Jean-Christophe Roux

TOFF SYSTEMS

Fractional CTO — I build tech organizations that make the most of AI

jcroux@toffsystems.com (819) 421-3065 LinkedIn

Who I Am

I build technology organizations that make the most of AI — teams, tooling, and ways of working designed around what AI can actually do today.

I've spent 25 years building software and 10 years leading technical teams. I've rebuilt how teams design, ship, and operate software with agentic tools — and the result is production systems delivered by a fraction of the usual headcount. Now I work as a fractional CTO and advisor, embedded with startups, incubators, and investors who need that done for them.

When you work with Toff Systems, you work with me directly. No account managers, no junior associates handed your project. That's the point.

What I Do

AI-Native Tech Organizations

I don't just advise on AI — I build with it, and I build teams around it. I reshape how an engineering organization works with agentic coding tools and LLM-powered automation: what to build, what to buy, how to ship, and what the team needs to look like when AI does a large share of the work. The outcome is a smaller, faster tech organization that puts real systems in production — not demos.

Fractional & Interim CTO

I step into the technical leadership role for companies that aren't ready for a full-time CTO — or need experienced cover during a transition. I make architecture decisions, manage development teams, and represent the technical side to boards and investors.

Technical Due Diligence

I advise VC firms and investment committees evaluating software companies. I assess codebases, infrastructure, team capabilities, and technical debt — and translate what I find into investment risk.

Investment & Board Advisory

I advise venture capital funds, investment committees, and boards on technical strategy, portfolio company support, and technology-driven business decisions. I translate technical complexity into investment risk and opportunity.

Recent Work

Marketplace platform

AI-enabled business transformation

A booking platform was hitting a ceiling: manual curation couldn't scale beyond a handful of daily transactions. I designed an AI-powered matching system using video analysis and algorithmic recommendations that fundamentally changed the sales model — enabling the business to scale from 5 bookings to 100+ daily without proportional headcount. The technology didn't just automate a process; it transformed how the business operates.

SaaS platform

Infrastructure optimization

Conducted infrastructure audit identifying unnecessary complexity in a legacy AWS setup. Proposed migration path projecting 60%+ reduction in cloud spend while improving deployment reliability. Sometimes the win isn't new technology — it's removing what shouldn't be there.

Startup incubator

CTO in residence

Ongoing engagement as technical advisor to an incubator: delivering lectures and workshops on AI and product development, serving on the selection committee for new cohorts, and providing hands-on technical consulting to portfolio companies navigating early architecture decisions.

Investment committee

Technical due diligence

Conducted code and architecture review for seed-stage B2B software acquisition. Identified critical technical debt and team capability gaps that materially affected deal structure and valuation.

How I Work

Advisory

Ongoing strategic guidance with regular check-ins. A sounding board for technical decisions, available when you need senior judgment on questions large and small.

Embedded Leadership

Part-time or interim executive role with direct involvement. I join your team to drive specific initiatives, make architecture decisions, and fill leadership gaps — whether you're a startup building your first technical team or an established company navigating a transformation, post-acquisition integration, or strategic technology initiative. Minimum 3-month engagement.

Project-Based

Defined scope for specific challenges: due diligence reports, architecture reviews, AI feasibility assessments, or building a new capability from scratch. Fixed timeline and deliverable.

Background

I've built products from scratch, inherited legacy systems, scaled teams, and shut down projects that should never have started. My background combines deep technical experience with business strategy — I can talk to your board about market positioning and debug your deployment pipeline in the same week.

Before consulting, I held senior technical leadership roles across companies from bootstrapped startups to established enterprises. I've been a founder, raised capital, and learned the hard lessons that come with building ventures.

Based in Quebec. I work in English and French.

Get in Touch

If you're a founder who wants a tech organization built around AI, an incubator looking for a CTO in residence, or an investor who needs technical diligence — let's talk.

If you're a company seeking interim technical leadership for a strategic initiative, or a recruiter with a mandate to fill — I'm open to conversations.

jcroux@toffsystems.com (819) 421-3065 LinkedIn