Her Story
About Jessalyn
Jessalyn Dickinson is a Learning Experience Designer, facilitator, and experienced people leader with more than 20 years of experience across retail, call center, customer care, and corporate environments. Based in Independence, Missouri, she specializes in creating practical learning experiences that improve decision-making, communication, leadership, and performance under pressure. She holds a Master of Science in Organizational Management from Ashford University, graduating with a 4.0 GPA, and has built her career around helping employees and leaders develop the skills and confidence needed to succeed.
Throughout her career, Jessalyn has designed and delivered training, onboarding, leadership development, and performance-support programs at organizations including CarMax, H&R Block, Dollar Tree, Walmart, and AMG Services. At H&R Block, she developed training programs supporting more than 5,000 employees across multiple vendors and lines of business, contributing to a 7% improvement in customer satisfaction. At Dollar Tree, she created leadership development programs that contributed to a 15% increase in store performance and developed a nearly 300-page manager training and how-to guide that was used across stores in the Kansas City area. Her experience also includes coaching managers, facilitating instructor-led and virtual learning, developing job aids and e-learning content, and supporting organizational change.
Jessalyn is particularly passionate about leadership development and believes strong performance comes from combining clear expectations, effective systems, practical training, and supportive leadership. She focuses on identifying performance gaps and translating business needs into learning solutions that employees can apply in real-world situations. Her areas of specialization include learning and development, instructional design, leadership development, executive coaching, employee engagement, performance management, organizational development, and business process improvement. She is also interested in helping teams strengthen decision-making under pressure, reflected in her development of Decision Dynamics, an interactive approach focused on understanding and improving how teams operate in challenging situations.
Her Interview
Ten minutes with Jessalyn
01What do you attribute your success to?
Chocolate is the secret to my success because I like to make things as fun as possible at all times. I would roll around in my chair at work and pop quiz my newer employees on different parts of the job and give them candy if they answered right. I created games like deal or no deal for enrollments where they could win money or chocolate. Ultimately it is about fun which builds rapport and morale.
02What’s the best career advice you’ve ever received?
The Stephen Covey Rocks video about prioritizing tasks transformed how I manage my work. When I was almost written up for not being productive despite working hard, another manager showed me the video and I created a spreadsheet called my rocks that I still use today for prioritizing both professionally and personally.
03What advice would you give to young women entering your industry?
Just ask questions. Whether to understand how to do the job or as a leader to understand why someone made certain choices. I learned this the hard way when I almost gave a wrongful write-up due to a misunderstanding without asking questions first.
04What are the biggest challenges or opportunities in your field right now?
Finding employees and especially motivated ones is a huge struggle in retail. Finding ways to motivate people is a big part of a manager's job because every person is different and chocolate does not work for everybody.
05What values are most important to you in your work and personal life?
Honesty, integrity, accountability, treating people with respect, doing the right thing even when it is not the easiest, holding myself accountable for impacts on others, and growth through learning and wanting to be better.
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