Sabrina Mackessy: Bridging Operations and Product Strategy at WellSky
Sabrina Mackessy brings a strong operational foundation and a passion for purposeful work to her role as a solutions manager on WellSky’s revenue cycle management (RCM) team. With nearly a decade of experience in home health agencies—working in almost every operational role outside of clinical care—she has a deep understanding of agency workflows, clinician needs, and the critical role technology plays in supporting daily operations.
She joined WellSky in 2018, starting in professional services. In that role, Sabrina traveled extensively to train clients, working directly with users to help them adopt and maximize the platform. This hands-on experience shaped her customer-focused approach and continues to inform how she thinks about product development. Over time, her operational background and client-facing experience led her into product management, where she now helps influence solutions at a broader, more strategic level.
Sabrina was initially drawn to WellSky by the opportunity for change and a strong connection to the company’s mission. Supporting those who care for patients gives her a sense of purpose, and the ability to impact patient lives at scale remains a key motivator. Transitioning from a travel-heavy, client-facing role into product management required her to build new skills in technical concepts, strategic planning, and cross-functional collaboration. Today, her professional focus includes product strategy and AI-driven features, while personally she continues to build confidence presenting in larger forums.
One of Sabrina’s most notable accomplishments is the successful introduction of patient account history, a project that delivered meaningful value to clients. While that milestone stands out, she is most proud of the strong collaborative relationships she has built across teams—partnerships she considers essential to delivering effective solutions.
Outside of work, Sabrina enjoys hiking with her dog, attending live music events, and reading—whether through a physical book or an audiobook. She spends her weekends exploring San Diego’s neighborhoods and restaurants and gravitates toward travel destinations that offer insight into everyday life and local culture. She feels fortunate to have explored much of the United States, as well as Asia, Europe, South America, and Central America.
Reflecting on her time at WellSky, Sabrina shares, “I’ve genuinely enjoyed my time here, mostly because of the people I work with every day. I’ve built strong relationships across teams, and there’s a culture of collaboration and problem-solving that makes even the tough days feel manageable. Being surrounded by teammates who care, communicate well, and support one another has made this a place where I’ve been happy to grow my career.”
