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“If you don’t have normalization of the metadata across the application layer, you cannot create the right systems of record to drive your systems of action.”

In this episode of Revenue Engine Masters, I sat down with Cliff Simon, founder & CEO of Polaris and one of the most thoughtful operators in the RevOps ecosystem. We went deep on the big shift happening in go-to-market: AI is forcing companies to confront their foundations—metadata, systems of record, systems of action—because bad data now leads to sh*ttier outcomes, faster.

Cliff breaks down why AI readiness is no longer a RevOps-only problem, but a company-wide mandate increasingly driven by CIOs, CFOs, and cross-functional leaders trying to decide what to build, what to buy, and how to ensure their teams are actually enabled.We explored how Polaris is helping companies navigate this moment with two offerings—AI Readiness Audits and GTME-as-a-Service—and why the new generation of AI-native GTM operators needs both strategic oversight and architectural guardrails.

He also shares how to build frictionless B2B buying experiences, the same way consumers buy: with credibility, simplicity, and trust.We closed by discussing speed vs. quality in building AI systems, the importance of doing work manually before automating it, and how to think about the emerging role of autonomous workflows. A super relevant conversation for anyone building GTM teams in 2025.