TORONTO — For Denise Heffron, landing her dream job wasn’t all it was cracked up to be.

The travel industry veteran, who currently serves as Managing Director-Commercial at Uplift, graduated from Western University in 1989 with an English degree, which she promptly put to good use at the Ministry of Education, writing and designing correspondence booklets for students unable to attend school. 

Transat’s 30th anniversary with Nancy Jackson, 2018

By all accounts, this was an ideal first job for the newly graduated Heffron. But was it exciting and fulfilling? Not so much. So when her best friend, Nancy Jackson, who was working as a sales rep for Sunquest at the time, invited her to a product launch, Heffron gladly accepted. It was there while helping to unpack and pack up the Sunquest booth that Heffron first realized work could actually be fun.

“It was eye opening, and I wanted in on the action. So the next day I asked Nancy to help get me a job and she did. I am so grateful as I now am truly passionate about travelling and our industry, both of which have enriched my life in immeasurable ways.”

After spending a year at Sunquest designing brochures and fliers, Heffron moved to Transat in 1993, which would become her “home and family” for the next 25 years. There, she held a number of marketing and commercial roles on the tour operator side of the business before eventually retiring in 2018 as VP National Sales and Commercial. Just three months later, she joined the team at Uplift, a fintech company that enables travel providers to offer installment payments to their customers. In July 2023, news broke that Uplift was acquired by Upgrade, Inc. for $100 million.

It’s now 30 years and counting in the travel industry for Heffron, who long ago had dreams of being a professional writer. Does she have any regrets about not going down the literary path?

“Not at all, life is too short for regrets,” she says. “I may still pursue writing one day but if I do, I will definitely be a travel writer. I can think of nothing better to write about.”

In this latest instalment of Travelweek’s Interview series, launched in celebration of our 50th anniversary, we sit down with Heffron to discuss the various challenges she’s overcome in her career, the mentors who took her under their wing, and the life-changing lessons she’s learned along the way.

What are some of your fondest memories that you have from your early days in your travel career?

“My early days in travel consisted of speed, adrenaline, pressure, laughs, tears and, at times, sheer panic. It can be a tough business when you know what you’re doing, and I certainly had much to learn. I was an artsy academic in those days, and prior to my government role I worked for two English professors so I was used to a very different culture, one that was quiet, thoughtful, measured and solitary. 

“But I soon came to understand that travel is a real and meaningful community where colleagues and friends are one and the same. It’s one of the many reasons why I love the industry so much – my work mates from way back in ’93 are still very good friends and business partners, and many of the Transat gang are like family. And through it all, Nancy is still my best friend today!”

Uplift Canada team with Ian Citulsky, Tanya Johnson, Stuart Morris and Kelly Tyndall, 2022

Do you remember your first work trip or FAM trip? 

“My first work trip was most definitely Montreal. As for my first FAM trip, it’s a bit blurry but I think it was Cuba with Transat, to Farallon del Caribe. One day, we went to a private island, had drinks and lunch on the beach with no one around for miles – just crystal clear waters, beautiful weather and great company. I remember sitting in the ocean with a rum punch – Havana Club, no doubt – and thinking how lucky I was. I also loved seeing all the hotels on those early FAMS (I still love a good hotel inspection), but mostly I remember the camaraderie and good times. I also remember being very, very tired after FAMS!”

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Did you have a mentor during your early days? If so, what did they teach you and how did you apply those lessons in your career down the road?

“I’ve had the opportunity to work with some true travel legends, but the clear standout from the early days is Paul Foster, VP of Transat at the time. He was generous with his knowledge and time, he taught me the foundations of the business, and he gave me and so many other young people in the industry opportunities. 

“Paul also knows how to enjoy life and we had a ton of fun. He remains a good friend and mentor, and to this day I seek his advice. Notably, he was the first to sign a contract with me when Uplift entered the Canada market, which was very meaningful.

“I could literally write a coffee table book of ‘Paulisms.’ On my first day at Transat, he told me ‘Mohammed goes to the mountain,’ or in other words, get yourself to Montreal and develop some relationships at head office. I got on a plane that first week and continued the back-and-forth throughout my entire time at Transat. It was great advice and served me well both professionally and personally. I have loads more ‘Paulisms’ where that came from, but you’ll have to wait for the coffee table book!”

Margarita Island FAM with Paul Foster and a tour guide, 1994

What are some challenges that existed in the industry in your early days that don’t exist today? And what challenges did not exist back then but are prevalent in the industry today?

“There were a lot of cowboys and not too many cowgirls in the early days, so I think the industry back then lacked an appropriate balance – though the strong women we did have were bonafide superstars. I have always believed that good balance of all sorts make for better output and good business.

“In addition, the manual nature of the early days was challenging, inefficient and error-inducing, things like pasting up brochures and ads, doing payload and costings with pencil and paper, using fax machines and so on. I remember we had an intercom system at Sunquest and I truly thought it was state of the art. Imagine being able to talk on the phone and page someone all at once! Fortunately, we now have all kinds of incredible technology to help us with our jobs. 

“In today’s world, the pandemic has created many challenges for the travel industry that are still being worked through – staffing is one. We not only need to staff for today but for tomorrow as well. It’s up to all of us to educate the workforce about the travel industry and its many interesting jobs, recruit talent, train, plan for succession, and provide opportunities for advancement.

“I also believe that the consolidation we have experienced in recent years has created some challenges and risks. What used to be many mid-size companies are now a handful of very large companies. The current debates regarding TICO and the Compensation Fund underscore this issue.”

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These past few years have taught us the importance of adapting. Can you give us an example of a time when you’ve had to adapt in order to thrive in your career?

“So many times over the years I found myself needing to pivot. In tour operation, I used to feel like the day-to-day running of the business was something we only had the luxury of doing between a myriad of crises, like hurricanes, ash clouds, 9/11, SARS, Zika, earthquakes and more. The ability to adapt and navigate the unexpected is critical in our business, for sure.

“I’d say the biggest adaptation for me personally was five years ago when I left tour operation and moved to Uplift, a travel-focused Fintech. For the second time in my life, I found myself in an industry I knew very little about. My current boss, Tom Botts, took a chance on me – much like how Paul Foster did many years prior at Transat, and Ron Harding, VP of Marketing at Sunquest before him. I knew the product would work well here but I had a lot to learn and found a wonderful mentor in Tom. Google was also a very good friend to me! The business, product, culture and even language was entirely different. I have learned so many new things and it was a great move for me at that point in my career. It has been very rewarding to take a product from inception to complete market coverage in only a few short years.”

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What’s your favourite thing about working at Uplift? And do you foresee any changes to your role now that the company has been bought by Upgrade?

“I have truly enjoyed having the ability to introduce a new business, product and brand into the market – it’s been a unique experience that I didn’t expect to have. But of course, I didn’t do this alone. I had so much help from the amazing team at Uplift, but also from my industry family. Former clients, competitors, employers and co-workers all showed their support and helped me along the way. Startup life is intense but I find myself with a very supportive group of professionals and friends who make every day enjoyable and educational.

“The Upgrade acquisition is still quite fresh but Upgrade has assured not only me, but the entire commercial team that no changes are planned for our roles. For our partners, this means it’s business as usual. I am very excited about the acquisition though – Upgrade has been extremely welcoming to us all and they have an amazing suite of products and an impressive team and track record. Responsible lending is a core ethos of Upgrade and that really resonates with me personally and aligns with the Uplift culture. Today, Upgrade is operating only in the U.S. but it is my hope that we can eventually bring their products to Canadians and that’s something I’d love to be a part of.”

Working the Transat booth with Susy Stafford and Loretta Palermo, 1993

Watch for more interviews and memories throughout 2023, marking Travelweek’s 50th anniversary this year. Plus, try your luck with our contest, ‘It Happened This Week’, featuring a new headline (and a new chance to win!) every Wednesday in Travelweek Daily, from Travelweek’s 50 years of travel industry news coverage.