For two decades, Wendy York helped internet and tech startups find their footing and grow. She founded a database marketing company and sold it to a national advertising agency. Eventually, she moved into venture capital, managing a private portfolio valued at $100 million.
She says that across her many jobs she has had “six distinct careers” but her skill set remains consistent. “What I usually bring to the situation is the ability to see a way to get to where they want to go, or to create a new process and to build the teams around it,” Ms. York says. “I’m very much a general manager.”
In 2008, she found herself without a job after the tech company where she was working downsized. Exit package in hand and in her early 50s, Ms. York paused to take stock. She had always balanced work and parenthood: While pregnant with triplets and on bed rest, she managed the sale of a company over the phone. But now her older daughter was in high school and her triplets were in third grade. “I realized that time was going to fly by,” she says.
She volunteered at her younger daughters’ school, treating the responsibility like a part-time job, until they were in fifth grade. The experience transformed her professional outlook.
“It was the first time in my adult life I had seen how much of an impact I could make that was measured in non-monetary means,” Ms. York says.
She began exploring a shift to nonprofit management, but earning money was still essential. As her savings dwindled and she interviewed for jobs, she repeatedly heard that she was overqualified. She applied for unemployment benefits for the first time.
In 2012, she spotted an opening for a managing director to oversee executive education at Stanford