AI on the Right Side of the Bowtie

This research brief examines how AI is reshaping the right side of the Bowtie—onboarding, adoption, retention, and expansion—by turning unstructured customer data into expansion signals. Drawing on research conducted in Q2 2025 and validation across eleven AI-for-CS vendors, the brief explains why legacy health scoring models fail and how AI unlocks expansion by interpreting stakeholder sentiment, conversation data, product usage, and business context together. It introduces a maturity model from reactive to autonomous AI agents, outlines where expansion signals surface earliest, and provides a practical, phased roadmap for implementing AI as a revenue engine rather than a cost-saving tool.

Best For

• CEOs and founders scaling beyond $10M ARR where expansion drives future growth

• CROs, COOs, and revenue leaders seeking predictable Net Revenue Retention

• Customer Success and Account Management leaders shifting from retention to growth

• RevOps and CS Ops leaders architecting signal-driven post-sale systems

• B2B SaaS companies struggling to identify expansion opportunities early

• Organizations evaluating AI beyond task automation in post-sale motions

Key Takeaways

• Expansion revenue is the primary growth lever once ARR exceeds ~$10M.

• Traditional health scoring fails because it ignores context and intent.

• AI reveals expansion readiness by analyzing unstructured data at scale.

• Expansion happens when Impact is identified and amplified.

• The strongest results come from prescriptive and autonomous AI agents.

• Post-sale AI works best when treated as a strategic partner, not a tool.

Vendors Covered

• Aficio
• ChurnZero
• Cust
• DIVACS
• FunnelStory
• Gainsight PX
• OnRamp
• Radiant Point (Sky)
• Sunrise AI
• Totango
• Upollo
• UserGuiding