Accelerating Culture

Advice from a Successful Startup


This past month, Jobber founders Sam Pillar and Forrest Zeisler were recognized for their role in the startup community by the Startup Canada Awards, and received the award for Entrepreneur of the Year for the Prairies.

The Startup Canada Awards, put on by Startup Canada, were first launched in 2014, and will now be entering their fifth year. Given out each year, according to the website, the awards “recognize those driving impact and demonstrating excellence in Canada’s entrepreneurship and innovation community.

Pillar and Zeisler are therefore very honoured to received this award for their company, which has grown tremendously from where it first began.

Jobber, a company directed towards helping small businesses, has impacted nearly 15 million people since inception in 2011. Directed towards helping businesses streamline their productivity and efficiency by cutting out activities that are limiting their growth, Jobber provides a “software that helps home service businesses quote, schedule, invoice, and get paid – faster.

After witnessing the impact that this company has had on business owners across the globe, we wanted to take the time to learn more about the minds behind this operation and what the secrets are to their success.

Sam Pillar, CEO and Co-founder of Jobber was willing to take the time to answer some of our questions:

What first prompted the idea to create Jobber?

“My Co-founder Forrest and I started Jobber after having the opportunity to work with small businesses as freelance software developers. Small businesses and the people who run them are amazing, and we felt like we were able to help them do more, which was exciting to us. We had the good fortune of meeting a really generous and inspiring entrepreneur named Graham who owns a painting company and needed help running it more efficiently. He became our first customer way back in 2011 and is still with us today.”

What does winning this award mean for you and the company?

“Winning the Entrepreneur of the Year Award for the Prairies is above and beyond anything else a testament to the world class team we’ve built here at our headquarters in Edmonton, and more recently in Toronto. We’re servicing customers in over 45 countries who are delivering billions worth of services annually using Jobber. We are a globally competitive SaaS business, doing amazing work with an HQ in a pretty non-traditional place. I think that’s an exciting start and am tremendously encouraged about what’s possible for us here in Canada, and more narrowly, in Alberta.

What would you say was the most important thing your company did that led to your ultimate success?

“I honestly don’t think we realized we were doing this early on, and therefore it’s questionable as to whether we can take any real credit for it, but we were very customer focused from the beginning. We spent a lot of time talking to our customers and potential customers to get in front of them as often as they would allow us. I think this helped us develop a deep respect for the work our customers do, and a genuine empathy for the challenges and struggles that they face in doing what they do. It’s our job to help them with those challenges, so understanding them in the first place is important. This is something we continue to build into our organizational culture to this day, and I believe it’s critical to our long-term success.”

Reflecting back to the beginning, what is one thing you would’ve done differently in developing your company?

“I think we’re in the relatively fortunate position of not having anything obvious to point at as being something we should have done differently in the early days. That’s rare, and I chalk it up entirely to luck. What can’t be chalked up to luck though, is the guidance, advice and contributions that you get from the people who are involved in the business early on, either at the core or the periphery. We were lucky to get great advice early on from informal advisors, the best early investors you could hope for, and an amazing early bench of senior people to help run the company. If I could go back and do it again, I think I would just spend more time earlier on making sure to get as much outside perspective, opinion, guidance and help as possible.”

Where do you see Jobber 5 years from now?

“Five years ago, Jobber had barely started making headway, and today we’re powering billions of dollars’ worth of annual service delivery on behalf of home service businesses all over the world. It’s difficult to predict where we’ll be five years from now, but what I do know is that we are very early on still, and there’s an opportunity for Jobber to help millions of small home service businesses out there. That’s what we want to do, and that’s what we’re going to work towards over the next five years.”

What advice would you give to those who are just starting out in developing their own company, and hope to one day be in your shoes?

“I have two pieces of advice for people just starting out that I feel are battle-tested and realistic. The first is to make sure that you’re doing something you really care about. At Jobber we talk about “giving a shit,” as a core value of our culture, and this principle applies all the way back to the genesis of the company. We really care about the success of small business people, and that’s been true since the company was just two people: myself and my co-founder, Forrest. The company building journey is a grind. It’s hard. Doing it because you really give a shit about the outcome it creates is important to ensuring that you can stay the course.

The other critical element to being able to stay the course brings me to my second piece of advice, which is have a co-founder. Starting and building a company is really hard, and how it’s hard changes over time. I don’t think either Forrest or I could have done this on our own. The fact that we both have it all on the line, and both really care about what we’re doing, means that we can support each other in a way that is truly unique. I highly recommend anyone looking to start a business have a partner in the journey; I’m sure glad I did!”



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