When Canada Post stopped moving parcels, Gavin Thompson and his co-founder Kevin Bache had a very practical problem. Phoenix could have a working website, a recognisable brand and customers ready to use it. None of those things could carry a package to the front door. The founders integrated alternative delivery carriers overnight. The business had reached the point where a software decision could determine whether something physical arrived.
It is a useful opening scene for Thompson because it puts his work at the right scale. A national disruption becomes a set of connections that need replacing. A company promise becomes a delivery that still has to happen. The task carries none of the ceremony of a funding announcement. It does, however, have a deadline considerably less forgiving than a presentation calendar.
Thompson is Phoenix’s Toronto-based co-founder and co-CEO. His background is in software development, including work at MetaLab, TouchBistro and Apply Digital. The carrier episode brings those two descriptions together. He had become an executive whose company needed a response, and he remained an engineer capable of helping build one. For the customer waiting at home, the organisational chart was probably the least interesting part.
Other people’s products, then his own
Before Phoenix, Thompson developed products for businesses that included Walmart and Disney. Those names make an immediately legible introduction, but the more interesting part of his career is the movement between different kinds of product work. His experience spans Canadian technology companies as well as projects for large international brands. At Apply Digital, his background includes a senior software engineering role; at MetaLab, front-end development.
Those are jobs close to the point where an idea has to become usable. A screen can look convincing in a meeting and still leave a customer wondering where to click. A feature can work in isolation while behaving badly beside everything else. Building products means meeting those small failures one by one. Thompson’s career before Phoenix belongs to that practical world of making the thing work for someone else.
His education adds another thread: an associate’s degree in marketing at Camosun College, followed by a Bachelor of Arts in Science and Technology at York University. The subjects sit comfortably beside the later business, where technical work and reaching an audience both matter. The distinction between the disciplines becomes less tidy once someone has to persuade a customer to try the product they have helped build. A company eventually needs both skills in the same room.
Founding a company changes the ownership of the problem. There is no external client to receive the finished project and take responsibility for what comes next. The software, the customer relationship and the cost of keeping both alive become part of the same undertaking. Thompson brought an established technical career into that arrangement. Phoenix gave him a business in which the consequences of a product decision stayed close.
A company with two signatures
Phoenix was founded in 2019 by Thompson and Bache, and joined Y Combinator’s Winter 2021 batch. The partnership has continued with both founders serving as co-CEOs. That shared title is worth taking literally: this is a company whose public leadership has two names attached to it. A profile of Thompson therefore also has to make room for Bache.
Their backgrounds overlap in software, while bringing experience in marketing and design into the partnership. The overnight carrier integration was a joint effort. So was building the company that eventually attracted a new growth investor. It would be convenient to assign one founder all the machinery and the other all the persuasion. Their record offers a more intertwined picture, with building and selling connected in the same business.
Y Combinator supplied an international startup connection to a company focused on Canada. By 2025, the accelerator was investing again. For Thompson, that return gave the story continuity: the organisation associated with Phoenix’s early development was still participating at a later stage. The company had moved forward without changing the country at the centre of its ambitions.
The television in the room
Phoenix’s first national advertising campaign arrived during the Canadian Super Bowl broadcast on February 11, 2024. Created with Arrivals + Departures, its 60-second spot was called “Multiple Positions.” It staged a comic military predicament on a historic battlefield. For a business built around software, the choice of television was a reminder that customers do not spend their lives inside a founder’s preferred medium.
The campaign also made the division of work visible. Arrivals + Departures handled the television buy, while Phoenix’s own team took responsibility for performance marketing and social amplification. Director Rodrigo Garcia Saiz and production company FRANK Content helped turn the idea into a filmed advertisement. Thompson and Bache appeared in the campaign credits as the client’s founders and co-CEOs.
By February 2025, Phoenix was running its second Super Bowl advertisement. The repeat appearance matters more than the novelty of the first: television had become part of the company’s method. There is a pleasingly old-fashioned quality to a software business buying a place in the living room. The remote control remains an influential piece of consumer technology, even if it rarely receives an invitation to a startup conference.
Fifty million, carefully labelled
On March 13, 2025, Phoenix announced a CA$50 million financing round. Valspring Capital led the investment, Y Combinator returned, and CIBC Innovation Banking provided venture debt. The distinction between equity and debt belongs beside the number. The announcement described capital for the company’s next stage; it did not turn the headline amount into Thompson’s personal fortune.
The planned uses were concrete: expand the team, increase the visibility of the brand and scale operations. Each points to a different kind of work. Hiring adds colleagues who need direction. Advertising introduces people who will expect the service to function. Operational expansion has to absorb that attention. The financing connected these jobs financially, but the work of making them fit remained with the company.
At the time of the financing interview in March 2025, Phoenix had 35 people. Thompson said the intention was to at least double, and possibly triple, the team during that year. That was an ambition announced at a particular moment, with the larger organisation still to be built. It gives the financing a human scale: more people working together, more responsibilities to distribute and a shared leadership structure with a growing company beneath it. The next stage meant colleagues as well as capital.
Thompson’s own announcement placed the team near the centre of the milestone. He thanked the people who had built Phoenix and welcomed Valspring as a partner for its next chapter. He also singled out Y Combinator’s renewed participation in a business with a Canadian market focus. The message was celebratory, but its cast was broad: colleagues, investors and the people using the service all had places in it.
Equity + venture debt
Lead investorY Combinator
Returning investorCIBC
Venture debt
The next delivery
The carrier story deserves another look after the funding announcement. It describes a company dependent on something outside its own software, and founders willing to change the software when that dependency failed. That is a particular kind of business problem: the page can load perfectly while the customer experience breaks somewhere beyond the screen. A parcel does not care how elegant the checkout was.
Connecting new carriers overnight gave the founders a way to preserve deliveries during the disruption. It also made their technical background relevant well beyond the launch of the original website. Software capability can remain useful when a business has staff, advertising partners and institutional investors. Some problems still arrive in a form that rewards the ability to build a working connection quickly.
There is a modest lesson here about the shape of Thompson’s career. He moved from developing products for other organisations to helping run one whose products and operations are his responsibility. The change increased the range of things that could go wrong. It also left him with a familiar tool for responding. When the route out of the building stopped working, he and Bache helped connect another route.
“This is just the beginning.”Gavin Thompson · March 2025
Still building in Canada
Toronto remains the setting for Thompson’s public working life and Phoenix’s company story. The company’s path runs through Canadian technology experience, an international accelerator, national advertising and a financing round involving both investors and a bank. Those connections give the business several different audiences. Colleagues need a workable organisation; customers need a dependable service; financial partners need a business that can sustain its plans.
That makes the co-CEO title a larger job than the developer title, without making the earlier work irrelevant. Thompson’s engineering experience is part of what he brought to the founding partnership. The delivery episode gives it a specific expression, while the advertising campaign and financing show how far the responsibilities now extend. He has helped build a company that must be understood outside the software industry as well as inside it.
The most revealing image may therefore be a moving parcel. It starts as something a customer expects and ends as something the company must arrange. Between those points lie the decisions that make an online business real: who builds, who communicates, who funds the next stage and who finds another carrier when the usual one stops. Gavin Thompson’s career has brought him into that whole chain. The next package still has to arrive.