Getting Here

IBM

I got my feet wet in the basement caverns of IBM Bromont’s IT department.

This was pre-Y2K, when a surprising amount of the world’s anxiety was wrapped up in how software handled dates. I spent time around infrastructure, support, Windows NT migrations, batch files, and automation. The first time I saw a repetitive task disappear behind a script, something clicked.

Computers were not just tools for doing work. They were tools for removing work.

That idea stuck.

Belmont Web Services

From there, I found my way into online products at Belmont Web Services, a company that no longer exists but left a mark on how I think about online systems, subscriptions, and growth.

It was the early recurring-membership era, and the platform was doing real volume. I started as an integrator, but the work quickly pulled me deeper into automation, Perl, registrations, lifetime value, PPC bidding, SEO, and the early mechanics of internet growth.

This was the AltaVista era, before Google had eaten the world. Search, performance, content, payments, and conversion were all tangled together, and the feedback loops were immediate. You changed something, and the numbers moved.

Fetch The Web

In 2004, I started my own consulting company, Fetch The Web. Most of the work sat somewhere between affiliate marketing, SEO, SEM, and custom web development.

One of the more painful and memorable projects was a mobile-first social network built around WAP and WML. It was 2005, the tooling was brutal, and “mobile-first” meant something very different than it does now.

It was also a good reminder that technology shifts rarely arrive fully formed. You usually meet them when they are awkward, limited, and frustrating.

4th Whale

At Ex-situ, later 4th Whale, I started in SEM and PPC automation and got pulled into product and platform work. The company had acquired a LAMP-based stack while most of the organization was still rooted in classic ASP. I became the first LAMP developer, then the fixer, then the lead, and eventually CTO.

We moved through multiple generations of stack decisions, from ASP and .NET to LAMP, React, Express, and eventually Next.js. We scaled the team, added product and UX disciplines, implemented OKRs, and built a repeatable way to bring acquired properties onto our infrastructure.

That period taught me that technical leadership is rarely about the perfect architecture diagram. Most of the job is creating enough clarity that people can make good decisions without you standing over their shoulder.

MavTek

At MavTek, the problems got bigger and more interesting. I started with the live streaming division during a large platform rewrite built around event-driven services, microservice backends, and micro frontends. The architecture was modern, but the lesson was familiar: modern technology does not automatically create customer value.

Teams still need focus, sequencing, and a short path between the work and the outcome.

Within 90 days, I had moved to the flagship ecommerce division, where the scale and business impact were impossible to ignore. Product performance, client-side speed, conversion, reliability, and delivery frequency all mattered because they showed up in revenue.

We introduced clearer product KPIs, lead and lag measures, better reporting, leaner delivery practices, and a stronger connection between engineering decisions and product outcomes.

I also learned how much damage “deadline mode” can do when teams forget why the work exists in the first place.

Eventually, I took on broader engineering responsibilities, starting with the web layer and eventually all of product development. The work encompassed incident management, quality systems, SaaS spend, cloud cost controls, budget visibility, delivery metrics, and team structure.

None of that sounds glamorous, but it is the operating system underneath product development. If that system is weak, every roadmap eventually pays the price.

Revaly

Then came Revaly.

I joined as VP of Engineering when the company was still FlexPay. It was a Microsoft shop with a lot of legacy gravity: older .NET, manual deployment practices, heavy compliance rituals, centralized decision-making, and a feature-factory muscle memory that had built up over years. The previous technology leadership had been deeply involved in nearly every decision, which meant the team had to relearn ownership.

The first chapter has been culture and governance. We revamped compliance and security programs, automated more of the vulnerability and monitoring work, reduced audit drag, and started making technical risk visible in a way the business could understand. We split a centralized team into more stream-aligned product teams and moved more decision-making closer to the people doing the work.

The second chapter has been delivery. We adopted DORA metrics, attacked pipeline debt, reduced lead time for change, and started shifting the release mindset from ceremony to flow. The goal was not “move fast” as a slogan. The goal was to shorten feedback loops so the team could learn faster and operate with more confidence.

The third chapter is product.

I took on Product, and we unified Product and Engineering into Product Development. That changed the work. The questions became less about what we could ship and more about what outcomes we are trying to create. We reworked the product lifecycle around briefs, PRDs, build, launch, operate, measure, and sunset. We pushed harder on leading indicators. We use AI as a development multiplier, not as a novelty. And we are repositioning the company from reactive payment recovery toward proactive approval optimization.

That work is becoming Revaly’s Trust Network: a way to improve authorization outcomes by creating better trust and data exchange between merchants, fraud detection platforms, orchestrators, and financial institutions.

The Thread

In hindsight, that thread has been there since the beginning.

At IBM, it was automation.

At Belmont Web Services, it was performance and conversion.

At Fetch The Web, it was figuring out how new channels worked before they were mature.

At 4th Whale, it was turning messy platforms and acquisitions into repeatable systems.

At MavTek, it was connecting product development to revenue, speed, reliability, and customer experience.

At Revaly, it is about turning payments, data, trust, product strategy, and engineering execution into one coherent system.

I have never been especially interested in technology for its own sake. I like technology when it changes the shape of what is possible. I like product work when it is close enough to the customer that the feedback is uncomfortable and useful. I like engineering leadership when it creates teams that understand the business, own the outcome, and do not need permission for every good decision.

That is the journey so far: from basement IT work and batch files to product development, payment optimization, trust networks, and AI-enabled execution.

Still the same basic question, though:

What are we trying to make better, and what is the simplest useful thing we can do next?