More than US$100 billion worth of lawn care, plumbing, cleaning, and HVAC work has run through Jobber, software that started with one painting company and a stranger (now the co-founder) asking what Sam was building at an Edmonton Starbucks.
Today, over 100,000 service businesses in 70+ countries use it to quote, schedule, and get paid. On November 2, co-founder and CEO Sam Pillar takes the Together Toronto stage to tell the story behind it.
It started with one painter
In 2010, Sam was a freelance developer watching an Edmonton home service crew lose hours to manual work between jobs. He was building a fix at a Starbucks when another freelancer, Forrest Zeisler, introduced himself and asked what he was working on. Forrest knew Graham Audenart of Painters Enterprise, who needed exactly that tool, and Graham became Jobber's first customer and remains one to this day.
A market everyone else skipped
Field service software existed for utilities and big enterprises, but Sam noticed nothing was built for a 10- to 15-person landscaping or plumbing company. Building for those crews became Jobber’s edge.
Betting on Edmonton
Sam could have moved to a bigger hub, but he chose to stay. “In other major tech hubs, talent is expensive, and retention is really difficult,” he said in 2019, and in Edmonton, no other company like Jobber was competing for that talent.
That choice came with a cost. In 2014, Sam spent the better part of four months pitching investors and returned without a yes, at a time when few were eager to back a small startup from Edmonton. What got him through, he said, was a co-founder who was in as deep as he was.
Nine years later, General Atlantic led Jobber's US$100 million Series D, and total funding now sits at US$183.5 million.
Jobber | 2011 | 2026 |
|---|---|---|
Customers | 1 painting company | 100,000+ businesses |
Team | 2 freelance developers | HQ in Edmonton, plus Toronto, Vancouver, Kitchener-Waterloo and Boston |
Reach | Edmonton | 70+ countries |
Work run through Jobber | One painter's jobs | US$100B+ in services |
This fall, Jobber launched Jobber Teammate, an AI agent that briefs owners each morning and drafts their quotes. It also became the first Edmonton-founded company in Endeavor Canada's network.
Key takeaways
Sam kept putting Jobber where it could be the only serious option, the first software built for a 10-person crew and one of the few SaaS employers in its city. That room let him grow, which is how a company that couldn't land a round in 2014 became what Endeavor calls one of Canada's most successful software companies.
Whether you're looking for the right co-founder, coming off a raise that didn't close, or building for customers nobody else is chasing, Sam has been there. Come hear what kept him going at the Together Toronto stage on November 2.
📣 Put Your Startup in Front of 400+ People
We’re showcasing 35+ startups at U of T Schwartz Reisman Innovation Campus before Together Toronto’s speakers (Sam Pillar, Andrew Lockhead, Noah Buchman, and Vanessa Galarneau) take the stage.
Meet investors, get in front of customers, and connect with founder accelerator programs across U of T and the Vector Institute, from UTEST to the Black Founders Network.
🚀 Montréal Rocketships Are Here
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The Night Before: The Growth Table
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