While at the NAHA, an elite level U-19 program for girls, he provided on and off the ice instruction, and also served as a college counselor, web site developer and manager, and director of residential life. Guiffre spent three years at the Tilton School in Tilton, New Hampshire, as a secondary boarding school teacher and coach. He taught photography, computer graphics, painting, and printmaking, in addition to many other courses. During his time at Tilton, Guiffre coached the Girls' varsity hockey team, and also coached the Girl's Varsity Soccer team to a NEPSAC championship appearance in 1999. He served as an assistant coach for the boy's varsity soccer team in 1997, when the team reached the NEPSAC quarterfinals.
His soccer coaching extended to his work at the Windridge Camp at Teela-Wooket in Roxbury, Vermont in 2000. Here he served as the Director of Soccer, where he designed and implemented a soccer program for a specialty sports camp for up to 200 students per session. Guiffre is the Founder and Presenter of Proactive Solutions, an independent consulting service, offering customized seminars, workshops and retreats focusing on communication and cooperation skills. Recent clients of Proactive Solutions include Renaissance Worldwide Corporate Law Department, and Windridge Camp Staff.
A 1996 graduate of the University of Vermont, Guiffre earned a B.A. in political science and a minor in Studio Art. He is currently finishing a Masters of Sport Science at The United States Sports Academy.