The son of longtime NHL defenseman Craig Wolanin went directly from the University of North Dakota to the Ottawa Senators in 2017-18, playing in 10 NHL games and finishing with three points (one goal, two assists). He made his NHL debut on March 22, 2018, in a 6-2 loss to the Edmonton Oilers, and scored his first goal 11 days later in a 6-5 loss to the Winnipeg Jets.
In 2018-19 Wolanin played in 30 games for the Senators with four goals and eight assists. He also played in 40 games for Belleville in the American Hockey League and made the 2019 AHL All-Star Game. He also played in six games for the United States at the 2019 World Hockey Championship in Slovakia.