Samuel Stephenson
Project Manager · AI & Operations Specialist
📍 Montreal, Quebec · 🇺🇸 Originally from Michigan
My Story
From tracking Iranian military communications 30,000 feet above ground to building AI systems that recover millions in lost revenue — my career has always been about one thing: finding signal in noise and turning it into action.
I spent six years in the US Air Force as an airborne intelligence analyst, flying combat missions and producing reports that reached national-level policymakers. The work demanded precision, speed, and the ability to synthesise complex, ambiguous information under pressure. It also gave me a deep respect for process — and for what happens when processes break down.
After the military, I transitioned into the tech sector and quickly found my footing in risk operations. At Hopper, I realised that the same analytical instincts I'd used to identify military patterns applied perfectly to fraud detection — I helped uncover a coordinated fraud ring and prevented over $200K in losses. At Super.com, I've taken that foundation and scaled it dramatically, growing our dispute operations from 4,500 to over 66,000 annual chargebacks while recovering $6.8M+ in revenue in 2025 alone.
Today I lead a team of analysts and manage complex cross-functional projects — from AI and RPA tool rollouts to OKR-driven initiatives — all while staying close to the data and the operational realities that make or break results. I live in Montreal with its mix of French and English, and I genuinely love the problem-solving culture of the city.
Career Timeline
Languages
What I Bring to Every Project
🎯 Precision
Six years of military intelligence work built an obsession with accuracy. I don't guess — I verify.
📊 Data Fluency
Comfortable in BigQuery, SQL, and Google Sheets. I build dashboards and tools that make data accessible to everyone on the team.
🤖 AI & Automation
Hands-on experience implementing Luminai, Automat, and AI-assisted dispute workflows at scale. I've seen what works and what doesn't.
🗣️ Communication
Four languages and a career bridging military, government, and startup environments means I can translate across teams fluently.
⚡ Speed to Value
Startup experience means I bias toward shipping. I build MVPs, measure them, and iterate — not the other way around.
📐 Structure
I bring Agile discipline to projects without the overhead. Clear OKRs, documented processes, and weekly momentum.
Core Values
Let's Connect
Whether you're looking to collaborate, hire, or just geek out about chargeback operations and AI — I'd love to hear from you.