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Our Team

Jonathan GillinghamCEO

Jonathan founded Boss Promotions in 1991 while in university. After establishing a well-respected name for his company, he moved his business out of his mother’s basement and moved into his first office space in 1992 – and the rest, as they say, is history!

Now the proud owner of a 20,000 sq ft office and warehouse in Toronto’s east end, along with the acquisition of two other companies in 2012 and 2015, his entrepreneurial spirit has helped grow Boss Promotions into a $10-million company. Jonathan’s philosophy on the promotional industry has always been simple: Find the right product, at the right price, with the right delivery for your client and you can’t go wrong. His energy and entrepreneurial spirit is infectious and has enabled him to build an incredible team.

Jonathan is the quintessential family man – his weekends are busy cheering on his two athletic children or relaxing up north at his family cottage with his wife. Always on the go, Jonathan spends some of his spare time organizing an annual golf tournament for his buddies that has them playing some of the finest courses in North America. He also hosts a neighborhood rib fest and supports many local charities.

Luckily for us, it’s not hard to convince him to have summer hours, Friday afternoon ice cream for the team, spontaneous lunches for his sales staff, or an office outing to the ballpark. Because Jonathan knows you have to work – and play – hard to win.


Rino FerraraGeneral Manager

Rino joined Boss Promotions in 2008 after many years of managerial experience in the automotive industry. He quickly became an essential member of the team, evidenced by our popular phrase “What does Rino think?”. Along with his General Manager responsibilities, he has been tasked with supervising our office overseas, which requires frequent, long trips to manage quality control, inspect factories and attend industry trade shows. As taxing as this sounds – he really enjoys it!

A steady stream of Italian can often be heard from Rino’s office, which means he’s talking to one of his family members from his home country. Rino is truly a man of the world, evidenced by his adventurous vacations with his lovely wife. Father and grandfather, he can fit anything and anyone into his schedule, including the occasional game of squash.


Winston RichardsonDirector of Sales


After joining Boss Promotions in 2007 and securing several large accounts, Winston soon after founded the Agency Division with the creation of a new team and business development strategy.
Winston’s unparalleled commitment to his clients has been instrumental in the growth of multiple accounts, as well as the development and success of Boss Promotions over a near decade. Working with top brands and marketing agencies across the country, Winston and his team have planned and executed a diverse and impressive lineup of unique promotional products and event activations. Winston works tirelessly to meet the needs of client and brand expectations, while pushing the envelope to create a memorable experience and to secure national brand awareness.
During his not-so-free time, Winston can be found networking on the golf course while occasionally winning a few tournaments, celebrating with his Beaches men’s league slo-pitch team after a third championship win in a row, and of course supporting his beloved Toronto teams.


Jennifer CarmichaelSenior Account Manager – Corporate


Born and raised in Halifax, Jennifer is no small town girl! She came to Toronto after living abroad for a few years in Scotland and Japan. Starting with Boss Promotions in 2005 as an assistant on the Molson account, Jen quickly moved up the ladder and took the lead on other large accounts while learning graphic design in her spare time.
Now, as the Senior Account Manager for Molson Coors, Jen can be seen doing a happy dance every time her custom product designs are brought to life. Understanding the different target audiences for each beer brand has helped her build an amazing library of promotional items. Yearly business trips to China for trade shows and meetings with our office overseas helps keep Boss Promotions on the cutting-edge of designing and manufacturing custom products.
Her vacation time is split between officiating at tennis events (line umpiring for Roger Federer at the US Open was a particular highlight) and chasing around her nephews. Sometimes she actually needs a vacation from her vacations! As our resident baker, Jen happily collects brown bananas to transform into killer banana bread that she shares with the office.


Lisa DoorenspleetSenior Account Manager – FCA

After having a career in film and event planning, it was no surprise that the Boss social event calendar spiked when Lisa joined in 2012. She is the lead on the Fiat Chrysler Automotive (FCA) Account as well as the Chrysler Gear Branded Merchandise e-store, and built a business case to revamp the product offering while improving the customer service experience.

Lisa has a keen and creative eye for trends that resonate with drivers to build brand loyalty. With over 1,000 products her line up, she helps bring the FCA Brands (Fiat, Chrysler, Jeep, Ram, Dodge, Mopar) to life. She can be found traveling across the country to drive sales and strengthen relationships with dealerships and assembly plants, and works closely with the FCA corporate office to create national promotional campaigns used in dealerships and auto shows.
Don’t feel obliged to respond to her emails at 4:30 in the morning – Lisa is the uber carpooler of two athletic girls and is often responding to emails from pools, and rinks before the rest of us even start our day. When she has time for herself she practices yoga, and plays golf.


Alexander PoonAccount Manager – Agency


Arriving in 2011 as a summer student, Alex’s first day on the job was legendary – showed up dressed to kill in suit and tie, only to be put to work in our warehouse doing inventory of T-shirts. After graduating university, Alex joined the team full time and never looked back.
His dedication, impeccable organization skills and his commitment to the job earned Alex the opportunity to manage many of our corporate accounts after a very short time. Now the lead Account Manager for Samsung Canada, he works with Samsung’s head office to develop and maintain an internal ordering web portal for their employees. He also has an important role in our fast-paced agency division – and added a spectacular activation for Skittles to his portfolio.
In and out of the office, Alex’s extracurricular activities mainly involve all kinds of food. You’ll always find someone asking Alex, ‘”what do you want to do for lunch?” in hopes that he’ll suggest a new takeout option for the office since his culinary decisions are always on point. To counterbalance this passion, Alex makes sure that he hits the gym frequently, plays basketball and walks his dog.


Sherrie LuhtalaAccount Manager – Corporate

Sherrie joined us in 2014 with over 20 years of experience in the promotional industry. Having built strong relationships with our corporate clients, such as LG, Tourism Toronto, Sobeys and the Ontario Medical Association, she is a crucial asset to the team. Sherrie always goes above and beyond to get the job done, and can be spotted driving to visit clients in her “orange pumpkin” as she understands the importance of face-to-face relationship building.

Whether it’s stories about her two beautiful children or her two hilarious dogs (or both), Sherrie has a very energetic and unique way of telling a tale that keeps us all entranced. Every Monday, we can expect to see Sherrie sporting a stylish fashion find from her local second hand stores – she has an amazing eye and quite an amount of good luck!


Diana AndreopoulousBilingual Customer Service Representative


Diana is the Customer Service Representative for the Chrysler Gear Branded Merchandise e-store. She brings to the team a strong background in computers, and years of valuable entrepreneurial skills. She has a sharp eye for detail and efficiently manages our stock inventory, billings and invoicing for Fiat Chrysler Automotive (FCA) dealerships across Canada. We always make sure to be on Diana’s good side because she is responsible for the very important role of stocking the vending machine!
As the mother of two growing boys, Diana is constantly stocking up at the grocery store. She can cook up a storm and makes the best Tzatziki this side of the city. After hours you can find her with her feet up, enjoying the sun at the ballpark and cheering on her son at his baseball games.


Helen ElliotSales Assistant – Agency

We were lucky have Helen join Boss Promotions with over 20 years of experience on the supplier side of the promotional industry. She has filled a difficult and demanding role that was greatly needed in our office, and quickly made herself indispensable to our agency division. Her knack for finding some of the most unusual items quickly earned her the nickname “The Sourcer”. And ever since she joined us, she’s been tasked with a very important role – organizing our office lottery pool. We’ll all have Helen to thank when we win it big!

Always the first to offer help, Helen understands the importance of work-life balance and takes time to enjoy the life’s little pleasures, such as spending time with family and her grandchildren, travelling, discovering new restaurants, and cooking up a mean Shepard’s Pie to share with the Boss team.


Louise StrasbourgBilingual Administrative Assistant


Louise is the newest member of our team and brings a strong background in customer service and organizational skills that have significantly increased the efficiency of our sales division. From entering orders, tracking purchase orders, and liaising with suppliers, she is able to keep us all one-step ahead of where we need to be. Known as the strong silent type, humour is not lost on her – crack a joke and Louise will be your best audience.
An early riser, Louise requested to arrive early and start her day well before 9 a.m. This was immediately granted, with the understanding that she is responsible for brewing a fresh pot of coffee for the office each morning!
Outside of the office, Louise has a passion for photography and animals.

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