Born in Atlanta, Escarra grew up around Decatur, Ga. Her father worked for General Motors while her mother was hospitalized for extended periods with severe depression.
"If you think back to the '50s and emotional issues," Escarra said, "they really weren't understood at all."
At times, Escarra and her younger brother went to live with her grandmother in Athens, Ga. Before her grandmother intervened, Escarra said, her father struggled to pay her mother's medical expenses.
"We would go for days with just eating at school and not eating at home. Just lunch," Escarra said. "So it was pretty grim."
These formative experiences, she said, give her empathy for the people she serves.
Maura Daly, chief communication and development officer at Feeding America, recalled a trip with Escarra to New York, where they helped at a soup kitchen. Escarra carried a pot of coffee to serve clients, some of whom had walked two hours to get a meal.
"This guy asked her where she lives, and she said Chicago," Daly said. "And the guy immediately started telling her a story where he was envisioning himself being an actor on the Millennium Park stage. ... Vicki put down her pot of coffee and sat on the floor by his chair and listened to him for 15 minutes. That's when I realized that she really is that CEO to whom it doesn't matter who's in the room. She treats every person she meets in life with that same level of dignity."
In February, Michele Sullivan, president of the Caterpillar Foundation, spent four days traveling with Escarra in Uganda, meeting with local loan officers and clients.
They had driven three hours outside of Kampala, the capital, to visit a school funded in part by a loan from Opportunity. Children surrounded Escarra, Sullivan said, and she told them, "'You can do whatever you want.' She looked right at them, and with all seriousness said, 'I'm sitting in front of the future president of Uganda. I'm not kidding you. I'm telling the truth.'"
For Escarra, the way forward came through work and education. At Georgia State University, she majored in business and psychology while working in retail, modeling, and answering phones and doing clerical work for Delta Air Lines.
After graduating in 1976, Escarra was interested in joining the Peace Corps but decided to defer those plans for a year to be a flight attendant.
A few weeks before finishing that year, she met Delta's then-CEO Dave Garrett on a charter flight.
When Garrett began chatting with the crew, she told him she was "going to go and do something really meaningful with my life."
"So he laughed, and said, 'Well, why don't you come by my office because I have a few jobs that might be of interest to you,'" Escarra said.
So began Escarra's ascendancy at Delta, first in human resources, then with a promotion every few years. She became director of in-flight service operations and later vice president of reservation sales. In 1996, then-CEO Ron Allen told Escarra that he would like her to oversee Delta's more than 200 airport operations around the world.
"I was like, I don't know how to run airports," she said. "But it was like, 'We're looking for leadership.'"
The move did not come without resistance from some colleagues. In addition to customer service and ticketing, Escarra led ground operations like baggage handling, fueling, catering and tower operations. The workforce she oversaw, she said, consisted of about 22,000 employees, a small percentage of whom were women.
Escarra recalls visiting Cincinnati for a meet-and-greet with about 100 ramp agents.
She said the head of Delta's operations at the airport introduced her to the crowd by saying: "I just want you to know that, as far as I'm concerned, you couldn't hold (the former supervisor's) jock strap."