About

I've spent thirty years as the chief architect for whatever is new — infrastructure services on one side, customer and company solutions on the other. Web hosting in 1994. Enterprise cloud in 2008. DevOps in 2014. AI now. The pattern is always the same: a powerful new platform shows up, everyone builds demos, and someone has to design the system — and the delivery plan — that makes it real. That's usually been me.

As I've gotten more senior, the seat has evolved into CTO roles. What hasn't changed: I still write code — more than ever now that I build solo — and I still spend the other half of the week advising leadership and program teams.

I'm based in Los Angeles, originally from the UK. CISSP. Today I run a Fractional CTO practice through Mode2 — my own company, and these days a deliberately solo vehicle — working with 2–3 companies at a time on AI strategy, enterprise architecture, and the technology decisions that determine whether you scale or stall. Alongside that, I design, build, and run my own AI systems in production.

Selected work

The throughline across thirty years: be the chief architect for whatever platform is new, design the system and the delivery plan, and stay through delivery. A few things I'm proud of —

  • Brought AWS into the enterprise early. Introduced AWS to General Motors in 2008 and trained 100+ of their architects on cloud; built Capgemini's cloud practice from scratch and made them the first Systems Integrator to partner with AWS — a milestone their CEO acknowledged publicly.
  • Built Amazon's Western US Professional Services org from zero. After running professional services at RightScale (AWS's largest consulting partner at the time), Amazon recruited me to build the org — 80+ people, clients including Adobe, Apple, Boeing, and Intuit, and AWS's first million-dollar consulting engagement.
  • Founded and exited a DevOps consultancy. Co-founded DualSpark in 2014, scaled to 35 engineers in nine months, ran transformations for Nike, Experian, FICO, 23andMe, and VSCO, and exited to Datapipe in fourteen months.
  • Operated at enterprise scale. Chief Enterprise Architect at Capgemini on GM's $2B IT in-sourcing (team of 50); ran a $100M professional services organization at Rackspace (540 engineers across the Americas); CTO at Redapt across AWS, generative AI, and security platforms.

The arc runs from building one of the UK's first commercial web hosting platforms at IBM in 1994 to running AI agents in production today — web, cloud, DevOps, AI, the same pattern each time. The full history lives on LinkedIn; how I work with clients now is on the services page.

What I'm building

When I'm not working with clients, I build and run my own AI systems in production:

  • Sterling — a sovereign, local-first advisory trading agent. Proposes, briefs, and alerts; never places an order.
  • Markdown — a free, open-source markdown editor for iOS.

Earlier experiments — ClawHQ and AIShore — are retired but documented on the projects page, because the journey is part of the record.

Get in touch

If you're working through a technology decision where the cost of getting it wrong is high — AI adoption, architecture strategy, build-vs-buy, team structure — that's the conversation I want to have.

website@simonplant.com ·LinkedIn

Colophon

This site is built with Astro and Tailwind CSS. No JavaScript frameworks — every page is static HTML and CSS. Typography is Literata for prose, DM Serif Display for headings, JetBrains Mono for code. Dark mode only.