The Case For and Against Targeting a Software Company as a Searcher — What I Wish I Knew Earlier

Software has become one of the most popular — and most misunderstood — targets in the search fund ecosystem. In this session, Steve Divitkos (former searcher and software CEO) draws on firsthand operating experience, proprietary survey data, and a decade of market evolution to examine the real tradeoffs of targeting a software company as a searcher. The discussion goes beyond surface-level advantages to explore valuation dynamics, operational complexity, the feasibility of non-technical CEOs, and the very different “types” of software deals that exist under a single label. The goal is not to advocate for or against software, but to help aspiring searchers make a more deliberate, informed industry choice before committing years of their careers to it. Expect to Learn: • Has software always been popular in the ETA ecosystem? • How has its popularity trended over time? • The Suitability of Software as a Target for Searchers: Basic merits & risks • Can a Non-Technical CEO run a Software Company? • Detailed Comparison of Software Deals Against More “Typical” ETA Targets • Key Insights from the SaaS CEO Survey • 5 Very Different Approaches to Acquiring a Software Company • Given the rapid emergence of AI: Is software “dead”? • Sum it up: What does it all mean?