The Ultimate Landscape CEO - Jeffrey Scott Leadership & Growth Lessons from Aspire Software, with Mark Tipton and Eli Zevin
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Dec 9, 2025 Mark Tipton, co-founder and former CEO of Aspire Software, shares his journey transforming a skunkworks project into a leading platform for landscape management. Eli Zevin, the current General Manager, discusses his vision for integrating AI into Aspire's services for better customer success. They tackle leadership challenges, the importance of company culture, and simplifying client onboarding. Excitingly, Eli reveals plans for AI-driven churn prediction and proactive insights, showcasing how technology will reshape the landscape industry.
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Humble Skunkworks To Industry Platform
- Mark Tipton told how Aspire began as a skunkworks project in 2013 and grew from a version 1 that looked very different than today.
- He described partnering with Kevin Kehoe and building a product to up-level the entire landscape industry.
Industry's Hands-On Roots Shape Product Fit
- Mark fell in love with the landscape industry because its leaders were pragmatic, hands-on people who rose from the field.
- That cultural humility made the sector attractive and informed Aspire's mission and product design.
Kevin Kehoe's Lasting Cultural Legacy
- Mark described Kevin Kehoe's long illness and how his dedication and relationships shaped Aspire's culture despite his health struggles.
- He recalled Kevin's empathy, industry credibility, and how his passing marked a significant moment for the company.