Jenny Dearborn SAP
Former Chief Talent Officer
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When Jenny Dearborn gets stuck, she often thinks back to her “forever mentor,” Karie Willyerd, and considers “what would Karie do?”
“That’s what a mentor does,” Dearborn said. “They remain a voice in your head, a little something on your shoulder, to sort of give you advice. Karie would step back, be unemotional and objective, look at the facts, take a scientific approach, create a hypothesis, do a little bit of research, gather some data and come back with a balanced recommendation or next steps.”
After a career spanning multiple chief learning officer (CLO) roles in the technology industry, Dearborn is a full-time board director, advisor and investor. Willyerd was one of her earliest managers. The two met at the former Sun Microsystems, where Dearborn spent six years and served as CLO for sales and services in the Americas.
“Corporate learning just felt really noble…like a higher calling to help people in the workplace be more successful and fulfilled,” Dearborn said. “Learning, in my psyche, is the greatest thing a person can do. You are on your way to be your highest and best self. I love being a part of that epiphany process.”
Dearborn believes that passion stems from her childhood struggles with learning. She barely graduated high school and wasn’t diagnosed with severe dyslexia, attention-deficit/hyperactivity disorder and obsessive-compulsive disorder until she was 18.
“In all my first jobs, it just took me longer to process things,” she said. “If somebody else was reading documents, I would just take four times as long. It makes sense, in retrospect, that I was successful as an instructor up in front of a room performing and absorbing content auditorily instead of in written form, because my Achilles heel is reading.”
Professionally, Dearborn was not open about her neurodivergence until well into her career, when she became chief talent officer at software company SAP. “It was something I still felt a great amount of shame and embarrassment about, and I actively hid it at work for most of my career,” she said.
SAP had set a corporate neurodiversity goal of having at least 1% of its workforce represented by individuals on the autism spectrum by the end of 2020. “The corporation saw value in that, and I was so blown away and taken aback by how amazing that was,” Dearborn said. She very cautiously began mentioning her neurodivergence to colleagues and, she noted, “the earth didn’t stop spinning on its axis.”
Teaching – specifically high school English – had been Dearborn’s objective from the start of college. She earned a bachelor’s degree in English at the University of California, Berkeley, and a master’s in education at Stanford University before teaching English, public speaking, drama and creative writing at a San Francisco Bay Area high school for two years.
In hindsight, it was a great first job, according to Dearborn. “Looking back, I learned a lot and have great fondness for the experience,” she said. “In the moment, though, I was pretty overwhelmed and didn’t really feel super prepared. I went to school each day not really feeling confident that I was very good.”
But Dearborn later became friendly with some of her former students, and they said otherwise. “They say I was a great teacher, but I don’t remember it that way,” she said.
That uneasiness, coupled with not knowing what to do next, prompted Dearborn to pursue 46 informational interviews at Hewlett-Packard (HP) in her second year of teaching. And just a few days after the high school’s graduation, she pivoted to corporate instruction there. As part of the human resources department’s training and learning team, Dearborn taught courses including “Welcome to HP” for onboarding, “Seven Habits of Highly Effective People,” and business process automation and management leadership.
The tech world was a logical career path for the Silicon Valley resident, who subsequently joined Docent Software (now SumTotal Systems) as CLO. While she was responsible for internal employee learning, Dearborn quickly recognized that Docent customers and partners also needed help installing and configuring its software and selling and supporting it. Her success in tackling that brought in a new revenue line and led her from human resources to the company’s sales team.
“Everything that I was developing had a commercial value,” she said. “That sort of started my journey into carrying a quota and being part of sales.”
Dearborn credits her breadth of roles for her faster path to a CLO seat. “I knew all of the pieces and how they came together,” she said. “I was a learning architect. I sold learning. I was an instructor. I was a learning designer. I have a deep understanding and knowledge of learning technology and all the different up-and-coming players.”
Dearborn’s transition to present-day board director, advisor and investor, meanwhile, benefits from an MBA from San Jose State University and her mentoring of companies in SAP’s startup ecosystem.
“They really helped me see that I brought a lot of value,” said Dearborn, who began taking on small human resource, education and work tech clients after leaving the company. “I’ve been a seller at the highest level, and I’ve also been a buyer at the highest level. I am uniquely well-positioned to help these companies.”
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