Gillings is one of Great Britain's realistic medal chances for next year's Winter Olympics in Sochi, where she is on course to make her third Games appearance after ranking 15th in 2006 and eighth four years later in Vancouver.
However, not content with taking on the might of Canada's all-powerful snowboarding team - including defending Olympic champion Maelle Ricker and X-Games winner Dominique Maltais - Gillings also has her sights set on emulating discount website GroupOn.
When her national governing body experienced a funding crisis, the 28-year old founded her own business, the Isle of Deals, which aims to give residents of her native Isle of Man the inside track on the best offers around.
Want a Swarovski Elements Crystal heart for an 80% discount? Gillings knows the right guy.
Fancy a romantic dinner for two and night at a top hotel in Douglas? Then she can negotiate a half-price deal and throw in breakfast.
And Gillings - now back on funding after the formation of British Ski and Snowboard, following the Vancouver Games - insists the off piste distraction is both profitable and valuable to her Olympic ambition.
"After I lost funding I knew I had to take my fortunes into my own hands. I needed to think totally outside the box to make some money, just so I could continue in the sport and doing what I love," she said.
"I've got my lottery funding back now and we've got a really stable governing body in place, so I'm in a totally different position to the build-up to Vancouver.
"However, I really enjoy working on the business and, with my laptop, I can run it from anywhere in the world. However, I use every penny I make on my snowboarding, I'm not a dot.com millionaire I promise you.
"It also really helps have something apart from sport to think about, I don't think it's good for you to become too tunnel visioned. I'm a great believer in having a back-up plan, this is an unpredictable sport so the business is there should anything go wrong."
Gillings' 'out of the box' thinking recently lead her to install a start gate in her back garden in Leeds to prepare for Sochi. She has already ticked off the first selection criteria with her performances last season and needs to maintain a world top 24 ranking - she is currently eighth - by next January to secure her slot.
"It's not a case of third time lucky because I'd like to be still involved in four years," she added.
"Statistically, if you look at the medallists at the last two Olympics they are around the early 30s age. Because it's a new sport, we are only just starting to figure out what age you can go on to and peak at.
"The longer you can look after your body and stay injury-free then experience plays more of a role in snowboard cross than any other snowboarding discipline."
Gillings ranked 11th in the Olympic test event in Sochi this February and will be using the forthcoming World Cup season - starting in Montafon, Austria in December - to fine hone her skills ahead of her event on February 16th at Rosa Khutor.
"Every year the standard increases, the courses are tougher and even more technical," she said.
"I'm confident, it will be about maintaining that confidence through the World Cups and getting to Sochi in good shape."
© Sportsbeat 2013