Kern attended the Tenth Van Cliburn International Piano Competition in 1997 and did not progress past the R1 level.

Kern attained international prominence when she became the first woman in over thirty years to receive the Nancy Lee and Perry R. Bass Gold Medal in the Eleventh Van Cliburn International Piano Competition in June 2001, which she won jointly with Stanislav Ioudenitch.

An additional documentary was made about Kern following the 2001 Van Cliburn competition, titled Olga's Journey (2003).

[6] Besides performing, Kern is an active music pedagogue, and has conducted master classes at such locations as Yale University, the Royal Conservatoire of Scotland, and New York City's 92nd Street Y.

[10] Kern was jury chairman for the Seventh Cliburn International Amateur Piano Competition in June 2016.

[15] The competition gave away a total of $30,000 in prize money with the winner receiving $11,000 along with a professional recording on the Steinway & Sons Label and tours throughout Europe and the United States.

The aim of the foundation is to provide financial and artistic assistance to developing young musicians throughout the world.