Becoming the country manager of Dropbox Australia and New Zealand was not necessarily always on Charlie Wood's mind, nor was working for Microsoft and becoming the vice president of Salesforce Asia-Pacific. Rather, the only thing on his mind when growing up was becoming a pilot.
"I always thought I wanted to be a pilot, and said to myself, 'I'm going to be a pilot, I'm going to be a pilot'," he said, explaining that during his time as a paper-delivery boy in his English hometown of Stockport, he would often watch planes fly over while he was on his push bike.
Wood's determination to become a pilot found him cheekily joining Microsoft during his early 20s so that the company would pay for his flying lessons.
"I really got into the tech space to pay for flying," he admitted.
Wood, however, wasn't completely out of the technology loop. During his younger days, he found himself owning a Sinclair ZX81, one of the very first computers that hit the market, and he would code his own games and software. He explored this interest further in university by taking up a software engineering and statistics degree.
But his dream of becoming a pilot quickly became a distant memory when Wood took his then-girlfriend -- now wife -- out for a weekend getaway in a plane, before they were forced to make an emergency landing in a pig farm in Nantwich because the planed "packed up".
"[The emergency landing] put me off a little bit. It was a good newspaper headline, though: 'Pig farmer's field saves pilot's bacon'. We have a photograph of this little plane sitting in front of the farmhouse, where a plane should not have been."
Following the mishap, Wood chose to stay in tech, but that didn't impede his sense of adventure. Wood's decision to stay on with Microsoft enabled him to benefit from 10 years of having the opportunity to combine work with travel, when he moved from the UK to New Zealand, and then to Seattle.
"Microsoft was really interesting. It was obviously going through a lot towards the end of the '90s, early 2000s. Because it was a great phase for Microsoft, that enabled me to have some really interesting roles from consulting and managing that side of the business, then on the more technical side of product management, and then running channels and partners," he said.
"It took me to places, and it's a company that really looks after its employees from a training point of view."
At one point, prior to moving to Seattle, Wood even had the ability to take a gap year. He confessed that it had been his opportunity to take one last dangerous trip before kids arrived.
"I took a year off completely from work whilst I was living in New Zealand. Me and my silly mates sailed a small boat to Antarctica. We used it as a base for a skiing/mountaineering expedition. I trained for that in the southern alps of New Zealand for the entire New Zealand winter," he said.
"I spent time there climbing around the Mount Cook region and along the glaciers, then we basically climbed up things and skied down them, and we did that for three months. Then we sailed to Antarctica and did the same thing there."
He rejoined Microsoft following his travel stint, after realising that somebody in his household needed a job -- and that it wasn't going to be his wife, their first newborn, or the dog.
"They were all looking at me. So I rejoined Microsoft and we moved to Seattle, which was great. I was responsible for taking Dynamics CRM to the cloud," he said.
While the corporate life with Microsoft had its benefits, Wood said at that point, he needed a lifestyle change, and the appeal of Sydney's Northern Beaches was indisputable.
"We've always fancied the Northern Beaches lifestyle, and the whole surf life-saving lifestyle. We thought having two boys and a girl, there'd be nothing more fun than to grow up there," he said.
"I grew up in the north of England, which was pretty miserable, where the sun doesn't shine at all. I thought what a great life it would be for us if we could do that, so we moved over here and bought a place."
To mark the change in lifestyle, Wood kickstarted his own company, Social2CRM, a social media monitoring and CRM consulting company, which he said grew very quickly, reached a million-dollar run rate, and serviced customers including Dell, Microsoft, Lockheed Martin, and RightNow.
"It was a definite decision to avoid corporate for a while and to build something. I thought I had a good idea and wanted to make something of it," he said.
To keep the relaxed nature of the Northern Beaches in Social2CRM, Wood chose not to have an office, and decided to employ a close-knit team made up of parents who were living in the same area, had young kids, and were after some work.
"If you go up to Avalon, you can barely swing an organic baguette without hitting a media director who is taking a career break. I thought this is a perfect market of who we were selling to. So we employed a bunch of kindie mums and they were all friends of the neighbourhood, but they were also like 10-year account directors, or a creative director of Ogilvy."
But about halfway through, the company changed tack when it started working with social media monitoring firm Radian6, which eventually acquired Social2CRM, explained Wood. He said it was timely, given the changing nature of the social media market at the time.
"We went from a small team up in the Northern Beaches, and we quickly grew to 40 people around Sydney, Melbourne, Singapore, and Tokyo. Those growth trajectories were really quite impressive; we were growing in triple digits."
According to Wood, he learned to view the acquisition from a positive perspective thanks to his "unofficial mentor" and friend, Gareth Thomas, who said: "Whenever there is a gold rush, you're better off selling donkeys and shovels than panning for gold".
"He's an English fella who lives out in the Hunter Valley, and is a publisher and a real entrepreneur. He gave me the best piece of advice I've ever been given, and he claims he never gave it to me, which is even better! He says he's never heard it before but I'm pretty sure it was him," he said.
"It's a story about scarcity, and I think if there's anything I've ever learned, you've either got scarcity or scale for any business to be viable and successful."
Eventually, Radian6 was acquired by Salesforce, which gave Wood the chance to get back into working with a larger company: As vice president of Asia-Pacific for Salesforce.
"It was just about putting the corporate trousers back on," he said.
But after three and a half years with Salesforce, Wood decided to join Dropbox last September.
"I've jumped between big and small. Dropbox is just in between; it's not big or small, but it's going to get big. It's this growth phase that I really enjoy, and I enjoyed it while I was inside of Salesforce," he said.
"When the opportunity came up to talk to [Dropbox], it was just the perfect phase for me. I like building the team, hiring the team, and I've got familiar faces coming in, and a lot of new faces."
Wood, who has only been with Dropbox for six months, said he plans to see through growing the company in Australia.
"I want to see this business through for as long as I can. This is a very good business, and the team we're building here is world class. I have four new people, a couple more next week, directionally we'll be about 50 by the end of the year. Then we'll continue to build this team, and then we'll figure out what's next," he said.
"What's interesting for me here is that things are changing rapidly, and it will look very different in 12 months' time."
Wood admitted, though, that he still needs to learn how to focus on one thing at a time.
"I really got into the tech space to pay for flying."
"Because of my breadth of skills, I have a tendency to focus on too many things at once. A good example is that the week that has just gone, I was writing papers and marketing materials, while having meetings and analyst calls, and then figuring out how to reconfigure the CRM system for the sales team," he said.
"Every now and again, I need to remind myself to back up and let somebody else do it, and focus on the key things I need to do as a manager. That has been a challenge for me to keep focus on the key things, and keep out of the some of the little rat holes you can get into."
While Wood continues to remain professionally challenged, he also retains the spirit of an avid traveller. He recently returned from a trip to the Himalayas with his eldest son.
"We were involved in the Himalayan Development Foundation of Australia. It was co-founded by a good friend of mine, Duncan Chessell, who I've climbed a lot with in the Himalayas, and he's climbed Everest five times, and done the seven summits.
"The reason why I took Felix on this trip was, one to raise some money for this Sherpa village, but also to remind him that not everybody gets a new mountain bike when they want one, or the infinite gelato machine at the local shop.
"We went hiking in the high Himalayas, living in tents, hanging out with yaks and Sherpas, and he spent time at the Sherpa school, which was almost medieval in the way it looked; there was no electricity, running water was from a tap down at the end of the road."
Wood has also already planned for his next adventure, but is unsure, as yet, when to take it.
"At some point, I keep threatening my wife we're going to take the kids out of school and sail around the world for a year. I'm not sure when that's going to happen, but that's the plan."