AI Upended Our Product Roadmap. Here's How We Pivoted - and Kept Customers Bought In
A year ago, we faced a blunt reality: the SaaS platform we sold to sales engineers would be replaced by AI-native interfaces. Not incrementally. Completely. We had to rebuild our product from scratch and move customers to an entirely new way of working - without losing them.
The plan was simple in principle, hard in practice: deliver the same outcomes our customers paid us for (better sales productivity on complex deals), but let AI do the work instead of humans logging activity in software. That meant more impact, fewer clicks, and zero busywork.
Same outcomes, new interface
We weren't "adding AI features" to our existing platform. We were asking customers to adopt a brand-new, AI-native product that would replace long-standing workflows. The core promise stayed the same: help sales teams win faster and with less effort.
To make it stick, we went personal. Direct emails. LinkedIn messages. Zoom calls. The message: AI is a once-in-a-generation shift, and building for the past would waste your budget. We'll deliver the outcomes you bought us for - and more - in a new model built for what's next.
Three customer transition paths
Contracts made the shift real. Our customers paid per user, and their level of utilization dictated our approach. We created three clear paths:
- Fully utilized, high-dependency customers: Treat as a net-new cross-sell. Help them secure new budget for the AI platform while planning a staged sunset of the old system. We partnered on messaging to their leadership and budget owners.
- Partially utilized customers: Offer credits equal to unused licenses and use them to seed the AI platform with a forward-deployed team. Those early adopters became internal champions at renewal.
- Underutilized, low-change customers: Move spend from A to B. Turn off the SaaS tool, turn on the AI platform, run onboarding like a new deal. Fast and clean.
The result: more than 80% of customers transitioned or are in-flight. The business stabilized, and the product now aligns with how sales teams will actually work with AI.
What we learned
- Rip off the Band-Aid: The longer you wait, the harder the switch. We reassessed teams, reallocated talent, and parted ways where roles no longer fit the vision. We brought investors into the plan early and kept them close.
- Don't sugarcoat it: Straight talk with employees, investors, and customers kept trust high. We shared how we saw the market and why staying the course would fail them.
- Offer practical compromises: A rigid "take it or leave it" stance would have cost us good customers. Credits, phased rollouts, and clear sunset plans kept accounts intact through the change.
Unexpected upside: several customers who were planning to churn on the old product renewed - and expanded - on the AI platform. Same outcome, better path.
For sales leaders: how to run this play with your accounts
- Lead with outcomes, not features: Tie the new platform to deal velocity, win rates, and rep capacity. Keep it measurable.
- Segment by utilization and change effort: Map each account to one of the three paths above. Bring finance and ops into the conversation early.
- Create internal champions: Stand up a small team on the new platform ahead of renewal. They should own use cases that matter to leadership (RFPs, complex configurations, security reviews, pricing consistency).
- Budget narrative matters: Position the AI platform as a shift from manual process costs to automated outcomes. Ask for net-new budget with a clear sunset plan for legacy spend.
- Make the migration plan visible: Share timelines, milestones, and success metrics. Remove guesswork.
If you need market context to support the budget ask, point to independent data on AI's impact on sales productivity, like this analysis from McKinsey on generative AI in sales (read here).
Key takeaway
Don't wait for the axe to fall. If AI will obsolete your current workflow, rebuild now and bring customers with you. Offer a clear path, speak plainly, and keep the promise they originally bought - only delivered with less friction and more impact.
Upskilling your team on practical AI workflows for sales? Explore job-specific learning paths at Complete AI Training.
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