Two strangers kept ending up at the same coffee shop tables in Edmonton.
Sam Pillar and Forrest Zeisler were both freelance programmers, each working on a personal project, each hunched over a laptop in the cafes that gave them cheap caffeine and a place to sit. They noticed each other because they kept noticing each other. Eventually they talked.
So the two freelancers built it, listening closely to what the painters said they needed.
Neither was building a company that day. They were building a living. Zeisler happened to know someone at a local painting business that wanted software to keep track of clients, quotes and invoices. The painters did not need an app that would change the world. They needed their paperwork to stop eating their evenings. Pillar later recalled being excited simply to be solving a real problem for a real business.
So the two freelancers built it, listening closely to what the painters said they needed. Then they did the obvious thing: they asked who else had the same headache. Plumbers, landscapers, cleaners and electricians turned out to have exactly the same one.
The ambition at the start was almost comically small. As it has been described, the target was US$10,000 a month, enough to cover costs and pay the two of them a modest salary. That is the part the later headlines leave out. Jobber did not begin as a plan to build Edmonton's biggest technology company. It began as a plan not to need a boss.
What nobody quite expected was how patient it would be. Jobber took its first real institutional money in 2015, an US$8m Series A led by OMERS Ventures. A quiet inside round followed in late 2018, which Pillar counts as the Series B. Even then the company had raised only about US$16m in total. In January 2021 Summit Partners led a US$60m round. By then more than 100,000 service professionals in 47 countries were using the product, and recurring revenue had grown 90% in a single year.
The price of building in Edmonton shows up in small ways. When the company wanted to hire people it called software engineers, it ended up in a legal dispute with Alberta's engineering regulator over what that phrase legally means. The pandemic brought a short hiring freeze, then more hiring.
In February 2023 General Atlantic led a US$100m Series D, the largest venture round in the city's history. Pillar said Jobber had not needed to raise, and described the terms as founder-friendly. His guide, he said, was Warren Buffett's advice to be greedy when others are fearful, and Jobber had spent the boom watching rather than splurging.
The pattern is easy to miss. Pillar and Zeisler never needed to guess at a market. They had one customer with one paper problem, and they built until it went away. Everything after that was repetition, done more carefully than their competitors thought necessary.