Ryan Massie

Ryan Massie

Director of Sales, President, Co-Founder

Hello, I’m Ryan Massie, the Co-founder and President of Syssero. In my role, I drive strategic growth and shape our brand within the expansive Workday® ecosystem. 

My professional journey to Workday® and Syssero ownership is unconventional to say the least. Nearly a decade ago, I transitioned from serving as a Professor of fine arts and communications at various higher education establishments around Chicago to the role of Technical Recruitment at Oxford International’s national office in the DFW Metroplex.  In this transition, I recognized the immense potential in the rapidly growing Human Capital Management (HCM) software landscape, particularly the revolutionary impact Workday® was poised to make. Acknowledging my ability to identify new markets and drive new revenue streams, Oxford International executives placed me in a leadership position within the Emerging Skills division. It was here that I was introduced to Amber Lowry, who would become my Business Partner at Syssero.

Amber and I aligned uniquely in purpose: advocacy for the human element behind the technology. This core is embodied in Syssero, from the design of our service offerings, our engagement protocols, and most evidently – the people we empower internally and externally. The most rewarding aspect of my job is the opportunity to help people, to respect complexity while simultaneously finding simplicity that’s actionable.

My areas of expertise include direct sales, sales training, relationship building, talent identification, business development, crafting essential business infrastructure, and strategizing effective go-to-market approaches. I’ve applied these strengths in strategic counsel to other Workday consulting firms and maintain strong relationships with Workday Regional Sales Directors, Customer Success Managers, Account Executives, Partner Execs, and many more.

Drawing from my background in arts education, I bring a unique, creative perspective in engagement: offering solutions and guiding our prospects/partners toward success.

On a more personal note, I’m an avid gardener, golf enthusiast, and I take great pride in being a father to my children, June and Sullivan. It’s great to meet you!