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This may be mostly an issue of terminology. Treat the upfront payment as a fee for the service and then there's a contest with prizes. It's not gambling for the same reason it's not gambling when you pay an entry fee for a race with cash prizes.
Laws and regulations do not care what terminology you use, and many countries have extensive regulations on gambling and gambling web sites. If a technicality caused your site to be misclassified as gambling, then that would be the end of your site. And if you don't have a limited liability corporate shield around the site, it would also be the end of your personal finances. Unless you're really certain that you know what you're doing, you should consult a lawyer before proceeding.
The magic word here is "escrow". This is an escrow service, not betting or a bank. Alternatively, it might be considered a bonding service. Either way, though, it definitely needs competent legal advice and appropriate licensing for the jurisdictions you operate it in.