My Career Journey: A Resume Told Through Stories
When I was just ten years old, I found myself stepping into the world of work with the Ontario Teen Program (OTP). I walked door-to-door, selling chocolates, tea, peanut brittle, and various other items. I earned a dollar for each sale—a small amount, but at the time, it felt like a lot and it added up. This early venture into sales wasn’t just about the money; it was about the experience and the opportunity that would later shape my career. The OTP even took us on a trip to Disney World in Florida, where our boss kept track of our earnings to cover the cost of the trip. I was the last to sign up, but the first to pay it all off. They called me “Baby Face Ricky” because I was young and good at selling—traits that would serve me well throughout my career.
After my time with OTP, I moved on to Easttown Pizza, which had been voted the World’s Best Pizza in Vegas. I started as a dishwasher, but my drive and eagerness helped me quickly climb the ranks to pizza maker. From there, I transitioned to Outback Steakhouse as the “Blooming Onion Guy.” Yes, that was my official title! I spent my days creating those delicious, crispy onions, and went home smelling great after every shift. Over time, I worked my way up through the kitchen to assistant kitchen manager.
But I wasn’t done exploring my career options just yet. I wanted something different, something outside of the kitchen. So, I took a leap and landed a job at the London Hospital’s vivarium, where I worked with animals for medical testing. It was an unusual job, but it taught me the importance of responsibility, as I kept track of births, deaths, and took care of feeding and watering the animals, especially over weekends.
After some time, I felt the urge to return to the call center world. I got a job at Stream International, providing tech support for HP products. It was a solid job that paid well, so I stuck with it for a while. I then moved to Alliance iCommunications, where I sold TV and internet services for Bell Canada to small and medium-sized businesses through cold calling.
Eventually, I found myself returning to Outback Steakhouse once again, but this time on the front of house as a server. This became one of my all-time favorite jobs. I enjoyed the fast-paced, customer-facing environment, and it was a welcome change from the call center grind. However, I soon found myself bouncing back into the call center world at the Bradford Exchange, where I cold-called customers about collectible items, including baby dolls. I also worked at TD’s call center, activating Visa cards and trying to sell balance protection insurance. However, that job didn’t last long either—it just wasn’t the right fit for me.
The turning point came when I joined Bell Canada’s call center, where I worked selling phone and internet services to incoming customers. I spent a short amount of time there, but eventually, I got bored and made a major decision: I was going to move out west with a few friends. That decision led me to EDS, a company providing tech support for Bank of America employees. It was a different role, offering a change of scenery and a chance to expand my skill set.
My time at EDS and Bell Canada, with all the back-and-forth from Ontario to Alberta, helped me realize that I was ready for something more stable. I settled in Alberta and took a position with Long View Systems (LVS), a tech company, as a Logistics Coordinator—a fancy name for shipper/receiver. While the title wasn’t glamorous, it got my foot in the door, and over the next 12 years, I worked my way up, eventually leading the Cisco team. The company fostered growth, and I found myself constantly learning new things, developing both professionally and personally.
After leaving LVS, I took on a role at Softchoice as a Cisco Enterprise Agreement (EA) Sales Specialist. This job felt like the perfect fit. I loved the work, the company, and most importantly, the people. I thrived in the collaborative environment and the challenges it presented. Then, one day, a recruiter from another company reached out about an opportunity. After some initial conversations and interviews, I found myself embarking on another new chapter, this time leading the Cisco Enterprise Agreement Customer Success Manager team. I am still there to this day and it has been an amazing experience.
From walking door-to-door in the cold winters of Ontario to leading a remote team today, my journey has been nothing short of transformative. I look back with gratitude at each job, no matter how big or small, that helped me learn valuable skills, develop resilience, and understand the importance of persistence. I am where I am today because of the experiences, the people, and the lessons learned along the way.
Each role I’ve had has shaped me, and though my path has been far from linear, I wouldn’t change a thing. Every step, every challenge, and every leap of faith has led me to this point—and for that, I am thankful every single day.
Rick Madsen 