The road less traveled might as well be a part of a small business owner’s morning commute. Many of your favorite businesses — the busy coffee shop around the corner, the family-owned laundromat down the street and the independent movie theater you adore — are the direct result of someone deciding to forge their own path and hope for the best.
And, like many other parts of life, they could all benefit from some extra protection against the unknown. Simply Business offers these businesses a wide variety of insurance options so that they can spend their time making sure your pumpkin spice muffins are fresh and keeping the popcorn machine running.
We sat down with a few members of the Simply Business team to talk about how the company lets them forge their own paths — much like the businesses they serve.
FOUNDED: 2005, expanded to the U.S. in 2016
EMPLOYEES: 700+, 110 local
WHAT THEY DO: Simply Business is an online business insurance brokerage that offers coverage to small businesses and entrepreneurs.
WHERE THEY DO IT: Boston
ON THE ROAD AGAIN: Every year, Simply Business takes the entire team on a trip to enjoy a new city and strengthen their relationships. That’s in addition to the 25 vacation days team members already receive.
CHARITABLE SUPPORT: Simply Business team members are all about improving the world around them. To support this, the company gives them each either $500 to donate to the charity of their choice or allows them two full days to volunteer.
LOOKING TO LEADERS: Every business is a direct reflection of its most important asset — its people. We sat down with a handful of leaders at Simply Business to find out how their success leads to company success.
Jackie Dunn, Digital Marketing & PR Manager
Jackie is responsible for all things social media and public relations for Simply Business. Whether it’s creating content strategy, interacting with customers or providing insights, she’s in the driver’s seat.
FOUNDING FASHIONISTA: Jackie first got the idea for 7th & Willow, her personal style blog, while working in PR and marketing in the fashion industry. Now, she’s working on her own terms.
Capturing a company’s identity is a difficult task. How do you channel Simply Business’ culture and values and carry them through to social media content?
It is challenging to capture a company’s identity, especially one in such a complicated space. Our Facebook, Instagram, and YouTube channels are designed to be more customer-facing, while our LinkedIn page (shared with the UK), is more talent and recruiting focused. For our customer-facing channels, we aim to be informative and relatable. Our voice is conversational and casual. We want to be more of a peer or confidant to small business owners and make sure they know we’re here to help them succeed.
You can only get so much perspective on an office’s culture without talking to someone who works there. How would you describe the environment at Simply Business?
I’ll put it this way — we have the option to work from home whenever we want or need to, and I’m here in the office four to five days a week because I enjoy coming to work. I’ve made some great friends, and I’ve also learned a great deal from my colleagues. It’s a super comfortable and inspiring place to work. Every day is different, and there’s a slim chance you won’t hear me laughing on a daily basis.
We want to be more of a peer or confidant to small business owners and make sure they know we’re here to help them succeed.”
With a growing team, having established relationships to lean on is highly valuable. How does Simply Business encourage collaboration and other opportunities for members to foster relationships?
Establishing relationships is extremely important, especially here at SB. In order for the organization to be successful, it is necessary that we work collaboratively. It’s not even an option. First Thursdays were designed to help foster these relationships.
Every month, one team is tasked with planning an activity for the organization. It can be anything from a scavenger hunt to a murder mystery party. It’s an awesome way to get to know people outside of our team, and it gives you a peek inside the personalities of the host team.
Gabe DeMoraes, Customer Solutions Supervisor
Gabe is one of two supervisors who helps run the Customer Solutions Center, where agents are often the first contact with the businesses they’ll go on to help.
HITTING THE ROAD: If it has anything to do with cars, Gabe’s likely done it. As a big car enthusiast, he does everything from attending car shows, going to track days, working on his own car and hitting the road.
You joined Simply Business as one of the company’s first licensed insurance agents. What’s been the difference maker at Simply Business compared to other workplaces?
Right from the beginning when I was contacted about the licensed insurance agent position at Simply Business, a common theme that was present was opportunity, meaning that there was potential for the business to succeed but also an opportunity to grow with the business.
The biggest difference I’ve felt compared to places I used to work is the willingness for people to listen to each other’s ideas and take them into consideration. At SB, I’ve always felt like I had a voice and that is regardless of tenure or the position you hold.
What lessons from your previous career experiences do you carry into your current role?
In my current role, there are probably two really big lessons that I’ve learned from and that help me do my job better every day. The first is to listen to your team members and to value their input. These are the people who are working with our customers every day and they directly represent SB every time they speak to someone, so we have so much to gain by learning from their experiences.
The second lesson learned is to solve problems by looking at them from different angles. I think this is especially important in a business like ours where we are trying to scale quickly and reach the goals we’ve set for ourselves.
I’ve always felt like I had a voice and that is regardless of tenure or the position you hold.”
You’ve been a part of the Simply Business team for a year. What was your first impression of the company?
When I first started at SB, my first impression was that I felt extremely lucky to have the opportunity to work here. I felt extremely welcomed by my new co-workers in a way I had never experienced before. I know a lot of companies will say things along the lines of “we’re like a family,” but at SB we truly live that.
A year later, that hasn’t changed in the slightest. I still feel like I’m a part of a big family and it’s important for me to keep that theme consistent with my team members.
Sam Pepe, Senior Insights Analyst
If data were the oil that made Simply Business run smoothly, Sam would be a mechanic. As a senior insights analyst, she constantly keeps her finger on the pulse to see what improvements can be made to the CSC’s operations.
FOR A GOOD PAWS: Sam has been volunteering at local animal shelters for a few years now, but recently adopted a little Yorkie of her very own named Charlie. You might even catch them going for walks and chasing squirrels if you’re lucky!
How would you say data plays a role in Simply Business’ overall success?
Data is the DNA of Simply Business, and is found in every decision we make! During such a pivotal moment as a business, data acts as our North Star to indicate if we’ve got the right strategy or if we need to go back to the drawing board.
We always make these decisions with the customer in mind, so our ultimate goal is to provide the best possible experience for the customer. It’s an amazing opportunity as an analyst, as you feel as though you’re creating tremendous value for both your product teams and customers.
I think that if you work hard and earn the trust of your stakeholders at SB, you will be rewarded.”
How do you feel like you’re able to contribute to other parts of the business as someone in data?
Cross-collaboration is essential at SB! We are structured within product teams, so it is essential that each team communicates effectively to avoid becoming siloed. One way the data team helped with this is making a dashboard with snapshots of data from each product team. This not only allows individual product teams to see how they’re progressing but also gives them a peak into what other teams are working on.
You quickly rose up the ranks at Simply Business and have been given more responsibility. How important is it to you to be part of a company that offers a variety of opportunities and upward mobility?
As a young woman in a male-dominated profession, I’m incredibly grateful to work at a company that embraces upward mobility as well as diversity. I think that if you work hard and earn the trust of your stakeholders at SB, you will be rewarded. When thinking about my future at any company, one thing that’s essential is that I know there’s room for me to grow in my role and responsibilities. SB provides me that both in upward mobility and the complex challenges I have the opportunity to tackle.
