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Heelan initially thought she was going to be in musical theatre. She first met her Ground Floor co-star, Skylar Astin, at a musical theatre convention.

Heelan's break-out TV role was on Cougar Town. She is credited as being a recurring character on Undateable and appears in three episodes plus the pilot. She was able to shoot both Bill Lawrence-helmed Ground Floor and Undateable simultaneously, as both comedies are multi-camera, which require fewer production days than single-camera days.

On Heelan's role in Ground Floor, TV critic Alan Sepinwall said Heelan is "simply terrific as Jenny: warm and quirky while always feeling like a strong and independent character". The Los Angeles Times said Heelan "makes Ground Floor watchable", describing her as "remarkably alive and in the moment; she makes real all that she touches. I could easily recommend tuning in just to watch her work – and hereby do."