She's also noted for her recurring roles on several television series, including the voices of Renee the Receptionist and Joy Peters on the Adult Swim comedy Tom Goes to the Mayor (2004–2006); Marge on the AMC drama Mad Men (2007); and Diane on the ABC comedy Cavemen (2007).

She also appeared in the season 2 premiere of Men of a Certain Age. Courtney is a member of The Groundlings, an improvisational and sketch comedy theater in Los Angeles, California.

Courtney was born in Stony Point, New York, the youngest of three children of a high-school history-teacher father and a singer mother.

In 1992 she graduated from Binghamton University, where she had played Elizabeth Proctor in The Crucible. By then, she said, “I was never tortured over whether I wanted to become an actor. There was never another option in my mind.”

After graduation, she moved to New York City, where her roommate was future author and columnist Megan Daum.

While working as evening secretary for Smith Barney chairman Robert S. Greenhill, Courtney studied acting at the Neighborhood Playhouse.

She moved to Los Angeles, where she roomed with her sister, actress Jennifer Courtney. The two wrote and performed the sketch "Those Courtney Girls" in Los Angeles and at the Aspen Comedy Festival.

She joined the training program of the improvisational and sketch comedy group The Groundlings, and in 2004 became a member of its 30-person main company.

There she met its theater's lighting director, Scott Kolanach,whom she married in 2008.

During her early time in Los Angeles she worked odd jobs to support herself, including catering.

Courtney broke into television commercials with a Bud Light beer ad on a Super Bowl. She went on to appear in commercials for Skittles, SC Johnson Glade products, General Mills, and Weinerschnitzel.

She began her role as Flo, a quirky, chipper sales clerk in an abstract insurance retail store in a series of Progressive Auto Insurance commercials in 2008

The campaign's designer, Progressive executive Chris Owens, said in 2010, "We wanted to show how easy it was to buy insurance and how Progressive was a great value. We decided to put a fun and energetic face on it, someone who had a great personality and was friendly with customers. Stephanie came to the audition and gave such an amazing performance, everyone looked at each other and said, 'She's our girl.'"

The actress considers the character "me at my silliest. You start off with a script, but at the end they usually let me put a little zinger in there. ... Flo could be one of my improv characters, always on and sort of cracked in a weird way."

To create the look, "They tease my hair, spray it and stick the headband in it. And the makeup is like painting a portrait on my face. ... It totally changes things on my face. It's like having a mask on."

The character's sex appeal to some viewers baffles her, she said: "I don't know what it is.

The way I play her, she's pretty much the most asexual thing on TV right now. I think the Geico lizard puts out more sexual vibes than Flo does."

She has appeared in such films as The Brothers Solomon, Blades of Glory, The Heartbreak Kid, Melvin Goes to Dinner, for which she and the ensemble cast were awarded the Copper Wing at the 2003 Phoenix Film Festival, and Fred: The Movie.

Courtney was a member of the improv team Sliced Bread, which appeared on the improv-comedy competition World Cup Comedy on the Ion Network, then the Pax Network.

She appeared on the season-three episode "Dad" of Angel, as well as on a season-seven episode of House M.D., entitled "Selfish", the Everybody Loves Raymond episode "Cookies" and the United States of Tara episode "Aftermath

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