Trautmann was one of the founders of the Industrial Workers of the World. He helped write the Industrial Union Manifesto, one of the IWW's founding documents. While in the Industrial Workers of the World Trautmann worked as an organizer, propagandist, and for some time as secretary-treasurer. He was much more known for his essays than for his administrative skills. His works include One Big Union, Why Strikes are Lost & How to Win, and Industrial Unionism: The Hope of the Workers. He was thrust into a leadership role with the resignation of Eugene Debs from the union, and while he was a skilled writer his administrative skills were lacking. He could not keep a record of the members of the union (that is both the individuals and the different local branches of the IWW), and at the 1906 IWW convention, it was discovered that Trautmann had not been keeping a financial record for the entire year.