Karen T. Pickard
Karen T. Pickard is an accomplished HR and onboarding professional with over two decades of experience in client services, payroll, and employee integration. Currently serving as the Supervisor of Middle Market Onboarding at Insperity, she leads large clients through complex HR and payroll transitions, ensuring smooth implementation with both precision and care. Her journey with Insperity began as a client drawn to the company’s vibrant culture, and she has since built a career marked by dedication, growth, and a passion for helping others succeed.
Karen’s professional path is defined by resilience and vision. After an early role as a Payroll Specialist and later a Customer Service Specialist, she transitioned into middle market onboarding, where she quickly became a trusted guide for clients. In April 2020, she was promoted to Supervisor—a role she identified as essential within the organization. Beyond her formal responsibilities, Karen has earned recognition for her leadership and excellence, including Insperity’s 2017 Employee of the Year award, highlighting her impact both internally and externally.
An intellectually curious and passionate leader, Karen thrives on coaching her team, fostering collaboration, and cultivating meaningful client relationships. She balances her professional achievements with a commitment to her family, having navigated a career break with focus and determination. At her core, Karen’s success is fueled by a genuine love for helping people, a drive to innovate, and an unwavering dedication to excellence in every aspect of her work.
What do you attribute your success to?
I attribute my success to a combination of dedication, passion, and a genuine love for helping others. My journey with Insperity began as a client, drawn to the company’s vibrant culture, and has grown into a fulfilling career. I took a brief break to raise my family, and returning to the company allowed me to approach my work with renewed focus and energy.
Today, as the Supervisor of Middle Market Onboarding—a role I identified as a need and was promoted to in April 2020—I guide large clients through their HR and payroll integration with both expertise and care. One of my proudest achievements has been transitioning from an individual contributor to a leadership role, a journey that complements honors like my 2017 Employee of the Year award.
At the heart of my success is my passion for the company and my commitment to helping people—clients and colleagues alike—navigate new beginnings with confidence and support.
What advice would you give to young women entering your industry?
My advice to young women entering this industry is simple: be true to yourself. Don’t let anyone tell you that you can’t do something you want to do—because you absolutely can. I’ve lived this advice throughout my career, and it continues to guide me as I lead and support my teams. I take pride in helping others grow while also building my own path, and I hope to inspire the same confidence and determination in the next generation of leaders.
What values are most important to you in your work and personal life?
The values that guide me in both my work and personal life are integrity, dedication, and a genuine commitment to helping others succeed. I strive to approach every challenge with honesty, care, and a focus on growth—for myself, my colleagues, and the clients I serve.
Outside of work, I love camping and traveling, embracing new experiences and adventures whenever I can. I’ll always be a Buckeye at heart, and my family and I make it a point to attend a football game every year to celebrate that connection. These hobbies keep me grounded, energized, and connected to the people and passions that matter most to me.