[5] Greenman was an established society painter in Minneapolis by the early 1920s and made portraits for Hollywood stars, politicians and socialites.

Her 1921 exhibition at the Bradstreet Gallery in Minneapolis was described in American Art News as "alternately gay and serious, prismatic and tonal.

"[6] Greenman was awarded first prize in painting at the seventh and eighth annual exhibitions of Twin City Artists.

[7] Greenman was replaced as a judge during the 1925 Iowa State Fair's Art Salon due to her modernist inclinations.

[8][9] Following the Wall Street crash of 1929, Greenman left New York and supported her family by painting portraits for wealthy clients.

Her 1922 work A Moment's Rest for Mrs. Hoscovics and her portraits of Polish immigrants in Wisconsin show that Greenman wanted to use her art to explore social issues.

[10] Greenman painted portraits of many famous people, including conductor Emil Oberhoffer, Dolores del Río, and Mary Pickford.