He is a longtime resident of Provincetown, Massachusetts US and the shifting dunes, landscape, the sea and the community are his palette. He has utilized sand, Christmas trees, fish skins, language, plastic tampon applicators washed up on beaches, condoms and pre-demolition buildings and selected sites and materials in his work. 

He gave a TEDx Talk: Portrait of the artist as a corporation.

He has taught at the Museum School of the Boston Museum of Fine Arts (Tufts), and has had residencies at: Harvard University (where he lectured); AS220 in Providence, RI; Williams College in Williamstown, MA; Real Art Ways in Hartford, CT; Harvestworks Digital Media Arts Center, NYC; Milepost 5 in Portland, OR; Fundacion Valparaiso, Mojacar, Andalucia, Spain; CAMAC, Marnay-sur-Seine, France; and the Santa Fe Art Institute, NM and Cill Rialaig Arts Center.

His movie, Toilet Treatments, won an HBO Award and his 2015 survey show at Provincetown Art Association & Museum travelled to Florida Atlantic University in Boca Raton. He won a controversial Trademark from the US for his Old Glory Condom Corporation patriotic condoms. He has received awards from the Boston Society of Architects for his visionary, environmental proposal, Martucket Eyeland Resort & Theme Park, and the Cooper Hewitt, Smithsonian Design Museum in NYC for his Big Dig project, The Big Twig. He recently gave the keynote speech at the UK Conference on Menstruation and Sustainability in St. Andrews, Scotland where he performed a ceremony on the North Sea as Miss Tampon Liberty. He was long listed for a sculpture competition for the O'Connell Plinth in front of Dublin City Hall, The Great Wonder. 

Jay was honored in 2012 by the Massachusetts State Legislature as an artist and founder and director of the Provincetown Community Compact, producer of the Swim for Life, which has raised $8M for AIDS, women’s health and the community (the 39th Swim is Saturday, September 12, 2026).