Kailey got her start in golf learning from her grandfather, a teaching professional. Attending Southern New Hampshire University on a golf scholarship, Kailey played four years for the Penmen, before earning a P.J. Boatwright Internship with the United States Golf Association and later working as an intern for the New Hampshire Golf Association. The last four years, she has spent her winters working at The Club at Mediterra in Naples, Florida and spent her summers at Cape Neddick Country Club in Cape Neddick, Maine. Kailey is a PGA Associate along with being a Certified Coach for U.S. Kids Golf and PGA Junior League. She is also a member of the Positive Coaching Alliance.