By Matt Darrow
About a year ago, my co-founders and I faced a critical challenge: AI was poised to make our SaaS platform for sales engineers obsolete. Our current product was designed for a world that was quickly evolving toward AI-native interfaces, rendering the existing workflows unsustainable. To survive, we needed to rebuild from scratch and transition our customers to an entirely new AI-native system that could deliver the same outcomes, but more efficiently.
Instead of merely upgrading our software with AI features, we created a new vision that matched our ideal customer profile and continued solving their core problem—enhancing sales productivity for complex product teams. I personally reached out to customers through emails, LinkedIn messages, and Zoom calls to explain this major pivot and reassure them.
We segmented our customers based on their usage levels and tailored transition strategies accordingly: heavily utilized customers underwent a net new sales process to secure budgets, moderately utilized customers received credits to balance new subscriptions, and smaller, nimble customers simply transitioned spend from the old to the new platform. Over 80% of our customers have now transitioned or are in the process of doing so.
Key lessons we learned included making decisive changes early, being honest and transparent with all stakeholders, and finding compromise solutions rather than a rigid approach to retain customers during upheaval. Ultimately, the transition not only stabilized our company but also led some customers to expand their use of our new AI platform upon renewal.
Matt Darrow is CEO and co-founder of Vivun, the AI sales teammate, and a prior leader at Zuora.
Illustration: Dom Guzman
