Singer spent five years with the travel deals publisher before leaving to become managing director of Monarch Holidays earlier this year however the company collapsed in October before he began work.
Prior to his time at Travelzoo, he held positions with Telegraph Media Group, including general manager of Telegraph Travel.
Singer takes over from Andrew Latham, who left Icelolly after almost four years with the business.
Singer said: “I am delighted to be joining a dynamic and entrepreneurial business at such an exciting period. The Icelolly.com team has built a fantastic brand which serves as an important distribution platform for travel companies.
"I am looking forward to working with the team to promote the brand further and develop new propositions for customers and partners.
“The UK travel market is fiercely competitive but I believe that a comprehensive price comparison model offers real value to consumers who want the best prices from the leading travel providers".
As part of his new duties, Singer will work alongside recently-appointed chairman of Icelolly Tony Wheble, - formerly chief executive of James Villa Holidays and chairman of Original Travel.
Andy Lees, non-executive director of Icelolly and partner at the company’s majority shareholder Palatine Private Equity, said: “The board’s thanks go to Andrew Latham for his role in developing the Icelolly.com brand into one of the most-recognised in the UK holiday market.
"Richard’s experience in media, internet marketplaces and customer marketing will help build on the achievements of the Icelolly team and we look forward to growing the business over the next few years.”