BetterUp's Jolen Anderson on rejecting the flawless executive persona and leading with empathy, clarity and humanity.
Emma Coppin
Multimedia Content Lead, Thought Leadership and Customer Stories
Workday
For Jolen Anderson, chief people & community officer at BetterUp, leadership has never been defined by clean spreadsheets or sterile corporate theories. Instead, her career has been a dynamic blueprint in balancing enterprise demands with the unpredictable, beautifully chaotic reality of human life. "I found myself with three children under the age of three – including a newborn set of twins – at the exact moment I took on one of the most demanding executive roles of my career," she said.
By embracing the reality that life and business are always in motion, she has built a career that bridges high-level corporate strategy with the real stories of the people she leads, meeting change not with the pretence of certainty, but with the adaptability to move through it.
"I found myself with three children under the age of three – including a newborn set of twins – at the exact moment I took on one of the most demanding executive roles of my career."
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Jolen's approach to leadership was shaped by her upbringing as the daughter of immigrant parents in a military family. Her father arrived in the United States from Panama as a teenager, eventually enlisting in the U.S. Army. During his first deployment in Panama, he met her mother, and the young parents began a life defined by frequent transitions.
Moving constantly meant navigating military base housing, adjusting to new schools and always being "the new kid". Jolen turned this childhood experience into a leadership superpower.
"I combine determination with a real sense of adaptability and empathy for what it was like to sometimes feel lonely, feel new, feel like you can't find your way," Jolen reflects. "I'd have to come into environments and observe, understand the ecosystem, and then react and adapt."
Her childhood instilled a fierce determination in her to tackle complicated problems while also balancing empathy for anyone trying to find their footing. It also gave her a lifelong appreciation for structured execution. "Understand the mission, understand the focus, get the job done," she says, nodding to the influence of her family's military discipline.
"Understand the mission, understand the focus, get the job done."
That analytical edge took Jolen to Northwestern University for her undergraduate degree in Social Policy and then for law school. She began her career in Chicago as an antitrust and labour litigator. While she initially entered private practice to manage law school debt, representing clients in high-stakes disputes highlighted a deeper calling. She realised her true interest lay in the human dynamics of law.
That insight drove her to transition from the courtroom to corporate strategy. She built an impressive executive track record, serving as the chief diversity officer and CHRO for the client organisation at Visa, and later as the global head of human resources for BNY, where she managed workforce strategies for 50,000 employees across 35 countries. Today, at BetterUp, she sits at the intersection of human transformation and organisational scale.
Despite her professional presence, Jolen admits she is a reluctant star. "I'm actually a much more behind-the-scenes person," she confesses, laughing about the oddity of a camera crew following her for a documentary. "I definitely don't seek the spotlight. I do it because it's a part of the job...you have to help tell the story of what your people are doing."
When her home life was upended in her mid-30s with three infants, Jolen hit a wall that completely transformed her leadership style. Until that point, her career had relied on pure individual effort, intense drive and a refusal to delegate. But the sheer volume of managing three young children forced her to rewrite her own playbook.
"My individual effort to sort of drive and enable my team was no longer enough. I was forced to delegate. I was forced to rely on others. I was forced to make sure I hired people who were better than me so that they could be their best. And that really was an unlock for me in my career."
During this intense part of life, advice from her mother – who had worked continuously while raising her own family – offered a helpful guiding principle: focus on being present for the specific moments that matter most. Her mother reminded her that young children have simple needs and will not remember every minor absence. Jolen applied that prioritisation to her corporate world, learning to focus entirely on high-impact work while intentionally letting go of the rest.
Today, Jolen operates in the flow of life, rejecting the rigid separation between "work" and "home". Managing her executive routine alongside her husband, she takes advantage of the natural rhythms of the day to anchor her mornings in family life before meetings begin.
Family group chats are the norm. No matter how old they get, Jolen, her parents and her sisters have a non-negotiable rule: always text the chat when your plane lands. On the road, she routinely switches hats from keynote speaker to mom – checking in via video call from an office couch in San Francisco to hear about her twins' school testing, celebrating their self-packed lunches or coordinating middle school pick-up logistics for her son.
On the weekends, she steps into her self-described "suburban mom starter pack" – acting as the family chauffeur for dance practices and baseball games. Furthermore, her service on the board of trustees for the Alvin Ailey American Dance Theater connects her professional focus on inclusion with her daughters' love of ballet.
"I was forced to make sure I hired people who were better than me so that they could be their best. And that really was an unlock for me in my career."
In a world currently disrupted by rapid technological shifts like generative AI, Jolen sees her role as helping people navigate change with a mindset of hope rather than fear.
"We are all just people trying to figure it out, trying to live our lives, trying to be our best," she says. For Jolen, technology should never replace human connection. Instead, clean data and automated tools should free leaders up to do what they value most: mentor, guide and develop their teams.
Guided by the leadership philosophy that "clarity is kindness", Jolen Anderson champions absolute transparency and shares clear expectations. Whether she is keynoting on a global stage or sitting on the sidelines of a local baseball field, she models a style of leadership that proves you can scale a business and develop its people without ever losing your connection to your family, your roots or your humanity.
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