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Jobber co-founders Sam Pillar, left, and Forrest Zeisler, right, provide software to help small, often home-based businesses with invoices, bookings, payments and the other administrative tasks.

Jobber/Handout

Sam Pillar and Forrest Zeisler met a decade ago in an Edmonton coffee shop they used as ad-hoc offices while working as freelance software developers.

They started chatting and eventually Mr. Pillar shared an idea he had to build software for home services businesses such as painters, window washers, residential cleaners, and landscapers. 

Mr. Zeisler was in.

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The pair worked for months on the software to help these small, often home-based businesses with invoices, bookings, payments and the other administrative tasks many entrepreneurs were still doing by hand in notebooks or on Post-it notes.

“We felt we were really onto something,” Mr. Pillar says. 

And they were. The pair formed Octopusapp Inc. in October 2010 and launched Jobber, the name they operate under, in 2011. Today, the Edmonton-based field service software company has 220 employees and 90,000 users in 47 countries.

Writing the software wasn’t a problem for the pair of developers. Building a business, though, was a greater challenge.

“We were able to just put our heads down and write software. I think a lot of people forming companies face the challenge of not having that skill set but we didn’t have that,” says Mr. Pillar, Jobber’s co-founder and chief executive officer. “But it meant that we actually spent the first couple of years building the product, and iterating, and not necessarily getting to building the business.”

The technical expertise that made it so easy for the pair to develop the platform posed a challenge to scaling the operation. Given their backgrounds in software development, they were initially reluctant to outsource their technical needs.

“We built our own custom admin CRM (customer relationship management) system and quickly realized that, as a software company, you can’t be building your own software internally,” Mr. Pillar says. “You’ve got to build your product that you’re good at and let other people build the products they’re good at and you should just buy those products.”

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From the early days of cold-calling businesses out of a phone book, Jobber now has a customer support team of more than 30 people. 

After the failed CRM experiment, the company tried several off-the-shelf platforms and now uses a custom mix of Zendesk and Intercom messenger software.

“What we have today has come through a lot of trial and error, not just which tools but how to use the tools,” says Mr. Zeisler, Jobber’s co-founder and chief technology officer. “We had to find the right blend and then figure out how to connect them so we could get the best of both worlds.”

They went through the same process to find the right phone technology.

“You can’t be afraid to keep experimenting until you find the right recipe for your unique business,” he says.

Mr. Pillar and Mr. Zeisler went so far as to press the pause button on hiring a few years into the company’s journey until they had the right tools in place.

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“We went forward and resumed when we knew we could handle it,” Mr. Zeisler says.

Their aim has been to build every system on a foundation that will be able to continue to scale and grow, he says. And at the centre of that is customer service for a very wide range of customers.

“We’ve got younger people right out of school deciding to start their very first business, who grew up on technology and have very high expectations and are extremely capable, who will decide if there’s something that isn’t quite suiting their needs they’ll go and write code against our API [application programming interface] to build their own internal tools to extend our product,” Mr. Zeisler says. 

“And then we have businesses that have been operating the same way for 30 or 40 years, out of a filing cabinet, that decided it’s time to make the leap but are still a little scared. This is where it’s not just one tool but a lot of tools across a lot of teams and making sure everything’s connected.”

By integrating outside tools like Zendesk and Intercom into their own system, Jobber has created a centralized data warehouse. From here, they flow the information to both internal dashboards for their own performance management, and to customers for theirs.

In 2012, the company raised its first round of seed capital from Vancouver-based Version One Ventures and Berlin-based Point-Nine Capital, but they got much more than money. The investors on their board became mentors, guiding them in the business of building a business.

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Boris Wertz, the founder and general partner of Version One Ventures, was one of those early investors.

Ten years ago, it was very difficult for small- and mid-sized companies to leverage technology, he says.

“Any software tool that brings the same technical opportunities to small- and mid-sized companies that big companies have is exciting for us,” Mr. Wertz says.

“It’s pretty magical what you can do today as a small business and that certainly levels the playing field for small companies.”

He credits Mr. Zeisler and Mr. Pillar for building a strong foundation for the company. They understand their customers and have built a great product for them.

“My single most important advice to any entrepreneur, especially at the early stages, is get the product right and make your customers happy,” Mr. Wertz says.

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Jobber now gains more customers in a month than the company had in the first four years of business, and it is still in the relatively early days of development.

Platform users do $6-billion worth of business each year, Mr. Pillar says. 

“That’s $6-billion worth of lawns mowed and sinks fixed and roofs repaired and apartments cleaned,” he says. “And there are millions and millions of these small businesses in North America alone, so it’s still early days for us.”

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