Rubuta ci gaba ga wannan sakin layi - Gregory ya shiga rundunar sojin sama a shekarar 1977. An sanya ta zuwa Wing na Flying Training na 47, 3rd Tactical Fighter Wing, da Pacific Air Forces kafin halartar Kwalejin Kwamandan Sojoji da Kwalejin Kasuwanci na Sojojin Sojoji. Daga baya ta yi aiki a matsayin Mataimakiyar Soja ga Sakataren Tsaro na Amurka a lokacin da aka rantsar da Shugaban kasa a shekarar 1993.
Ka yi haƙuri. Bayan kammala karatunta daga Kwalejin Masana'antu na Sojoji a shekarar 1994, an sanya ta aiki tare da Shugabannin Hafsoshin Hafsoshin kuma ta zama Shugaban Sashin Nazarin Kudi na Kasafin Kudin Sojojin Sama na Pacific a shekarar 1996. A cikin 1999, an nada ta Daraktan Gudanar da Harkokin Kasuwanci da kuma Mai Kula da Rundunar Sojojin Sama na Sojojin Sama kafin a sanya ta a Ofishin Mataimakin Sakataren Sojojin Sama don Gudanar da Harkokin Kasuwanci da Mai Kula. Ta yi ritaya daga ranar 1 ga Satumba, 2006.