Len was born and raised in New England before graduating from the United States Merchant Marine Academy in 1999 with a BS in Marine Transportation and a commission in the Naval Reserves. While sailing as a third mate on various cargo ships, Len earned his MBA from the University of New Hampshire in 2004 with a specialization in finance. Len came ashore working for Hess Corporation in New York from 2004-2007 and for the ship brokerage firm Charles R. Weber Company in Greenwich, Connecticut from 2007-2014 before taking on the role as Marine Terminal Director for the Port of Olympia from 2015-2021. Len joined Jones Stevedoring January 2022 in a sales position.