Interview with Jonathan Scott – Charleswood Roofing

Company: Charleswood Roofing     |     Website


So, today’s interview is with a very physical hardworking entrepreneur, Jonathan Scott. He is a long-time business owner who has a team dedicated to replacing shingles, soffits and eavestroughs here in Winnipeg, Manitoba. Jonathan and his crew offer extensive and professional services including exterior makeovers.

Interested in this service and curious to find out more?

Now let’s hear what Jonathan had to say …


How did you continue to ignite that fire within you?
The fire continues to be ignited with each roofing project and exterior renovation which gives us the peace of mind and satisfaction that we are continuing to make Winnipeg great, one roof at a time.

Did you start with a business plan? If so, tell me a bit about your vision and mission.
It wasn’t a formal business plan. We kind of decided we were going to just go with the flow and start off small. Then we quickly realized we needed to offer a complete service. People didn’t just need roofing improvements. A lot of what we found out early on in roofing work was going to be tied to other exterior and insulation improvements. As far as the business model goes, we usually slow down in the winter. Then we do a debrief of how we can be better and where we need to improve.

What are some of the biggest challenges you feel your company is faced with?
We are seasonal and the roofing work we do is weather dependent so that’s always a huge challenge because historically we are very busy in the spring, summer and fall so we only have a short period of time to get to all our customers. Also, working on different types of house, existing homes and new construction, we are always running into new challenges so it’s kind of an ongoing challenge right there.

Walk me through a typical workday – from when you eat breakfast in the morning to what you think about on your commute home THEN tell me about what you think about when you’re not in “the office”?
My day starts as soon as I get into my truck. It’s my mobile office. LOL! I usually start getting to my messages and mapping out my day. Once I get to my office, I check my emails an see where my crews are going to be dispatched for the day then decide if I need to be at the office or on the road. Most of my days are spent on the road visiting various addresses, doing estimates and project planning. Sometimes it takes me until the end of the day or I will end up back at the office offloading paperwork, following up with customers and planning for the next day.

What were some of the biggest challenges you’ve had to overcome to get to where you are today?
Keeping up with the demand which translates to a level of quality customer service. I have needed to hire and train as the business grows. Another challenge that’s interesting is the industry is pretty cut throat, price point is an obstacle and that comes up often. Competing with other companies in the same industry I have learned that promotion is key and to present what sets us aside but at the end of the day our market is very much about price point, so it’s always been a challenge to be constantly doing new quotes, so my crew isn’t’ just sitting around doing nothing.

Can you tell me about your ideal target market?
What you really want is a client who wants to open up to listening about their particular project. A lot of times people just want to know the price right off the hop and keep the blinders on when it comes to feedback or suggestions that we may have discovered to improve their roof or their exterior. So, the ideal client would be someone who is willing to listen, let us explain and let us help them compare some of the quotes they received for said project. We always try to direct our customers to our showroom so that they can see that we are very serious about what we do. Awe just love it when a customer is willing to come down to our showroom and just take in the whole experience. We want our customers to be as serious about planning their project as we are!

Looking forward into the next few years, what projects or goals are you most excited about?
Growing the business to be the biggest residential roofing and exterior contractor in Winnipeg and it’s surrounding areas. I want Charleswood Roofing to have a reputation for great customer service. I also want us to continue to grow with some of our bigger customers so that property managers and developers see that it’s one of our goals in the near future. I will also be expanding and renovating our office and our showroom which will better serve our customers and our staff.

If an entrepreneur asked for your advice and you only had a few minutes to give them your best tip, what would it be?
Write down all of your goals and your dreams. Follow up on them and never rule anything our. Don’t think an idea will never happen again. If you have a goal to do something or build a certain business or even develop something don’t get discouraged. Also, don’t let other people discourage you by their comments. Always pursue and know that anything is possible.

Pick one thing in your life you may go back and do differently. What would it be and why?
I don’t really think of it as regrets, so I guess I don’t have any. But with that being said, I would have liked to have become a summer counselor at Camp Cedar Wood when I was a young adult. I didn’t pursue it even though I was really interested. If I could go back, that would be the one and only thing I would do differently.

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Crystal Kordalchuk

Crystal is an artist, a writer, an organizer, a dreamer, a doer, and down-right proud of it NERD!.

Struck with a love for #AllThings creative at a very young age, Crystal dreamed of a life fueled by her passion for creating and bringing the stories and images in her mind into reality.

As she worked toward her dreams, she earned a diploma as a Computer Applications Specialist then another in Graphic Design and from there began to develop her extensive background in multimedia and the arts. She began her worked in the magazine industry as a layout designer and had a succession of design jobs thereafter. It was her role as a graphic/web designer that gave her the first real glimpse of her future. Soon she began a side job as a freelance designer while keeping one foot in the corporate world. A spark was lit! She turned her freelance gig into a full-time business combining design work with her other passion: creating organization from virtual chaos.

Crystal is one of the most organized individuals on the planet. She is by all means a Zen master of her crafts. She excels at helping others become “untangled” and provides her clients with tools to run their businesses smoothly while she takes care of the details behind the scenes. Thus Virtually Untangled was born. A successful business where her work as a top notch creative in graphic and web — with a twist of virtual assistant — married into one amazing place where clients can come with their virtual messes and become magically untangled. Crystal can always make sense of even the most unorganized chaos and offers a virtual detox of order and peace, so her clients can get busy doing the work that they love the most.

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