Her Story
About Karen
Karen Richardson is an accomplished customer support and healthcare technology leader with more than 14 years of experience in the healthcare SaaS industry. As Director of Technical Support at WebPT, she leads Tier 2 technical support operations, overseeing product onboarding, implementation, incident management, system monitoring, integrations, and product sunsetting. Known for her people-first leadership style, Karen combines technical expertise with empathy, clear communication, and process improvement to deliver exceptional customer experiences while empowering high-performing teams.
Karen's professional journey reflects resilience, adaptability, and continuous growth. She began her career as a general manager in the construction and fabrication industry before transitioning into healthcare after becoming a mother. Her entry into healthcare technology started with Strategic Healthcare Programs, where she supported executive leadership and sales operations while completing medical coding and billing training. She later joined Kinnser Software (now WellSky), steadily advancing from technical support to account management and customer success leadership. Her proven ability to improve onboarding, streamline workflows, reduce customer churn, and build collaborative teams led to multiple promotions before she joined WebPT, where she continued rising into senior leadership.
Committed to lifelong learning, Karen attended the University of Tennessee at Chattanooga, later earned a Bachelor of Arts in English, completed a Medical Coding and Billing program, and currently holds an associate degree while aspiring to pursue a master's degree in business. Throughout her career, she has remained passionate about improving healthcare technology through customer-centric innovation and operational excellence. Guided by values of accountability, empathy, punctuality, and continuous improvement, Karen is dedicated to helping healthcare organizations succeed while fostering an environment where both customers and employees can thrive.
Her Interview
Ten minutes with Karen
01What do you attribute your success to?
I attribute my success to the teams that I have built and the bosses I have had the privilege of working under. Their guidance helped me become comfortable as a people manager. I hate speaking in large crowds but enjoy hiring, coaching, and building high-performing teams that make me look good.
02What’s the best career advice you’ve ever received?
Put people first. Everybody is a person and has tough days, so take it with a grain of salt when someone is venting. Listen with empathy, which helps both team members and members have the best experience.
03What advice would you give to young women entering your industry?
After graduating high school in 1996, she attended the University of Tennessee at Chattanooga while exploring careers in healthcare. She later attended stenography school before earning a bachelor’s degree in Art and English. She also completed a Medical Coding and Billing program, knowledge she still uses to support her healthcare team. Today, she holds an associate degree and hopes to pursue a master’s degree, possibly in business.
04What are the biggest challenges or opportunities in your field right now?
The biggest opportunity right now is utilizing AI, which is huge and growing especially in documentation and healthcare space for time management. It creates opportunities for teams to learn, for me to build a larger team, and to be part of the growth and future of the industry.
05What values are most important to you in your work and personal life?
Accountability is essential - everybody makes mistakes but growth comes from identifying them, learning, and communicating openly. Punctuality is also key; being on time and showing up fully present is one of the most important signs of respect, especially in our busy digital-first world.
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