now Oracle Retail)
2001 – 2008
Progressed from R&D engineer to engineering manager building Datavantage XStore. Established and operated a 40+ person offshore development center in China — foundational experience for leading global teams throughout my career.
B.S., Computer Science — Heidelberg University, Tiffin, OH