Payne signed terms as a first year apprentice prior to the start of the 2008/09 season and made an immediate impression at Gillingham.

Although a Midfielder, Jack appeared at right-back for the Reserves that season before making his senior debut for the club as a late substitute in the 2-0 home win over Chester City.

In January 2009 he put pen to paper on his first professional contract with the club and completed a dream year by winning the Gills Young Player of the Year Award.

Following an injury to Kevin Maher in pre-season Jack started the 2009/10 season in the Gills holding midfield role and earned a standing ovation for his performance in the 5-0 thrashing of Swindon.

His early season form was rewarded with a new three year contract midway through the campaign while the youngster earned rave reviews for his displays filling in for injured skipper Barry Fuller at right-back.

Jack ended the 2009/10 campaign by collecting the Gills Young Player of the Year Award for the second season running.