This award was established in 1990 and re-named for AFA’s first Executive Director, Gayle Webb, upon her retirement in 1999. The purpose is to annually recognize outstanding contributions to the field of fraternity/sorority advising by one AFA member who is a campus-based professional and one AFA member who is an inter/national organization staff member during the individual’s first three years of Association membership (not inclusive of time as a graduate student or inter/national organization consultant). Nominees will be judged on achievements in their professional experience and impact at either a college/university or as part of an inter/national organization staff, contributions to the field of fraternity and sorority advising broadly including Association service, and outstanding projects/program/initiatives implemented during their professional experience. Two awards may be given each year, one to a campus-based professional, and one to a headquarters professional.
| Year | Recipient |
| 2023 |
Lindsy Perry, Austin Peay State University |
| 2022 | Patrick Githens, Sigma Phi Epsilon Fraternity Jayde Ware, Iowa State University |
| 2021 | LaShatà Grayson, Indiana State University Will Cangialosi, The Ohio State University |
| 2020 | Lorae Bonamy, University of Maryland, College Park Christina Parle, Zeta Beta Tau Fraternity |
| 2019 | Jessica Ashton, East Carolina University Brooke Goodman, Delta Phi Epsilon |
| 2018 | Hunter Hartwig, The Ohio State University |
| 2017 | Brittany Barnes, Purdue University Kate Wehby, Alpha Sigma Tau Sorority |
| 2016 | Bonny Shade, University of North Carolina, Charlotte |
| 2015 | James Crawford, Vanderbilt University |
| 2014 | Leslie Schacht, University of Iowa |
| 2013 | Christina Wellhouser, University of California, Berkeley |
| 2012 | Alex Brown, Keene State College |
| 2011 | Annie Carlson, University of Oregon |
| 2010 | Michelle Marchand, Lehigh University |
| 2009 | Veronica Hunter, Lehigh University |
| 2008 | Lindsay Sell, University of Connecticut |
| 2007 | Amy Rosen, Otterbein College |
| 2006 | Shannon Greybar Milliken, DePaul University |
| 2005 | Megan Johnson, Dartmouth College |
| 2004 | Kyle F. Jordan, Washington State University |
| 2003 | Nicole Manley, Duke University |
| 2002 | Nathan Thomas, Bradley University |
| 2001 | Todd Sullivan, Florida International University |
| 2000 | Dan Bureau, University of New Mexico |
| 1999 | Jon Ness, Loyola University, New Orleans |
| 1998 | Mike McRee, University of Oregon |
| 1997 | Stephen Rupprecht, Pennsylvania State University |
| 1996 | Mary Beth Carroll, University of South Carolina |
| 1995 | Thomas Jelke, Florida State University |
| 1994 | Walter Kimbrough, Emory University |
| 1993 | Noel Landuyt, University of Texas, Austin |
| 1992 | Joseph Bertolino, East Stroudsburg University |
| 1991 | Mark Latimer, University of Oregon |
| 1990 | R. Brit Katz, Northeast Louisiana University |