- United States Navy, 1969-1971: surface line officer, USS Glover AGDE-1[6]
- Yale Law School, J.D. 1974[6]
- Employed by Hill & Barlow, 1974-1978: associate attorney, tax and corporate departments, specializing in employee benefits[6]
- Boston University School of Law: associate professor of law 1978–1980[6]
- Cornell University: associate professor of law, 1980–1982; professor of law, 1982–1988; editor, Law and History Review, 1982–1987; dean and professor of law, 1988 to July 1998[6][10]
- Grinell College: twelfth president of Grinell College, 1998-2010; professor of history and science
Osgood's administrative actions at Grinnell revolved around a strategic plan approved by the trustees in Spring 2005. The five-year plan's goals included increasing the emphasis on inquiry-based learning and broadening the curriculum; fostering faculty, student, and staff sense of ambition, adventure, and well-being; advancing Grinnell College as a more diverse, robust intellectual community; improving the fiscal balance and stability of the college; contributing to the vitality of the city of Grinnell; and strengthening the public profile of Grinnell College, Grinnellians, and the value of a Grinnell education.[11]
The Grinnell campus underwent much construction and renovation in the 2000s. Though the plans began during the tenure of the previous president, Pamela Ferguson, many of the projects occurred under Osgood. World-renowned architect Cesar Pelli designed several of the recent buildings.
Osgood stepped down from his post as president of Grinnell, effective July 31, 2010.[12] The Board of Trustees later chose Raynard S. Kington as Osgood's successor.[13] Reflecting on his experiences teaching both undergraduates and law students, Osgood said he "enjoyed interacting with law students as a teacher and dean, but he says he enjoys undergraduates more. 'I like law students,' he says, 'but they're much more developed and formed. Undergraduates are still making fundamental choices in their life. It’s more interesting to interact with them.'"[14]
In January 2011, Osgood was named a semi-finalist for the position of Dean of the Boston College Law School.[15]
Osgood is married, with four grown children[6] and three dogs.[16]
Osgood is a runner, and students and faculty have reported seeing him jogging at very early hours in short, red swimsuits.[17] "I have about 15 pairs of bathing suits," Osgood said, "About half of them are red. I don’t know why I have 15. If you see me around my house at night, you’ll see me wearing them. I just wear them as shorts. Not just for running purposes—I wear them when I fly on planes.”[18]
Cases and Materials on Employee Benefits. with Peter J. Wiedenbeck, Washington University in St. Louis
The Law in Massachusetts. The Supreme Judicial Court 1692-1992, Editor and Contributor, 1992, Supreme Judicial Court Historical Society
The Law of Pensions and Profit-Sharing. Qualified Retirement Plans and Other Deferred Compensation Arrangements (1984, Little Brown) with Supplements.
Bolten, Kathy A (February 20, 2006). "The Rising Price of a President". The Des Moines Register.
"History". www.lawschool.cornell.edu. Archived from the original on 19 December 2008. Retrieved 30 May 2009.