Interview: Glenn Le Santo – When A Pirate Joins the Navy.

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When maverick social media buccaneer Glenn Le Santo joined Orange’s corporate battleship, it wasn’t all plain sailing – but he soon caught a favourable wind

This is one of a series of interviews leading up to Like Minds, Bristol – powered by Barclays  which takes place on September 8th & 9th. You can learn more about the event and book tickets here.

There’s a classic encounter in Pirates of the Caribbean when the craggy Captain Barbossa responds to his privileged, well-spoken captive Elizabeth by putting her in her place: “There are a lot of long words in there, Miss – we’re naught but humble pirates.”

An unforgiving maverick roped to the poop of the Black Pearl, Barbossa embodies the world-weary, straight-talking buccaneer who neither minces his words nor defers to petty formality.

Marketing, like piracy, can thrive on mavericks like Barbossa – and it has its very own in Glenn Le Santo, himself the ancestor of a Spanish privateer imprisoned in Plymouth whose son fell head over heels for a Devonshire milkmaid.

Le Santo, the head of International Social Media and Blogging at Orange Business Services (OBS), is a rare beast: a pirate who has joined the navy, so to speak, swapping the metaphorical Black Pearl on which he long navigated a successful freelance voyage for a corporate battleship.

“When Orange asked me to join them and I said yes, it surprised a lot of people because I’m very much a free spirit, I don’t work well in an office environment. I’ve got a boat and like to work from it, I like to play loud music while I’m working – none of this is compatible, you would have thought, with the corporate life.”

Le Santo invoked his pirate legacy in the personal brand that he developed as an early adopter and pioneer of digital and social media after a varied and exciting career as a journalist covering, among other things, the high-octane world of motorcycle racing.

“People related to it: I kind of fitted the bill, I’m a little off the cuff, I speak my mind sometimes when I shouldn’t, I’m very direct, and I’m quite alternative. So I said to Orange: ‘You are employing the pirate, you do realise that don’t you?’, and they said ‘That’s exactly what we want’.

“The manager who employed me was being very brave: she was injecting into her department something that was completely missing, which was a non-compliant, creative maverick.”

Inevitably, however, this transition has involved a steep learning curve for Le Santo, but one that he soon realised not only benefited the big brand – a key revelation was that the life of the freelancer is not quite as “free” as it might seem, and that the corporate world offered real creative possibilities.

“I think people probably expect me to say it is really hard to get things done in a corporate environment because you need to get things agreed, signed off, and stuff like that,” he says.

“And at times it is true that the stultifying pace of corporate progression can be frustrating. But let’s face it, when you are a freelancer you rarely get the kind of freedom to do what you want anyway because you are working to a brief and you are terrified that if you don’t completely match the customer’s expectations you’re not going to get the job again.

“It’s a balance: you have got a basket of worries as a freelancer that weighs the same as the basket of worries you have as a corporate person. So the lesson I have learned is patience.”

An experienced writer with tech skills who moved into the world of marketing just as the social media revolution was unfolding – he was the first journalist to officially live tweet from a FTSE100 company’s quarterly financial briefings – Le Santo says he has learned much from joining Orange two years ago.

“I really take my hat off to Orange they have been unbelievably accommodating. My immediate manager in particular has been absolutely fantastic – she has fought battles for me and facilitated my cranky weird way of working. And it’s give and take: I’ve not been as fierce and piratey as I used to be. I have learnt diplomacy and I’m really quite proud of that: how to be a really good diplomat and how to reserve the pirate for when I really need him.”

The immediate difference Le Santo became aware of when he threw in his hat with the corporate crew is complexity.

“It wasn’t an easy transition; the first three months were a mixture of heaven and hell. One of the biggest differences between being a freelancer and working on the inside of a large corporate body like Orange is complexity: I am a cog in a machine and need to make sure I turn with all the other cogs, which can be quite difficult if you are a maverick.”

Outspoken and, after many years as a freelancer, used to doing things his own way, Le Santo says the first tip for survival is: “leave your ego at the door and learn tact”.

In order to get on, he adds, it also helps to be “nice”, something he says that coincides with the prevailing culture at OBS.

It is a great advantage, he admits, that his branch of Orange is dedicated to promoting tele-working, enabling him to work from his beloved boat – and a good example of how forward-thinking employers can gain a real commercial advantage.

“This approach really works,” he says. “We are at a pivotal point where it’s no longer about companies saying ‘You must work this way’ but saying ‘How can we get the best out of you?’

“If I wanted to sit at the top of Nelson’s Column in a pink dress writing my social media updates and that was the way it worked best, then they should damn well let me do that. I don’t, fortunately: I’m not great at heights and I don’t look good in a pink dress.

“But companies need to be that flexible and, if their systems don’t allow it, to change their systems – because it’s not the worker that’s wrong, it’s your system that’s wrong.”

To hear more on this from our stellar line up of speakers, come and join us at the Like Minds, Bristol, “Innovation & Ideas Festival” – powered by Barclays on September 8th & 9th. Read more and book tickets here.

About the author

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Gavin O'Toole is Consultant, Head of Research at Onyx and a journalist, author and copywriter with a specialism in finance and business.