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Living On The Bleeding Edge — Sam Pillar of Jobber

I had the pleasure of interviewing Sam Pillar, CEO of Jobber.


I had the pleasure of interviewing Sam Pillar, CEO of Jobber.

Gene: Thank you so much for taking the time to speak with me. Please give us a brief overview of your background and how you got started in this industry.
Hi Gene, thanks so much for having me. Brief background on me is I spent my early years in Vancouver, Canada, spent a couple years in Toronto, Ontario and Regina, Saskatchewan, and ultimately went to university in Edmonton, Alberta, Canada at the University of Alberta. I’ve been a computer nerd my
whole life, and spent my first few years studying Computer Science, but developed an interest in Intellectual Property law and graduated with a Commerce degree focused in business law. Out of school I pursued a career in management consulting but quickly decided that was not for me, and
while I was contemplating my next career move, I started doing freelance software development for small businesses and NFPs. One of those consulting gigs was for a small home service company here in Edmonton that was looking to improve their organizational efficiency and deliver better service to their clients. I spent a lot of time with the teams there, and saw a lot of inefficient, manual work being done by the crews just to get from one job to another, figure out what they were supposed to be doing on site, and interacting with their clients. This experience gave me the idea to start working on what would ultimately become Jobber. So, I’m working on this new project one day, literally at a Starbucks in Edmonton, when an engineering grad from U of A named Forrest Zeisler introduces himself and asks me what I’m doing… Forrest is a great software developer and also a freelancer at the time, so I show him what I’m working on and we
chat about it for a while. It just so happened that Forrest was friends with someone who works at a painting company that was looking for exactly this kind of software. We started collaborating together on this project alongside that painting company, getting new updates in front of them every couple of
weeks and gathering feedback. Fast-forward a few months, and we co-founded a new software startup called Jobber!

Gene: Can you please tell us more about what your company does? I love learning about cool new tech, so please feel free to geek out with me on this.
We have a software app for small mobile service businesses (think: the people who cut your lawn, or clean your house, or repair the HVAC in a high rise) that allows them to quote, schedule, invoice and get paid. From a tech perspective we have always looked to use the most advanced, but proven tech across our stack. From our mobile apps and APIs to our tools that sync our customer’s data with the rest of the SMB software ecosystem, like Quickbooks and Xero for accounting, for instance.


Gene: Who are your competitors in this space? What makes your company stand out?
Our biggest competitor by a country mile is spreadsheets, carbon copies and other ways to say “pen and paper”. We really focus on standing out by educating small service businesses on the value software can bring to their business. It makes it so much easier for them to manage their teams, manage their clients, and deliver the best possible service to their clientele. In terms of how we stand out the best way to describe that is simply to make the app as robust and capable as possible, while always optimizing for simplicity and ease of use. A lot of our users are workers out in the field, so reducing the amount of cognitive burden they carry to accomplish tasks is a huge
focus and differentiator for us. For office staff and the business owner, we try and always provide the easiest path to accomplish many tasks at once. As an example, we want to ensure that you can invoice every customer that is currently carrying an outstanding balance with a single click at the end of the month, while allowing the consumer to pay our service provider customer with a similar “one-click” solution.

Gene: What sort of traction have you guys gotten so far? Are you a well-known brand? Still in the startup stage? Or somewhere in the middle?
I would suggest we are somewhere on the cusp of having a highly recognizable brand. As I mentioned before — the vast, vast majority of the market is still not turning to software instinctively to help them run a better business, so we still have a lot of work to do there. Our customers are delivering billions of dollars’ worth of services every year with the help of Jobber, so there’s a certain amount of scale there, but we’re just getting started!

Gene: What is the most innovative project that you have ever worked on?
Building a startup! Honestly, while it sounds cliché, the overarching “project” of building this company, from a couple of software developers, to over one hundred smart, dedicated, highly coordinated people who care deeply about the small businesses we serve and the challenges that we solve for them is far
and away the most innovative project I’ve worked on. This is the first company I’ve built (and I use the term “I” very liberally here), and I’m constantly surprised at both the known unknowns, and unknown
unknowns that crop up and need to be solved for. Building an organization and a team that is so supportive, humble, and that really gives a shit means that “I” am not really building this company , “we” are. Simple as it is, I think that’s a pretty innovative and scalable solution to one of the most
important business building challenges.

Gene: Who is your hero (In your business or personal life)? How have they inspired you to become the person you are today.
Definitely my parents, in equal measure. They provided the support, encouragement and structure that made me what I am today, for better or for worse! I want to find ways to put more back into the world than I take from it, and it’s because of the kindness, energy and tenacity I’ve seen them live their lives with.

Gene: If you could jump into a time machine, go back in time, and change one aspect of your past, what would it be, and why?
That’s a tough question — it feels like going back in time to make a change implies regret, and I don’t have any regrets.

Gene: How will the work, your team is doing impact humanity in the future? For example, bringing people closer together, creating more jobs, create killer robots that will destroy all of humanity (joking), etc.
In all honesty, when we look at employment trends in the US, the rise of the gig economy worker and the continuous increase in incentives and programs to encourage entrepreneurship, we get extremely excited about the future and our place in it. We help people build the life and the career they want to
have, and we help them be self-sufficient, and create meaningful relationships with their clients, doing more of the things they love to do. That’s pretty good in my books. Amplify that impact globally and we
are very excited about what the future holds.

Gene: Throughout our careers, we have all run into a few roadblocks. Can you please tell us about a time that you failed? How did you motivate yourself to keep going?
Back in 2014 I hit the road to raise capital for Jobber and failed. I suppose in hindsight it wasn’t a great time to be raising, and the market wasn’t super eager to be investing into a small startup based out of Edmonton, Alberta. I was on the road for the better part of 4 months before pulling the plug and
regrouping. We felt pretty dejected at the time and looking back it was kind of a dark period actually. The most important factor in getting through and staying focused (in that, and many other challenging times) was having an awesome co-founder who is as deep in it as I am. We’ve found that our emotional state tends to oscillate out of phase, which really helps us to keep each other level. It was also incredibly important to have helpful, supportive early stage investors. Supportiveness is a theme that was established early at Jobber, and I believe will continue to be critical in the future.

Gene: What advice would you give to an inexperienced founder of a technology company?
Don’t do it alone; have a co-founder, and focus all of your energy early on building something that you know people actually want. But don’t wait too long to start selling!

Gene: If you could spend one day with any person (alive or not), who would it be any why?
Warren Buffett … why not learn from the master? His consistency over time is beyond impressive, and he seems like a very down-to- earth guy, which fits well with our values.

Originally published at medium.com

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