Kepcher began her foray into business by selling Avon Products door-to-door. Following high school she took a job as a waitress at a Manhattan restaurant, and ultimately attained the role of manager. She learned teamwork attending Mercy College in nearby Dobbs Ferry on a volleyball scholarship. She graduated with a marketing degree. Despite having little experience, in 1992 Kepcher secured a position as sales and marketing director of a golf club outside New York City. Her primary responsibility was to prepare the property for bank auction, where it was eventually sold to Trump. Kepcher's ideas on how best to use the property impressed him, and he hired her as director of sales and marketing in 1994.

After four years in this capacity, she was named interim general manager after then general manager Karl Hofer was ousted from the organization. Her effective management skills convinced Trump of her ability to lead and he later named her the Chief Operating Officer and General Manager of the Trump National Golf Club in Briarcliff Manor, New York, and subsequently the Trump National Golf Club in Bedminster, New Jersey, overseeing over 250 employees at each location.

In 2004, she wrote the book Carolyn 101: Business Lessons From the Apprentice's Straight Shooter (ISBN 0-7432-7022-3) based on her business experience.

On August 31, 2006, Kepcher's employment at the Trump Organization abruptly ended. According to sources who spoke to The New York Post, Trump felt that Kepcher's newfound celebrity status had kept her too busy with speaking engagements and endorsements to focus on her responsibilities for the Trump organization. Kepcher was replaced on The Apprentice by Ivanka Trump, beginning with Season 6.

Following her departure from the Trump organization, Kepcher became co-founder and CEO of Carolyn & Co., a company created for the purpose of "providing a broad array of services and assistance to career women." The company's website is www.WorkHerWay.com

In November 28, 2006 Carolyn was hired by Microsoft to star in a new reality show, Ultimate Challenge, to find the next best small-business venture. She was to be one of the 3 judges. The contest winner would get $100,000 in seed money, a storefront or other business space in Manhattan rent-free for a year, and software to help get their business started. The pilot show was never completed.

In January 2007, Kepcher provided management skills to the nonprofit world through an affiliation with Graham-Pelton Consulting, Inc., a national leader in fundraising and nonprofit management. Since 2007, she has been a career advice columnist with the New York Daily News.

Kepcher is of Irish descent. She has two children, son Connor (born in 2000) and daughter Cassidy (born in 2002), and lives in Ridgefield, Connecticut. Kepcher holds an honorary degree from Bryant University.