My guests today are Steve Lau and Rameez Ansari, co-CEOs of AutoLeap, a software company that services auto repair shops, that counts Bain Capital Ventures among its investors.

Prior to founding AutoLeap, Steve and Rameez purchased, operated, and sold D'Esco (later renamed FieldEdge), a software company that helps entrepreneurs run their HVAC, Plumbing, and Electrical Contracting businesses. Steve and Rameez purchased the company from its original founder in 2015 at 5X EBITDA, when its product was entirely on-premise and its revenue was generated solely through the sale of perpetual use licenses. After successfully transitioning the company to one that sold a cloud-based product and generated revenue on a subscription basis, they sold the company to a private equity firm for 8X revenue in 2019.

For the past 5-10 years, investors have salivated over the return potential inherent in transitioning a sticky enterprise software product with low customer churn from on-premise to SaaS. Though returns like those generated by Steve and Rameez certainly illustrate that such transitions can be successfully made, the headlines often ignore how brutally difficult this transition tends to be, both operationally and financially.

Though software investors and operators will find this episode relevant for what are probably obvious reasons, I’d also suggest that any CEO, in any industry, ought to pay attention to the lessons that Steve & Rameez learned, especially if they’re considering a transformation of any sort within their own companies. We talk about shifts in organizational culture, changes in salesforce compensation, how to communicate the need for change within a company, how to respect the history and legacy of a business while still keeping an eye towards the future, how non-technical CEOs can run a technically-oriented business, and much much more.