Travelweek: You’ve had an amazing travel industry career, and you’ve worn so many hats – including travel agent! Can you walk us through your 30+ year career? 

Jackson: “I feel incredibly fortunate to have had such a long career in the travel industry – even though I did dabble in other things at the same time, like owning a franchise of dollar stores and working as a volunteer facilitator for a consulting firm.

“I started right out front as a receptionist for a small travel agency in North York. I was doing this as I finished Seneca College for Travel and Tourism. After I graduated, the owners moved me to a ticketing agent; back then, I believe I hand-wrote all the tickets. Used OAGs, and validated the tickets with actual airline plates on a small machine similar to a credit card validator. I can still remember the availability code for ReserVec  … DAV0700Y12SEPYYZYUL1. Ask me codes for anything since, and no way could I remember.

“Needing to make more than $9,000/year and working part-time at a retail store to pay the rent, a friend and colleague who had moved to CAA Travel told me about an opening at their head office in downtown Toronto (since moved to Markham). There, I really started my career. I was able to give up the part-time job!

“I was with CAA for around 10 years, moving from travel agent to the training and support department to marketing and my last stop, branch manager. I have fond memories of this time as it was here I got married, had two children, went back to school and earned my certificate in adult education/facilitation.

“Soon after I joined Signature Vacations as Senior Inside Sales Coordinator. I loved my time at Signature Vacations. Similar to CAA, I was provided with the opportunity to change roles progressively and over the next almost 10 years, I was the manager of agency sales (reservations), BDM, manager of sales, director of sales – Ontario & Atlantic Canada. I was later asked to move over to SellOff Vacations. I earned my certificate in Executive Sales from Schulich School of Business during this tenure.

“Like all good mergers, in 2009, Sunwing Travel Group purchased a controlling interest in First Choice Canada. Seeing the need to control my fate, I started with what was then known as Mondial Assistance (now Allianz) as Director of Sales, Canada. Later I did a stint with iTravel2000 as Senior Director, Sales/Operations and Offline Marketing. And for two years, I worked with Expedia Affiliate Network (EAN).

“When CAA was hiring for a Director of Travel and Retail Product, I jumped at the chance and felt like I went home. So many familiar faces. I will forever be grateful for the people at CAA, as it was here when I was diagnosed and lived through the treatment for breast cancer. I could not have asked for a more supportive company behind me while that was going on, from the CEO to my direct manager (CMO) to my peers and my teams — thank you, CAA.

“In 2019, after H.I.S acquired Red Label Vacations, I joined the team as VP Retail (redtag.ca, iTravel2000 and The Travel Experts, i.e. their IC program). I had huge shoes to fill, with Joe and Enzo DeMarinis gone, but the team was so supportive and a joy to work with. All the previous jobs and experiences I had, from sales, call centre operations, marketing, training, and strategic planning, all of it was put to use in this role. I loved every minute of being part of this team. I hope they feel the same when I say I would still be there if COVID-19 had not happened.

“Of course, everything happens for a reason, and after taking the year off during COVID, I launched Reps4Rent.  A network of independent sales reps across Canada filling in for companies as brand ambassadors and salespeople when needed. The company is doing very well as it really is unique in that is project-based, not requiring any long-term contracts.

“Now, fast forward another year: I have passed on a successful business to my daughter and am beyond thrilled to be moving to my next chapter at Transat Distribution.

“When I look back on my career, this is a great fit for me because of the opportunity to do what has always made me most happy: to be part of a bigger corporation where tour operations and retail agencies live under one brand.  My unique experience as a franchisee will assist me as I work with Marlin Travel Agency owners and Affiliate owners.”
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Travelweek: What did you love about being a travel agent?

Jackson: “I loved my clients. I went into the business because as my mother was near the end of her battle with breast cancer, my father took her to Hawaii. I saw new life in my mother when she came back.  Every time, I did a trip for someone, I always had a little smile as I thought of my mother.

“And of course, I loved the opportunity to travel. Many of my roles after have more been ‘the business’ side of travel. As an agent, it is so important you take full advantage of fams. It is that expertise your clients want.”

Jackson and other members of the Healthy Hooters team at the CIBC Run for the Cure

Travelweek: You were with Signature Vacations for just about a decade in the late 1990s and early 2000s, before it was acquired by Sunwing. What memories do you have of working at that much-loved industry brand? 

Jackson: “The people (the same thing for almost all of my jobs). I have a relatively close circle of friends and quite of few of them are from my Siganture days. Back then the product launches were amazing – we always had one for employees first, then the trade. The pride we all took in our brand was amazing. I have no doubt that is the world I am going into with TDC / Transat Group. I realized in this job, I am a sales person – retail sales or tour operator , I am a sales person.”

Jackson in India with Anna Tarkowski Lorraine Brisbois

Travelweek: Do you think the retail travel industry is stronger now as it was back when you were starting out, or not as strong?

Jackson: “I think the retail landscape is definitely much smaller, but with that the quality of the agents is superior than years gone past. I feel that agents today have pride in what they do and most of all believe in the service they offer! They are one of the most passionate groups of people in this industry.”

Just a few of the reps in Reps4Rent, founded by Dianne Jackson and now run by Cassandra Jackson

Travelweek: What are you most excited about in your brand new role at TDC?

Jackson: “In my first few meetings, I asked people how long they had been with the TDC. I was floored by the length of tenure – 10 years would be on the low end. That says so much about a brand.

“I also am really looking forward to working with the franchisees and affiliates. Both of these relationships are unique. I want to learn from them what is important and support them in their growth and success.”

Jackson in Ireland with Deana Murphy

TDC’s website is TransatTravel.com. In the weeks to come watch for more interviews and memories marking Travelweek’s 50th anniversary. Plus, try your luck with our contest, ‘It Happened This Week’, featuring a new headline (and a new chance to win!) every Wednesday from Travelweek’s 50 years of travel industry news coverage.