Randolph (Randy) Guess

Randolph (Randy) Guess is a dynamic business and technology leader with extensive experience driving Go-to-Market (GTM) strategy, presales consulting, and professional services engagement within the enterprise ecosystem. As the Associate Vice President and Workday GTM & Alliance Leader at Jade Global, he spearheads the growth, bookings, and alliance strategy for the Workday North America practice. In this role, he leads the development of pricing models, sales messaging, practice readiness, and strategic enablement, collaborating across teams to deliver deep technical credibility and drive long-term, durable growth for clients.

Throughout his career, Randy has held senior leadership roles in partner and program management, presales, and solution architecture at industry-leading organizations, including Workday, Cognizant, Strada, Verizon, and Citibank. A certified Workday HCM professional, he has a proven track record of positioning the value of full-platform Workday solutions, building and managing portfolios of global and boutique partner system integrators, and leading high-performing pre-sales teams to secure medium and large enterprise deployments across diverse sectors, including Finance, Technology, Aerospace, Telecommunications, and Supply Chain.

Recognized for his ability to refine complex technical concepts into relatable, value-driven language for clients, Randy is passionate about fostering long-term partnerships and client satisfaction. Outside of his professional endeavors, he enjoys spending time with his family, exploring the great outdoors, and is based in the Dallas-Fort Worth area.