Jeremy Wilson
Head of Engineering at Lendal Pro Technologies Inc
Based in United States
Summary
VP / Head of Engineering | Flat Player-Coach Orgs at Scale | AI-Native Engineering Orgs | Board & M&A Diligence | Healthcare & Fintech
About
I build the engineering organization that builds the product. Seventeen years in engineering, fifteen leading organizations of eight or more. Most recently an agentic AI trading platform shipped in 90 days with 6 engineers; before that scaling WebPT from 2 to 60+ through the Battery Ventures growth investment.
I run flat, player coach orgs, and I ship code alongside the team in every role. At WebPT I built the developer platform - self-service DevOps, an ephemeral Docker dev stack, and configuration as code with Puppet. WebPT scaled 2 to 60+ across 8 Agile teams with tech leads rather than managers, plus one SDM/EM on team growth and performance. Lendal Pro and Chassi had no managers. Redirect Health ran flat with one Director and me, both in the codebase and shipping.
How I operate:- Flat, player coach orgs. WebPT tripled user story throughput over 6 months and made sprint and program delivery predictable while the org stayed flat.- Board and M&A diligence. Presented engineering strategy to the WebPT board quarterly. Led product and technology due diligence across seed and Series A rounds and for multiple acquisitions.- AI-native engineering org design. Lendal Pro ran agentic development, AI code review, automated testing, and infrastructure-as-code as the primary delivery practice, shipping a global trading product with 6 engineers.- Agentic platform architecture. A graph-based agentic orchestrator running playbooks as loss-function loops, with deterministic services as the hard backstop and the LLM layer producing probabilistic decisions. Loss function design so the loop can tell whether it is getting closer, and held out grading so hallucinations get caught before a customer sees one.- Global delivery org design. 37 outsourced engineers across Mexico, India, and Costa Rica, integrated as core product engineering.
Recent outcomes:- WebPT (2009-2016): 2 to 60+ engineers in a flat tech-lead org; HIPAA-compliant ISO-27001-certified platform for 10,000+ clinics; 20 Mexico outsource engineers.- Redirect Health (CTO, 2021-2023): 15-person org redesign; data platform modernization; uptime 95% to 99.9%; 3x customer growth; 9 India outsource engineers.- Lendal Pro (2023-2026): agentic AI trading platform across 2 DEX and 9 CEX on 3 continents; Kubernetes across 3 regions.
What I'm looking for:A Director, VP Engineering, Head of Engineering, or CTO seat building the org and the platform together - flat or scaling into structure, AI-native delivery, and board and investor scope.
Reach me at antifragileer@gmail.com.
Skills
Software Architecture, Cloud & Infrastructure, M&A / Due Diligence, Platform Modernisation, Cybersecurity, Engineering Leadership, Vendor Management, DevOps, Governance & Risk, Data & AI
Regions covered
Industry experience
Fintech, SaaS, Healthcare
At a glance
Jeremy brings hands-on experience across Software Architecture, Cloud & Infrastructure, M&A / Due Diligence, Platform Modernisation, Cybersecurity, Engineering Leadership and 4 other areas. Available for engagements across Europe, North America, South America. Industry experience includes Fintech, SaaS, Healthcare.
How fractional CTO engagements with Jeremy work
Jeremy works on a fractional basis — typically one to three days a week for an agreed engagement length — so you get senior technical leadership without the cost or commitment of a full-time hire. Engagements commonly include technical due diligence, board reporting, engineering team leadership, technology strategy, architecture reviews, hiring support, and stepping in as interim CTO during a transition.