During her keynote presentation at WIT’s 2026 Accelerate! Conference & Expo last week in Dallas, Simpson shared candid stories, professional challenges and leadership lessons from more than three decades at J.B. Hunt Transport Services.
Her central message? Becoming a “future-ready leader” requires courage, adaptability, confidence, meaningful relationships and the willingness to embrace opportunities — even when the path forward is uncertain.
When Simpson joined J.B. Hunt in 1994 after graduating from the University of Arkansas, she earned just $7.25 an hour and viewed the position as temporary. However, her father encouraged her to think bigger. Rather than pursuing another opportunity, he challenged her to envision becoming President and CEO someday.
That advice ultimately changed her trajectory.
Simpson described several early career disappointments, including a management promotion that went to someone else and a sales position that was unexpectedly placed on hold. Those setbacks eventually led her into a pricing role, where she gained exposure to senior leadership and opportunities that transformed her career.
Her lesson: Career disappointments can become unexpected opportunities for growth.
"In leadership, it's not about charting your path. It's about being adaptable when things don't necessarily go your way," says Simpson.
Simpson emphasized that professional growth requires accepting responsibilities before feeling completely prepared.
When J.B. Hunt challenged her to develop a new brokerage business, she faced considerable skepticism from employees, customers, carriers and investors. Rather than retreating, she helped build the business from the ground up, even sitting alongside employees making cold calls to demonstrate how to overcome objections and build customer relationships. The business ultimately reached $1 billion in revenue in 2017.
"There's not a single position that you will take that you are perfectly prepared for," Simpson told attendees.
Her advice for overcoming self-doubt and imposter syndrome was straightforward: Confidence comes from experience, and experience requires taking that next step.
Throughout her career, Simpson also helped turn around struggling business units and championed digital transformation, demonstrating how courageous leadership can create opportunities even during difficult economic conditions.
Looking toward trucking's future, Simpson discussed emerging technologies, artificial intelligence, autonomous vehicles and changing customer expectations.
She challenged leaders to anticipate disruption rather than simply react to it.
For example, she has asked J.B. Hunt executives to evaluate what the company's business model might look like if autonomous transportation became the starting point for strategic planning.
This certainly doesn't mean J.B. Hunt intends to become an “autonomous first” company. Rather, the exercise encourages leaders to challenge assumptions and prepare for possibilities. Simpson emphasizes that technology cannot replace the fundamental importance of human relationships.
"AI's going to change how we think," she observes. But relationships and trust remain essential.
She described J.B. Hunt's commitment to a "say-do" culture, which consistently delivers on promises and builds credibility through actions.
Her keynote message was clear: Future-ready organizations must embrace innovation while preserving the relationships and values that make them successful.
One of Simpson's most personal messages concerned balancing professional ambitions with family responsibilities and personal well-being.
After becoming a mother in 2001, she considered leaving J.B. Hunt because she struggled to reconcile her career with her family priorities.
Instead, a supportive leader encouraged her to explore flexibility. After welcoming twin daughters two years later, she worked part-time for two years. That experience reinforced an important lesson: Taking care of yourself enables you to better serve others.
Simpson also described how her father's cancer diagnosis prompted her to develop a personal mission statement centered on serving others and integrating faith, family, work and community.
She encouraged attendees to identify their own priorities and recognize that success looks different during different seasons of life.
During an engaging audience Q&A, Simpson addressed leadership vulnerability, managing increasing responsibilities and helping employees overcome self-doubt.
She encouraged leaders to recognize that emotional authenticity can be a strength rather than a weakness.
She also emphasized that advancing into leadership requires shifting from personally completing tasks to developing people, building systems and trusting teams to deliver results.
Perhaps most importantly, Simpson challenged business leaders to encourage others throughout their professional journeys — not simply celebrate them when they achieve major milestones.
She reflected on how quiet the encouragement can become during difficult business conditions, even when employees are working tirelessly toward improvement.
Her advice: Recognize effort, affirm people's capabilities and remind them that temporary setbacks do not define their careers.
Simpson concluded by encouraging attendees to take ownership of their professional development, surround themselves with supportive people and never allow others to define their potential.
Her journey from an entry-level employee to the CEO's office illustrates that leadership isn't necessarily about having all the answers. It's about remaining adaptable, taking calculated risks, investing in people and continually challenging personal limitations.
"Whatever you think you're capable of, there's at least one more stretch," she reminded attendees.
For women pursuing leadership opportunities throughout trucking, Simpson's message offered both inspiration and a challenge: Believe in your potential, prepare for change, and have the courage to pursue what's next.
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