Women & Business Profile: Lee Ann W. Caliendo

“... Listen first. So many times, we want to dive right in but do not know the details. Listen first to formulate a great plan for a better chance of success.”

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Lee Ann W. Caliendo
Account Executive
UPMC Health Plan

Lee Ann W. Caliendo’s career has traversed several titles and industries.

She began as a headhunter for IQ Inc., a woman-led IT company based in Murrysville before working for UPMC Health Plan as a recruiter in human resources. Eight years after joining the company, she shifted to account management.

“There was a large learning curve, and I needed to obtain my insurance license, but it was invigorating,” Caliendo says.

In 2014, Caliendo began her current position as an Account Executive for UPMC Health Plan. Her role includes working with non-profit and for-profit clients to strategically implement insurance plans, wellness programs, pharmacy programs, and other ancillary products that provide coverage for employees and affordability for the organization.

Throughout her career, Caliendo has received numerous awards for programs she developed and led, including Goodwill’s Power of Work Award for UPMC’s Pathways to Work feeder program, which trained and developed people receiving Temporary Assistance for Needy Families into full-time employees with career options. She also received the You Are A Star Award from UPMC Human Resources department for leading a Nursing Care Manager Job Fair and Workshop which resulted in hiring 19 uniquely qualified clinical professionals.

When COVID-19 emerged, Caliendo, a caring problem solver who likes to get things done, began focusing on how to keep clients’ employees safe and informed during the pandemic.

“Being in the health insurance industry during the pandemic gave me a front row seat to the ever-changing landscape of COVID-19,” she says. “Providing updated information to my clients so they could help their employees navigate vaccines, testing and treatments is my top priority.”

In addition to her work at UPMC, Caliendo contributes to the community through her commitment to being a life-long blood donor. A parent of a child with Down Syndrome, she has volunteered with Special Olympics of Allegheny County for 30 years and served as their treasurer and historian.

“The athletes inspire me through their oath, ‘If I cannot win, let me be brave in the attempt,’” Caliendo says.

What’s Caliendo’s advice to other women in business? “Follow through. Make sure you fulfill your commitments,” she says.

The best advice she has ever received is to “Listen first.”

“So many times, we want to dive right in but do not know the details. Listen first to formulate a great plan for a better chance of success,” Caliendo says.

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