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Sam Pillar: “To create a fantastic work culture, there needs to be clear lines of communication within organizations”

As a part of my series about how leaders can create a “fantastic work culture,” I had the pleasure of interviewing Sam Pillar. Sam is the CEO and co-founder of Jobber. Throughout his 15-year career as a software developer, management consultant, and founder, he has embodied the entrepreneurial spirit. While working alongside companies to understand […]

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As a part of my series about how leaders can create a “fantastic work culture,” I had the pleasure of interviewing Sam Pillar. Sam is the CEO and co-founder of Jobber. Throughout his 15-year career as a software developer, management consultant, and founder, he has embodied the entrepreneurial spirit. While working alongside companies to understand their problems and build software solutions to help them move faster, he recognized an opportunity to improve the inefficient, manual work being done by these small businesses, many of which operated within the home service industry. This led him to found Jobber, an award-winning SaaS platform that helps small home services businesses organize their entire operations, from scheduling jobs and managing their crews, to invoicing customers and collecting payments. Since launching in 2011, businesses using Jobber have serviced over 10 million people in more than 43 countries, delivering over $6 billion annually, and growing, in services to their customers. Sam holds a bachelor’s in business law from the University of Alberta.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

Iwas always interested in the inner-workings of everything around me. As a kid, I liked to break apart my parent’s electronics like VCRs and radios to see the mechanics behind them, then put them back together. The fascination in creating something led me to coding and my career as a software developer. For years, I was a freelancer and had the opportunity to work with small businesses. That’s where I witnessed the challenges that these organizations were having just operating their businesses. The technology solutions available to them at the time were archaic, if non-existent. It felt like there was a ton of opportunity for me to help these organizations, especially in the home services market.

I worked out of coffee shops a lot, and that’s where I met another local developer, Forrest Zeisler. Forrest and I got to talking one day and I told him about the idea I was working on, which would eventually become Jobber. It just so happened that Forrest had a friend who owned a painting company, Graham Audenart of Painters Enterprise, who was looking for a software solution to help organize his business. Forrest was interested in partnering with me immediately and Graham became our first customer. And the rest is history. Graham is a Jobber customer to this day!

Since Graham, Jobber has helped thousands of small business owners achieve success, whether that means growing their companies, spending more time with their families, or engaging constructively in their communities. We are really proud that the work we do here at Jobber ends up having such an impact on real people and communities.

Can you share the most interesting story that happened to you since you began leading your company?

In the nine years since we started the company, I’ve been amazed by the response and enthusiasm for Jobber. It’s difficult to pick a singular story or incident as there are so many, but the moments that stick out are when friends, family members, and employees share how they have come across Jobber “out in the wild.” It’s not uncommon for team members to come up to me throughout the workday and share how their cleaner, plumber of even lawn care company uses Jobber. I’ve even had family members reach out to me sharing how they’ve received invoices delivered through Jobber. Jobber exists to help small businesses succeed and to make our customers’ lives easier, so for me, this feedback reinforces our mission. It’s proof that these organizations are using the Jobber platform and are successful in their fields, which is ultimately what we set out to achieve. Jobber is servicing the ‘little guys’ to help them succeed and we’re happy our employees are so excited about having that kind of impact.

Are you working on any exciting projects now? How do you think that will help people?

We’re always looking to enhance our platform with new features that our customers tell us they want and need. Just recently, we announced several new features that will help our customers boost their sales and marketing efforts. Jobber users can now leverage online booking capabilities, automated customer quote follow-ups, and integrations with marketing automation platform, Mailchimp, and online task automation tool, Zapier.

Ok, lets jump to the main part of our interview. According to this study cited in Forbes, more than half of the US workforce is unhappy. Why do you think that number is so high?

I think happiness is a big, complicated issue, and far be it for me to presume that I have any business making claims about it. As an employer, you have to recognize that people spend most of their life at work, so naturally they crave meaning behind what they do. It’s the sense of contribution and meaning that impacts happiness.

At Jobber, we try to create an environment where people get a strong sense of contributing to the bigger picture. We exist to make small businesses more successful and that is what drives each employee. We place a lot of attention toward making sure the people in our company know why we’re doing what we’re doing, so that each person feels the impact that we have in helping small businesses grow. This is one of the reasons why we developed an internal concept called Voice of Customer. We share customer feedback through our Customer Success Team and spread it across the organization in real-time through a Slack channel. Whether the feedback is a problem that a user is having, or a success, we share it. It’s like a firehouse of information that gives everyone a window into the life of a small business that is unfiltered and raw. Voice of Customer has become an important measuring stick of our success at Jobber and has also been a great platform for us to showcase how the whole of our efforts is so much greater than the sum of its parts.

Based on your experience or research, how do you think an unhappy workforce will impact a) company productivity b) company profitability c) and employee health and wellbeing?

A common problem is that some companies are willing to trade employee happiness for short-term productivity and profitability, which is extremely short sighted. The cost to fill a vacancy in, say, sales, is about 2.5x the salary of a salesperson. It’s expensive to rehire. Therefore, it’s advantageous for a company to keep their employees happy and engaged.

Companies really need to consider employee happiness to achieve organizational success. When an employee is unhappy, he or she is more likely to produce bad work. Even worse, that unhappy employee has the potential to negatively impact the company’s culture, which is unequivocally bad for business. An unhappy workforce negatively impacts the productivity, profitability and health and wellbeing of employees. Unhappiness festers within an organization, which is why at Jobber, we do everything we can to create an environment where people care about our mission. Even more, we want our employees to know that we’ve invested in them just as much as they’ve invested in us.

Can you share 5 things that managers and executives should be doing to improve their company work culture? Can you give a personal story or example for each?

  • Walk the walk and talk the talk

When you’re in a leadership role, it becomes a lot harder to “walk the walk” and “talk the talk.” Leaders need to lead by example and show they care for the success of their employees as well as their customers. They need to behave at a standard they would want everyone else to be held accountable to. As a company, you need to provide a level of consistent, high-quality service to customers, while also ensuring that you are meeting the needs of employees internally. I’ve worried about sounding like a broken record when repeating our company’s mission and values, but I have realized that repetition is crucial to ensuring everyone is on the same page and there’s no miscommunication among the team.

  • Embrace constructive feedback

It’s important that constructive feedback is a regular habit so people understand how they can continually improve. One-on-one’s are a crucial part of creating an environment where trust can be developed, and feedback can be provided openly. This should happen every week or every other week, at minimum, and importantly, feedback should be provided in both directions.

  • Don’t just share the limelight, try to give it away as much as possible

Leaders are often credited for the successes of their team. In those cases, it’s important to celebrate with the wider team and shine a light on the people who contributed to the win and deserve the recognition. A true leader understands the value and importance of taking a back seat when credit for accomplishments is being given.

  • Check in on employees

As a company scales, it’s imperative to go hard and fast to continue growing. However, during this drive for success, it’s easy for employees to get lost in the shuffle. Remember that people are complex. It’s important to check on the overall mental wellbeing of the individuals you work with to ensure they are in the right mindset to be productive at work.

  • Never stop learning

Just because you are a manager, doesn’t mean you are done learning. High-performing managers are always looking for ways to improve their skill sets and expand their knowledge. This can come in the form of formal classes or leadership books or even just by keeping an open mind and truly listening to the people you work with. Afterall, a manager is only as successful as the team he/she leads.

It’s very nice to suggest ideas, but it seems like we have to “change the culture regarding work culture”. What can we do as a society to make a broader change in the workforce’s work culture?

Some organizations believe that a strong workplace culture is all about the perks — a well-stocked kitchen, tons of vacation days, and schedule flexibility. These are nice ways to show employee appreciation, and certainly these are things offered at Jobber. However, I think what’s more important to people is a sense of progress and development, such as having some transparency into their career path and growth. We need to ensure that there are clear lines of communication within organizations, so that employees understand how they’re contributing to the overall company mission, and how they can grow as individuals while supporting the common goals of the business.

How would you describe your leadership or management style? Can you give us a few examples?

You’d have to ask the people I work with to get a true answer. I’d like to think my leadership style is complementary. I’m lucky to surround myself with a team that complements my skills and abilities very well: they help amplify my strengths and compensate for my weaknesses. At Jobber, I am not one person leading the organization — it’s a team effort and I rely on the expertise of my team.

It’s also important to me to try and get to know our people. After a new employee has been with Jobber for six to eight weeks, I have a one-on-one discussion with them about their experience so far. I ask for their feedback about their experience, what we are doing well, and what we can improve upon. I want people to know that I’m open to feedback and criticism and want to hear about how they think we can build a better company.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I am very grateful to Jobber’s first customer, Graham Audenart, owner of Painters Enterprise. When my co-founder and I were first developing the idea of Jobber, he was right there with us. He was incredibly generous, patient and understanding, and honestly, one of our biggest inspirations. Graham was willing to give ‘time’ to us, which is one of your most valuable resources as a small business owner.

Graham’s generosity and patience are definitely pillars of a leader and entrepreneur that I still embrace today. It’s been amazing to see how he has been able to significantly streamline operations and grow his business using our platform. Since we first met, he’s expanded his own team and service offerings. Graham is a real celebrity inside the company; everyone knows who he is and to this day, he’s still very giving with his time, visiting us frequently, sitting on customer panels, and joining us at industry events.

How have you used your success to bring goodness to the world?

We established Jobber Cares four years ago. An internal program with its own operating budget, Jobber Cares supports employees in giving back to their surrounding neighborhoods in Toronto and Edmonton, where our offices are located. Each year we conduct an annual survey of our people and create an open channel of communication so employees can tell us what kinds of community outreach efforts are important to them. Some past activities have included volunteering at shelters and food banks and helping to build homes through Habitat for Humanity. Jobber Cares creates a culture of inclusiveness and collaboration. Our goal with the program is to create a sense of personal accomplishment for employees.

In January 2018, Jobber also launched JUMP, a company-sponsored initiative to help post-secondary students make the leap from post-secondary education to careers. JUMP plans and executes five to six events a year — such as panels and workshops — and it’s fully run by Jobber employees who volunteer their time and skills to teach others. JUMP provides a great opportunity for development in teaching, leadership, and public speaking. And most importantly, it allows us to execute our company values: “Be Humble” about our experience, “Be Supportive” of others’ career journeys, and “Give A Shit” about the community that supported us.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life? “

One of my favorite quotes is from Bill Campbell, “Your title makes you a manager. Your people make you a leader.” Being a manager is more than just overseeing a team — it’s also being invested in their success. A leader is one who inspires their team to put their best work forward, and one who does so with honesty and integrity. Leaders are strong communicators and know the power of delegation and team empowerment.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I think by co-founding Jobber, I have already inspired a movement. Our employees care deeply about the work we do and see how it benefits small businesses across the globe. I’m proud of the culture we’ve created at Jobber and how we will continue to reinvent our culture as we grow and scale in the future. What inspires me is not only the commitment of our employees, but the impact of our customers too who are our cheerleaders. They are constantly suggesting new solutions to us and our engineers are always hard at work making it happen. It’s truly amazing to be leading this organization and I can’t wait to see what lies ahead.

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