Jake Lisby, co-founder and CEO of Simplifyy, a property technology startup in Kansas City, Missouri, was both exhausted and exhilarated by the flurry of activity surrounding the pivot of the business model in late 2021. Simplifyy, a venture-backed PropTech company, was transforming from a full-service property management company to a pure SaaS player, selling end-to-end software to "simplify" the labor-intensive property management industry. Lisby, a Missouri native, knew that the change was not without its challenges. Running a software business in the Midwest, which lacked the entrepreneurial ecosystem of other well-known tech hubs, made it challenging to attract the necessary talent, customers, and fundraising. But the upside of pure SaaS company was attractive, and his team knew that not only to survive but to thrive, they had to get this right.