Profitable businesses with $10-30m ARR are targeted to industries where the Chicago firm can point to a specific edge (through a thesis, an executive on-boarded or past experience with similar challenges).
In this field, evaluation of AI opportunity and risk (and where the pendulum eventually swings) is crucial.
In this respect, Parker Gale have published an AI Resilience Scorecard (Summer 2026) to guide assessment. Things they look out for:
1. What cannot be copied - software is becoming easier to reproduce. Harder to copy are datasets, regulatory position, network, relationships.
2. Switching costs - can the company change its mind about its AI provider.
3. High retention not taken as proof of safety - not all organizations will willingly rip out their software and replace with an AI native version. However, the threat of AI-native competition will add pressure to pricing and scope.
AI implementation (and having AI-enabled features) is no longer a differentiating factor.
