Cupid, owner of sites such as Maturedating.com and Girlsdateforfree.com, has seen revenues and profits soar since joining the stock market in 2010, but its share price has stalled as investors fretted about the sustainability of its business model.
Having announced a share buy-back last week, it has now revealed it has appointed Mr Stirling as chief financial officer and company secretary to beef up the top ranks of its management team.
Mr Stirling will join Cupid's board on January 3 next year.
He has been working with the seven-year-old company since August, leading its five-year planning process.
Mr Stirling was chief financial officer of Red Bull North America from 2006 to 2008 and then held the same role at the Performing Rights Society.
Current finance director Mark Doughty, will remain on Cupid's board as commercial director to focus on developing markets as the company targets international expansion.
Cupid has also recruited Phil Gripton, former chief operating officer of digital marketing business LBi/bigmouthmedia, as managing director of dating services.
Vladimir Levykin, current head of operations, will become managing director of social discovery to develop its Facebook, mobile and social dating products.
Tatyana Seredyuk, director of marketing, will become senior vice president for North America.
Cupid chief executive Bill Dobbie said: "We are very pleased to announce these appointments, which will significantly broaden the executive management team at Cupid .
"These and the other changes will support the company in the continued execution of its rapid growth trajectory."
Cupid's shares fell 1p or 0.6% to 178.5p.
This is almost three times its 60p listing price but down from the heights of 250p touched last year.