Meet Toby
Toby Massengale
Toby works with growth-minded landscape companies to turn software investments into real, lasting results. Too often, powerful tools are layered onto businesses that lack direction, alignment, and discipline leading to frustration, underperformance, and systems that never quite deliver on their promise. This challenge usually shows up at the intersection of vision, operations, systems, and leadership. Companies invest in software expecting transformation, but without shared direction, clear accountability, and consistent execution, even the best technology can’t do the heavy lifting
EOS & Operating System AlignmentWhy Operating Systems Matter More Than Software Alone
Toby believes deeply in the competitive advantage the right software can provide but he believes just as strongly that software can’t replace a solid operating system. Not the technology kind, the kind that aligns people, decisions, and execution around a common direction.
That perspective comes from firsthand experience. Toby owned and operated a successful landscape business for over 20 years and completed a successful exit in 2017. Along the way, he faced the same challenges many owners encounter: scaling operations, developing leaders, creating consistency, and turning growth into sustainable profit.
He was an early investor in Aspire Software and LandOne (prior to its acquisition by Aspire), and is currently an investor and partner in Operate.ai, an early-stage productivity platform, giving him a rare vantage point on both the promise and the limitations of business software.
EOS as the Foundation for Scale and Adoption
EOS, the Entrepreneurial Operating System, is a proven framework that helps companies get aligned around a shared vision, establish clear accountability, and build healthier, more effective leadership teams. For Toby, EOS isn’t an alternative to technology, it’s the foundation that allows technology to actually work.
When a business runs on a strong operating system, software stops being a struggle and starts becoming a strategic advantage.
How Toby Works With Leadership Teams
Toby works directly with leadership teams to install a clear operating system for the business, bringing structure to vision, discipline to execution, and strength to leadership. Once that foundation is in place, he helps ensure technology supports how the business actually runs, rather than forcing teams to work around their systems.
After working together, leadership teams are aligned, accountable, and healthy. The business operates with clarity and traction. Software investments finally deliver ROI. And owners regain confidence, control, and momentum, knowing their company is built to scale, perform, and win.