Simon Hagger

CEO Shortbreaks Ltd (deputy CEO Holiday Extras Group)

Simon joined Holiday Extras as the first ever graduate trainee back in 1996 and worked his way around the business working up to various management roles; hotel contracts manager, head of commercial, head of call centre and holiday insurance operations among them.

Simon's role as head of New Ventures led to a position on the executive board of directors as New Business Director in September 2006. After the successful launch of a new Short Breaks division Simon became CEO of the Short Breaks business in December 2009, in 2014 he joined the Group Board and in 2015 he was also appointed to the role of Deputy Group CEO to the Holiday Extras Group.

The Short Breaks business specialises in breaks to UK theme parks, visitor attractions and London theatre. The division now employs a permanent team of 150 in a dedicated facility at Apple Barn, Smeeth.

Simon's team is now principal operator of the official short breaks for Merlin Entertainments Group in the UK (LEGOLAND Windsor, Alton Towers, Thorpe Park, Chessington World of Adventures & Warwick Castle). In addition to working with Merlin Entertainments Group, Simon’s team also operates the official short breaks programmes for Paultons Park and The Ambassador Theatre Group in London.

Simon picked up Travolution's Rising Star of the Year award in 2010 for his work in setting up the Short Breaks division and innovating in other areas in the online space, including being co-founder of a mobile first learner driving market place (a bit of a side project that took off rather well!).

He has increasingly found his responsibility expanding into the e-commerce and digital space as well as commercial and operational leadership; making Simon a good choice to support Matthew Pack as his Deputy across the Holiday Extras Group.

Life before Holiday Extras

Simon's degree in Geography from the University of London inspired his passions for travelling the world and a career in the travel industry. After seeing Australia, New Zealand, Indonesia, the USA, Canada and Thailand, and flirting with a career in personal fitness training in Sydney, Simon headed back to the UK and>

Life apart from work

Simon has a love of walking in the countryside with his dogs, photography, swimming (sometimes in the sea!), paddle boarding and renovating his house and garden - including a new found passion for some fairly amateur carpentry! ...but mostly enjoys time and activities with his family. Simon is married with two daughters. Simon is also a Governor at Stowting Primary School.

What's your perfect hassle-free holiday?

Can I have two?! A simple UK camping trip with my family, fresh air, free reign and fun for the kids, being outside dawn 'till dusk. If there's no smart phone service - even better but I might sneak to the top of a nearby hill to get service and check my emails on occasion!

On the other hand, I recently spent four nights in a lovely boutique hotel in rural Spain near Ronda, to celebrate our 15th wedding anniversary. That was perfect too, peaceful and full of delicious local food and wine.


I love super creative and ambitious people who take an idea and make it a reality, being passionate enough to roll with the knocks and keep going. I admire the tenacity shown by the British troops return injured from operations but despite devastating injuries pick themselves up and get on with life, often going on to achieve even greater sporting, career, social and family success.

And my kids - the way they view the whole world with complete wonder, possibility, optimism, opportunity and happiness. It's something we need to work hard to maintain as we grow up - I think these traits make for the best entrepreneurs too!