In 1971, Osberg earned his first head coaching gig for Wayzata High School.
[4] In 1977, he left Wayzata to become the defensive coordinator for his alma mater, Augsburg, under head coach Al Kloppen.
In 1991, he returned to Augsburg as the head football coach as the successor to Bill Hunstock.
He coached the team to its only Minnesota Intercollegiate Athletic Conference (MIAC) title and a trip to the NCAA Division III playoffs.
[8] While Osberg was serving as a coach for Wayzata High School he also taught biology.