Big Interview: Richard Singer, chief executive of

The chief executive of the holiday metasearch and deals publisher tells Lucy Huxley about his first six months in the job

When Richard Singer accepted an offer to become managing director of Monarch Holidays in August 2017, he had no idea it would collapse before he had even started in his new role.

He had left travel deals publisher Travelzoo, where he had climbed the ranks over five years to become president of Europe and Australia, having previously worked at the Telegraph Media Group running the travel division.

Luckily, plenty of companies were keen to snap him up and he received offers from established operators, OTAs and even tech firms outside of travel.

Singer, however, chose to join, the Leeds-based holiday metasearch and deals publisher, which is backed by private equity firm Palatine. And he hasn’t eased in gently. In just five months, Singer has made significant changes to the strategy, team and culture.

“I very quickly realised that I could make a positive impact to the icelolly business,” he said.

“I was also motivated to work in a private equity environment. Over a whirlwind few days I met with Palatine and decided this was the right next step for me. Icelolly was already a significant brand, there was some great talent within the team and the business had recently launched a new holiday comparison marketplace. I was genuinely impressed with the transition under way”.

While previous chief executive Andrew Latham was recognised for setting the foundations of the business transition, there was much work still to be done.


The first challenge facing Singer was to communicate the value that icelolly could deliver to its advertiser partners following its relaunch at the turn of the year. Brands featured on now include Tui, Thomas Cook, On the Beach, Love Holidays and Travel Republic. It also has budding new relationships with cruise lines, airlines, tourist boards and DMCs, many of which maybe hadn’t previously considered icelolly a viable distribution channel.

In his first five months, Singer claims to have met and presented to more than 50 potential advertisers, racking up 5,000 miles of flight and train journeys, which has been challenging given the arrival of a new addition to the Singer family in February. He said: “It’s been tiring but also hugely rewarding to speak to so many businesses and to understand each of their challenges. My wife is just about still talking to me!”

Sales team

Singer has recently announced the recruitment of an “all-star” sales team led by Stuart Barrett, also formerly of Travelzoo, in the new role of sales director.

“Stuart knows the industry inside out and he and his new team, which includes people from Expedia and Kayak, have the right balance of experience and expertise”.

More recruitment is planned as Singer seeks to develop icelolly’s deals business. “I know the deals space well from my Telegraph and Travelzoo experience. We’re looking at a number of candidates to support the fantastic work of the existing team.”

Repeat users

Singer is keen to stress that since icelolly relaunched its comparison marketplace in December 2017, it has seen its customer satisfaction measures improve significantly.

“Our Net Promoter Score has improved 33% to 55 points over the first quarter of 2018 and we’ve tracked a -85% reduction in customer complaints, mainly related to the inclusion of household brands that provide reassurance and familiarity, and improved accuracy of our pricing.”


Singer is keen to highlight that icelolly won’t simply become a ‘me too’ metasearch brand and new technology product development is high on icelolly’s priorities list.

“We feel differentiating the search-and-compare experience we present to our users is key and we’ve ambitious plans in this area. Other metasearch sites have some really neat tools, such as price alerts, mapping and fare calendars, but these are confined to either flights or hotels right now. I obviously can’t say a huge amount today but we’re pressing forward in developing planning tools for our users to complement the pricing and availability results that will ultimately help to save our users’ time and money when planning their holidays. One of the most enjoyable elements of working in private equity is the pace and speed we are able to invest and launch these products.”


One proposal is to look at how icelolly could help its users find local travel agents.

“More of our users are asking us about experiences and also increasingly complex travel plans that include cruise or touring,” said Singer. “Combine this with the fact that nearly 70% of our users visit from mobile devices and we think there is a great opportunity to help agents on the high street connect with metasearch, something out of reach for those agents today.”

Icelolly is also looking to widen its product mix from largely short-haul beach to a broader selection of holiday types, including cruise, long-haul, villas and UK breaks.


Singer is clearly confident about icelolly’s prospects and believes the combination of a growing package holiday market, strong management team, proprietary marketplace technology and the icelolly is an exciting mix.

“Our brand punches above its weight, with great awareness. Most recently we sponsored ITV’s The Keith & Paddy Picture Show.”


When asked what he is most looking forward to over the coming months, Singer said: “The business feels like a start-up right now. We are the underdog, vying with many competitors for travel audiences. I’m excited about our team, our ideas and our agility.

“I’m looking forward to growing icelolly into a top-10 UK travel brand and beyond.”

60 seconds with Richard

What’s the last book you read?
A signed copy of Dead Men’s Trousers by Irvine Welsh.

Where is your favourite holiday destination?
The French Alps in the summer.

What’s your guilty pleasure?
Butterscotch Angel Delight!

What’s been your best experience working in travel?
I have been fortunate to have had the opportunity of running businesses outside of the UK. I have made some great, long-term friends, all over the world.

What one thing about the industry would you change?
This is more a bugbear about flying – namely, being the last to board and finding the luggage bins are full. Your bag ends up 10 rows behind you or, worse, you hear the words of doom: ‘This will have to go in the hold.’ Surely some clever people can solve this irritation.

Which three people in travel would you invite to dinner?
Chris Loughlin, ex-CEO of Travelzoo, an entrepreneur and one of the most dynamic people I have worked for. Philip Wolf, founder of Phocuswright and probably the most-connected man in global travel. And Michael Wright of Riviera, a man of great integrity.

Which three people NOT in travel would you invite?
Willie Miller, Gordon Strachan and Eric Black, who were in the Aberdeen team that defeated Real Madrid to win the 1983 European Cup Winners’ Cup.

Which song reminds you of holidays?
Greece 2000 by Three Drives.

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