A FORCE FOR GOOD hub | Alex O’Connor’s Inspiring Story, Make a Dent in the world
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Alex O’Connor’s Inspiring Story, Make a Dent in the world

Alex O’Connor – Managing Director – Insight Vacations

Make a DENT in the WORLD

Any woman who takes two months off to lead a team of students as they help rebuild a school in an underprivileged region of Costa Rica and who also possesses the determination to run the New York Marathon is an inspiring leader in JC’s eyes.

Enter Alex O’Connor, managing director of Insight Vacations – a woman who is determined to make a dent in the world.


Growing up in New Zealand, Alex dreamed of being a foreign correspondent in a far-flung location. “I always had a fascination with what was going on in the world,” she tells JC. Geography was her favourite subject in high school. She briefly dabbled in law because she felt it was something she “should do”, but unable to deny her original passion for geography, she ended up doing a master’s degree in the subject.

Alex’s next step was to snare a place on Air New Zealand’s now-defunct graduate management program in the face of stiff competition from hundreds of highly qualified people. She’s convinced her broad set of interests and curiosity in the world are what got her across the finish line. “That was my first job in travel and I really never looked back from there,” she says. “I felt so lucky I got that break – joining the national airline straight out of university was a dream job.”

Investment IN TRAVEL is an Investment IN YOURSELF

The program gave Alex six month’s experience in the strategy team, followed by similar stints in marketing and direct sales. “At the end of the program, I did what any good Kiwi or Aussie would have done – I said thank you very much, packed up my bags and moved to London for two years,” she says. “Of course, I later returned to Air NZ but at the time I had itchy feet to get out and explore the world.” In London, Alex took on a few different sales roles in travel management companies but used any opportunity to hop on a Ryanair or Easyjet flight to see as much of Europe as possible.


When the time came for Alex to leave London, she still wasn’t really ready to return home. She had been studying Spanish for a few years so she decided to put those language skills to good use by heading for Chile. Over the course of the next year, she taught English, worked on her Spanish and travelled through South America. “Yeah, I had a great time – I put real life on hold for a year,” she says. “I would say to anyone considering doing that, yes – go and do it, you don’t get that many opportunities so you need to grab them.”

Sure, there were a few things playing on Alex’s mind. By now she was in her late twenties, she had spent every last cent of her savings on travel, and had an underlying feeling that she should kick-start her career. “But I knew a year wasn’t going to make a difference and I really wanted to do this,” she recalls. “In hindsight, what actually happens is that you learn an incredible range of skills like resilience, adaptability and perseverance – all those things you learn when you are living in a country where you don’t speak the language.”

Alex says her experience was as “enriching and educational”, if not more so, as working in an office role. Rather than setting her back, she believes it actually drove her forwards.


Eventually, it was time to head back to New Zealand. On her return, Alex briefly took on a Flight Centre role before making her way back to Air New Zealand where she stayed for five more years.

But it wasn’t the end of Alex’s globe-trotting adventures. Taking three months off from her job in the middle of the Global Financial Crisis, she headed for rural Costa Rica where she spent two months working with a British organisation called Raleigh to build a school from scratch. Leading a team of 20 young people, Alex ditched wifi, sleeping on a wooden platform in the Costa Rican jungle as together they built the school.

“It was an eye-opener for everyone,” she remembers. “The contentment of the locals with such simple things really put into perspective what you truly need to make you happy.”

The experience was “very fulfilling” and she is so thankful to have been a part of the project, made possible by the support of Air New Zealand. “So often people presume that employers are just going to say no, but if you work hard and are a valuable worker, just ask for those opportunities,” Alex urges. “Particularly while you are young and you’re learning, you’d be surprised at how supportive organisations are to allow you to do that, because it’s valuable for them as well in terms of building your learning and leadership skills.”

ALEX O’CONNOR making a difference Jito Connected inspiring sotries

We ARE ALL CAPABLE of amazing things

But Alex still had another achievement she wanted to add to her list – a marathon. It wasn’t however until she turned 30 that she decided to take the plunge. “I’m not fast but I am determined and I think the marathon really suited my temperament,” she explains. “It’s about planning, training and not giving up.” After the first one, she “got the bug” and so ran another two. “It’s such a personal endeavour,” she reflects. “It’s quite moving because you see people running for all different kinds of reasons, testing themselves. They are not running against anyone else, they are just pushing their own limits.”

When Alex looks back at her career, she considers her time in Chile, the school building project in Costa Rica and her three marathons as “valuable learning experiences that I wouldn’t have got in an office environment”. “Steve Jobs said it well,” she says. “He said, ‘You can’t always connect the dots forward, but you can connect them backwards’.”

Forgo the COMFORT ZONE and take a big JUMP

Despite a great stint with Air New Zealand, Sydney was calling. Having worked with the team at Virgin Australia through her work at Air NZ, when a position came up at the Australian carrier, it seemed like a great move. “Virgin was at the beginning of its journey so it seemed like an exciting opportunity to take on a bigger market,” she says.

From there, Alex made the exciting move to head up Insight Vacations as managing director earlier 2016 – a position she is thoroughly enjoying. “I’ll tell you the thing I’m loving at the moment, what gets me through a long day, is going to listen in on the phone conversations with our customers,” she reveals.

“Our customers are so inspiring. They might be celebrating a 40th wedding anniversary or they’re going back to Paris for the first time since they were in their 20’s, they’ve brought up families, paid off mortgages, worked hard and now is their time to live it up – it’s great fun to be able to help them to do that.”

Be TRUE to yourself

The team is all-important for Alex too. One of the big things she says she has learnt over the years is not to hire people that you wouldn’t want to sit next to at a dinner party all night. “You spend a lot of time at work, so while it goes without saying that they need the skills and the competencies to do the job, you also need that chemistry in a team where people are prepared to put in discretionary effort – and that comes from feeling a sense of connection and accountability to your team mates,” she says.

Feeling comfortable within herself has, without a doubt, been key to Alex’s success. “When I was younger, I had this vision or an image of what a corporate person should be like and how they would portray themselves and I would try to act like that,” she says. “But I think that as you go on in your career, being true to yourself and understanding your strengths but also letting people see your vulnerabilities and weaknesses actually makes you more real and relatable as a person.”

“It’s a lot easier and more effective to be your own person than to try to mimic someone else’s style and so it’s nice to be at that point.”

Here is ALEX’S ADVICE for young people looking to get ahead in their career…

Work hard and earn your stripes in your current role before looking to move on. The best indicator of someone’s future potential is what they are delivering right here, right now.

Take risks. Don’t be too afraid to jump roles or organisations when you feel your learning curve taper off.

Aim high. As my Dad  used to say – if you’re not a little anxious about the role you’re about to take on, then it’s not a big enough jump.

Be true to yourself and be real… understand your strengths but also let people see your vulnerabilities and weaknesses. It makes you more relatable and gives other people licence to be themselves as well. 

Don’t take it too seriously. At the end of the day, it’s a big game and we may as well have fun along the way.



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