Montreal-made and in its transformation era: This is Lightspeed, 20 years later

Dax Dasilva was 28 at the time, living above what would become his first office in a third-floor Village walk-up. Coding through the night on a Mac—fuelled by cheap coffee and whatever creative force it is that makes Montrealers keep making things long after everyone else has gone to bed—this was where Lightspeed’s billion-dollar platform  quietly began to take shape.

“I’d write code until four in the morning,” he says, “then walk down the back steps to where the team was just starting their day.”

This wasn’t Silicon Valley hustle culture. It was something scrappier and far more local, a startup story told not in pitch decks and VC buzzwords, but in cheap coffee and second-hand furniture.

As “more of a designer than a programmer,” Dax remembers how Lightspeed wasn’t built as a piece of enterprise software, but as something you’d actually want to use. Something that made sense. Something that gave shopkeepers, restaurateurs, and independents the feeling that they were in control.

All of this was in 2005. Apple was having its comeback moment, and Dax saw a gap: beautiful machines, but nothing for the businesses that actually used them. So, he built a point-of-sale system that looked and felt like iTunes, only for inventory, invoicing, and analytics.

“There wasn’t really any business software on Mac,” he says. “People wanted to feel in control of their technology. That’s what we gave them.” 

Designing for control

The retail landscape in 2005 was cluttered with clunky systems—expensive to install, difficult to understand, and completely indifferent to the actual needs of the people using them.

“It was like a black box,” Dax says. “You’d put data in and get a report out for your accountant, but it didn’t help you understand your business.”

Lightspeed flipped that: It let business owners actually see what was happening—what was selling, what wasn’t, what to restock, how their stores were performing. It turned inventory into something dynamic. POS became less of just a transaction processor, and more of a dashboard for running your livelihood.

Even in those early years, the product had legs. Dax didn’t take any outside investment for seven years, scaling to $10 million in annual revenue before ever bringing on VCs.

“The product really sold itself,” he says. “People saw it and immediately wanted to run their store with it.”

Montreal in the code

There’s something fitting about Lightspeed being born in Montreal. The city has always blurred the line between commerce and culture, between selling something and making something: Fashion, food, music, retail, restaurants—each one has deep roots in this city, and Lightspeed grew up with all of them.

The city’s influence runs deep: in the focus on user experience, in the multicultural, multilingual workforce, in the commitment to independent businesses that give neighbourhoods their character.

Even the company’s original design language bears the city’s mark—clear, confident, quietly stylish:

“You can find Montreal’s influence in the original versions of Lightspeed that I built for sure, and it’s always a big part of our DNA—the design DNA, but also all the cultural DNA,” Dax says.

That sensibility continues to guide how Lightspeed builds today. Whether it’s adapting workflows to European tipping culture, integrating blockchain-inspired compliance tools, or creating tools to track social ROI, the company treats technology not just as a utility, but as an extension of human behaviour.

It’s this constant, future-ready state of being—a sense of adaptability rooted in Lightspeed’s culture—that’s as defining for the company as any product feature, and it can be seen in something any Montrealer can relate to: Moving.

From the walk-up in the Village, Lightspeed eventually moved into a string of bigger and more interesting spaces. Today, the company’s headquarters is known as ‘the castle’, a sprawling restoration of the old Gare Viger building just a few blocks from City Hall.

“It’s walking distance from where we started,” Dax says. “We’ve created our own crossroads for a company now found in more than 100 countries.”

From retail to restaurant to runway

Lightspeed didn’t stay in one lane for long. After tackling retail, the company expanded into hospitality—serving restaurants, resorts, and golf courses. What remained constant was their philosophy: simplify the complex, give owners control, let people focus on their passion instead of back-office drudgery.

“We took that philosophy, our philosophy, and brought it to hospitality,” Dax says. “It’s more than a point of sale. It’s the central nervous system, the brain behind any given business.”

Today, Lightspeed operates less like a single tool and more like a lightweight operating system for ambitious businesses, the kind that outgrows plug-and-play solutions without wanting the sprawl of a full enterprise stack. What started with a point-of-sale has stretched into embedded payments, loyalty systems, supplier connections, capital financing, marketing, and, increasingly, AI-driven insights—all woven into one platform built to let owners run smarter, move faster, and reclaim time.

The complexity of running a modern retail or hospitality business hasn’t gone away. But Lightspeed’s job, as ever, is to make it feel simple again. 

“The landscape has gotten way more complicated,” Dax adds. “You’re expected to be everywhere at once—digital, mobile, social, delivery. And you still have the same number of hours in a day.”

It’s new territory for Lightspeed, but it’s out there now, building AI and automation into the platform—not just to cut down admin work, but to rewire how businesses source, pay, and grow. Tools like NuORDER are changing how retailers manage suppliers and inventory, while embedded finance is helping merchants access capital faster and more easily than traditional banks ever could. The goal isn’t just efficiency; it’s freedom: giving owners the ability to move faster, think bigger, and stay focused on what actually fuels them.

Tech that feels like a person

Ask Dax what makes him proudest, and he doesn’t cite product features or market share. He talks about customers who opened a second or third location because they finally had a system that made it feel possible. Or the ones who took their first real vacation in years because they could monitor their stores from their phones.

“I’ve heard people say Lightspeed gave them the ability to scale—and the freedom to step back,” he says. “That’s real success.”

He talks about his employees, too—the ones who joined when the company was small, and now lead entire teams. About being gay, being a person of colour, an advocate for LGBTQ rights as a founder, and how that shaped the company’s culture from the start. “Before DEI was a thing, we were already living it. People bring their full selves to work here. That’s one of the most important things.”

Every year, Dax rewrites his job description. “I ask myself: what does the company need from me now? Sometimes it’s something I have zero background in. But if I don’t take it on, no one will. That’s how we grow.”

So what’s next? In a word: focus.

Looking forward 20 years

On the retail side, Lightspeed is doubling down on its North American footprint. In hospitality, Europe remains the fastest-growing market. The company’s NuORDER tool is expanding how businesses source, finance, and manage inventory—something especially crucial as global supply chains get more unpredictable.

“We’re thinking ahead to what our customers are going to need,” Dax says. “And supply is a big one. The right products, at the right cost, at the right moment—that’s make or break.”

The company is entering what Dax calls its “transformation era”, a shift from growth at all costs to sustainable, profitable growth rooted in long-term merchant value. That means fewer disconnected tools and more vertical integration; fewer distractions, more focus.

AI is central to this next phase—not as a shiny add-on, but built into the core experience as a time-saving engine.

“Nobody gets into retail or restaurants because they love admin. They get into it because they love bikes. Or Spanish food. Or beautiful things,” Dax says. “We want to give them that time back.”

That means building tools that don’t just support operations but help reimagine them—AI that anticipates instead of reacts, supply chains that think like shopkeepers, and platforms that act more like business partners than software suites.

It’s not about adding complexity for complexity’s sake. Lightspeed’s future is about a tighter, more unified system built to anticipate what merchants need before they even ask: helping them manage supply chains, make smarter decisions faster, and scale without burning out.

Even as technology grows more sophisticated, Lightspeed hasn’t lost sight of a simpler truth: shopping and dining are still entertainment. They’re how people unwind, explore, express themselves. And Lightspeed’s job is to make sure those moments are delightful, efficient, and repeatable, even when the staff is new and the shelves are in flux.

What’s more, Lightspeed is still built around the same premise it started with in that walk-up apartment: give people the tools to run better businesses—and get back to doing what they love.

It’s grown up, sure, but it hasn’t grown out of itself.

“Montreal gave us the space to become who we are,” Dax says. “And now we get to help other businesses do the same. That’s what it’s always been about.”

From the Village to the castle, from Mac dealership POS to global commerce platform, Lightspeed has spent the past 20 years helping define what retail and hospitality tech can look like. 

The next 20? They’ll be about scale, intelligence, and reclaiming time: AI that anticipates instead of reacts, supply chains that think like shopkeepers, tools that think alongside you and not just for you, and businesses that thrive not because of what Lightspeed does for them, but what it makes possible. 

That’s the future they’re building toward one transaction, one table, one idea at a time.