The problem

Ironclad had a mature win-loss program, but it relied on expensive third-party interviews. That created three core issues:

• Tiny sample size: <5% of opportunities reviewed each month due to per-interview cost

• Stale insights: Interviews often happened months after deals closed

• Low flexibility: One-size-fits-all interviews couldn’t adapt to different deal scenarios

The result: high spend, limited signal, and reporting bottlenecks that slowed decision-making across PMM, Product, Sales, and Pricing.

Why Hindsight

Ironclad already had Gong and rich CRM data, but needed a way to systematically structure and analyze every deal, not just a sampled few.

Hindsight matched how the team wanted to operate:

• Leverage existing data (CRM + calls)

• Capture insight on 100% of opportunities

• Let teams self-serve answers instead of waiting on static reports

What they implemented

• Full-coverage win-loss analysis across all closed-won and closed-lost deals

• Structured deal attributes (use case, department, buying scenario) extracted automatically

• Self-serve reporting via chat for PMM, Product, Sales, and leadership

• Living documentation (ICP, messaging, battlecards) continuously updated from real deal data

The impact

From <5% to 100% deal coverage
Ironclad now has usable insight on every opportunity, with depth varying by deal stage—but no blind spots.

From static reports to interactive analysis
Instead of guessing the “perfect” report, teams ask their own questions and generate custom cuts instantly.

New dimensions of insight

• Win rates by deal scenario, not just segment or deal size

• Validation (and correction) of CRM fields reps previously filled manually

• Clear signal on which topics correlate with wins vs. losses—not just mentions

Cross-functional leverage

• Product: Ties feedback directly to outcomes, not just frequency

• PMM: Keeps ICP, messaging, and battlecards current with real data

• Sales leadership: Understands what actually moves deals forward

“We went from one very specific tool to something that helps in ten different areas—win-loss, competitive intel, pricing, and feedback extraction. The impact in just a few months has been pretty incredible.”

Who Hindsight is best for (in Ironclad’s words)

• Teams running traditional interview-based win-loss with small samples

• Companies with complex GTM motions: multiple products, segments, and personas

• Teams that want to move fast and share insights broadly across the company

Result:
Ironclad transformed win-loss from a narrow research function into a company-wide intelligence layer—grounded in real deals, available on demand, and tied directly to outcomes.