Praised by critics for her "deep, soulful sound" and "powerful, enchanting renditions," Olga Dubossarskaya Kaler has toured three continents as a soloist, chamber, and orchestral musician. Her awards include the Special Prize at the Rodolfo Lipizer International Competition, and First Prizes at the Northwestern Concerto Competition and the Thaviu-Isaak Competition. Kaler’s orchestral engagements include the World Orchestra For Peace directed by Valery Gergiev, the Chicago Symphony, Boston Symphony, Indianapolis Symphony Orchestra, as well as leadership positions with the Rochester Philharmonic, Syracuse Symphony, Lake Forest Symphony, and Ars Viva! Orchestra. Kaler is currently a member of the Chautauqua Symphony Orchestra of New York under the direction of Rossen Milanov. She is also a long-time member of The Chicago Ensemble, with whom she performs frequently.

Kaler has appeared as a soloist, chamber musician, and artist-teacher at the InterHarmony International Music Festival in Italy, the Bowdoin International Music Festival in Maine, as well at festivals in Skaneateles, NY,  in Montreal, Canada, in Steamboat Springs, Colorado, in Athens, Greece, and the Villa Musica and Schleswig-Holstein Festivals in Germany. Kaler has appeared in concert on some of the world’s most legendary stages, including the Carnegie Hall of New York, the Great Hall of Moscow Conservatory, the Albert Hall of London, and the Berlin Philharmonie Hall, to name a few. She is highly sought after as a national and international competition judge and chamber music partner, frequently sharing the stage with many of today's leading artists.