Sherwood earned stability in the Bay Area when he signed a five-year, $28.75 million contract (average annual value of $5.75 million) with the Sharks on March 4, 2026. The undrafted forward was acquired by San Jose in a trade with the Vancouver Canucks on Jan. 19, 2026, with his 17 goals leading the Canucks at the time of the deal. He played the previous 309 NHL games for the Anaheim Ducks, Colorado Avalanche, Nashville Predators and Canucks.

Prior to his professional career, Sherwood played three seasons at Miami University (Ohio) and two for Youngstown in the United States Hockey League (USHL). He signed a two-year, entry-level contract with the Ducks as a free agent March 20, 2018, played in the American Hockey League for San Diego, Colorado and Milwaukee, and was named to the league's second All-Star team after the 2021-22 season with 75 points (36 goals, 39 assists) in 57 games for Colorado. He played for the Avalanche and Predators before establishing himself as an NHL regular with the Canucks.

Sherwood signed a two-year, $3 million contract (average annual value of $1.5 million) with Vancouver on July 1, 2024. He scored his second NHL hat trick in the Canucks' 4-3 shootout win at the St. Louis Blues on Oct. 30, 2025, his first coming with Vancouver in a 3-1 win against Colorado on Dec. 16, 2024.