Born in Santa Monica, California, Kiff began acting in the early 1980s. In 1982, she appeared in the NBC comedy Love, Sidney as Patti Morgan opposite Tony Randall and Swoosie Kurtz. In 1984, she landed the role of Kelly Cleaver, daughter of Wally (Tony Dow) and Mary Ellen Cleaver (Janice Kent) and later, older sister to Kevin Cleaver (Troy Davidson) in the 1985 revival series The New Leave It to Beaver. After the series ended in 1989, Kiff acted sporadically in mainly bit roles
In 2008, she produced the musical short E vuoto per amore (He Is Empty for Love), directed by Galen Fletcher, screened at the Red Rock Film Festival. In 2008 she directed a short film titled Alice & Huck, starring Allison Mack from the TV series Smallville. The short won three accolades at The Big Easy Shorts Festival: Best Director (for herself), Best Editing, and Best Drama. She co-created and directed the first five episodes of the online science-fiction/fantasy webseries Riese: Kingdom Falling which aired in 2009.
In 2014 Kiff produced the comedy thriller film The Legend of Barney Thomson (originally titled The Long Midnight of Barney Thomson.
