Jaitley ta fara aikinta ne daga aikin tallace-tallace a kamfanin wayar hannu a Kolkata kafin ta yanke shawarar shiga gasar kyawawan kyawawan wurare. Ta lashe lambar yabo a Femina Miss India 2001. Ta kuma lashe kyautar Miss Margo Beautiful Skin, Indiatimes Surfer's Choice, da MTV's Most Wanted. Daga baya an tura ta zuwa gasar Miss Universe 2001 da ke wakiltar Indiya inda ta gama ta 4th runner-up. A shekara ta 2001, ta fito a cikin bidiyon kiɗan Jazzy B na "Oh Kehri", wanda ya shahara sosai. Ta kuma fito a cikin bidiyon kiɗa na Bombay Vikings. A shekara ta 2003, ta fara fim dinta a fim din Feroz Khan Janasheen. Fim ɗin ya sami nasara a ofishin akwatin a Indiya. A karo na biyu da aka sake ta, ta yi rawar da ta dace da Sunny Deol a cikin wasan kwaikwayo na soyayya na Femina Miss India, amma ta sami kyautar Miss Margo Beautiful Skin, Indiatimes Surfer's Choice, da MTV's Most Wanted.
Miss Margo Kyakkyawan Fata, Zaɓin Indiatimes Surfer, da kuma MTV Mafi So