How Gainsight Leverages Win/Loss Analysis with IcebergIQ to Drive Growth
At this year’s Pulse conference, a fireside chat between Natasha Narayan, CEO of IcebergIQ, and Jason Hersh, Principal, Market Intelligence at Gainsight, highlighted a powerful truth: companies that deeply understand why they win, lose, or churn are better equipped to grow.
From Gut Feel to Ground Truth
Many SaaS companies may think they know why customers make buying decisions, but the reality is often murkier. In an IcebergIQ survey, only 24% of customer success professionals said they felt confident they knew why their customers churned. CRM notes and CSM anecdotes aren’t enough. As Jason pointed out, “Sometimes people are afraid to tell you the truth.”
That’s why Gainsight partners with IcebergIQ to conduct one-on-one customer interviews. These conversations reveal the “why behind the why”– the factors that rarely show up in dashboards or forms.
Real-Time Activation Across the Business
Once an interview is complete, IcebergIQ delivers findings directly into a shared Slack channel. Gainsight invites stakeholders from sales, marketing, product, customer success, and even executives to access and engage with the findings immediately.
“We don’t just collect data. We activate it,” Jason said. “It may not be just about sales — it could be a feature gap or a service experience. We want the whole organization to learn from that.”
This distributed access allows Gainsight teams to respond quickly and effectively to emerging patterns.
Adding AI
Gainsight takes things a step further by integrating AI into the analysis workflow. Jason has trained custom GPTs using interview transcripts from IcebergIQ—separating them by product line for precision. With these models, his team can:
Search for themes across interviews
Build competitive battle cards
Draft tailored sales messaging
Support reps in live deal cycles
By layering interview insights with internal data and buyer intent signals, Gainsight generates highly personalized intelligence that’s accessible company-wide.
Natasha noted that while AI offers powerful tools for analysis and content creation (like summarizing insights into podcast-style briefings), human oversight remains critical. “AI doesn’t always catch nuance. We still review everything manually before it goes to clients.”
Executive Buy-In Improves Program Success
One key success factor? Leadership engagement. Gainsight CEO Nick Mehta listens to every interview. “It’s one of the highest-ROI things we’ve done,” Nick shared in a video message. “We’ve conducted hundreds and hundreds of interviews with IcebergIQ. For me, it’s super important as a CEO to always be learning. I want to learn how we can serve our customers better, how we can make our product better, how our team can be better.”
This top-down commitment ensures the insights aren’t trapped in a silo. Gainsight also holds quarterly QBRs with IcebergIQ, bringing executive teams into the conversation and holding teams accountable for acting on what’s learned.
Overcoming Challenges: Bookings, Incentives, and Data Integration
Recruiting interview participants can be tough, especially in today’s noisy market. IcebergIQ combats this with highly personalized outreach and, in some cases, increased incentives. Gainsight has also found success by having prominent internal leaders, like Nick, send the invitations directly.
Data fragmentation is another common challenge. Jason is manually pulling together insights from IcebergIQ, Gong, Klue, CRM systems, and internal win/loss notes to build a unified picture. “It’s messy,” he said. “But the data is there. You just have to roll up your sleeves.”
Bottom Line: Win/Loss Drives Results
By treating win/loss and churn analysis as a continuous, high-priority program, Gainsight is able to improve sales effectiveness, build more informed product roadmaps, and maintain competitive agility across their expanding suite of products.
The message was clear: If you want to grow, you have to listen to your customers, deeply and continually. See the full conversation here.