How PurpleLab Uses Hindsight to Turn Lost Deals into Strategic Wins
About PurpleLab
PurpleLab® is a health-tech company driven by one clear philosophy: outcomes matter most. We help organizations drive decisive action based on precise insights from real-world data – with the ultimate goal of giving everyone a fighting chance at the best possible health outcome.
Manual Win-Loss Processes Slowed Time-to-Insight
PurpleLab operates in a fast-moving and highly competitive market. The GTM team struggled to understand why they were losing deals—or what was driving repeatable wins. Despite having a CRM, post-mortem insights were buried, unreliable, or missing altogether.
Travis Allred, VP of Commercial Operations, described their win/loss insight process as “manual, inconsistent, and totally reliant on busy people entering clean data.”
“We’d lose a $400k deal and the reason logged in CRM would be ‘client not interested.’
They lacked a scalable process to analyze patterns across lost deals or escalate issues to product, enablement, or marketing teams. Feedback was anecdotal at best, and this lead to guesswork when teams were deciding strategy, roadmaps, and enablement plans.
“A lot of the learnings were just getting completely missed or thrown out."
From Haystack to Structured Insights
With Hindsight, PurpleLab deployed a workflow to automatically capture rep feedback, analyze transcripts, and summarize deal outcomes in the language their team actually uses.
“It’s comprehensive in how it captures context, but it gives me a clean summary and structured insights which I can act on fast.”
When deals close in PurpleLab's CRM, they are automatically imported to Hindsight for initial analysis. That includes calls, emails, notes, and relevant CRM fields.
Hindsight uses AI to review the deal for insights including:
Mentions of competitors
Sales or Pricing related Decision Drivers
Product and feature related insights
PurpleLab controls the list of competitors, Decision Drivers, and features that Hindsight reviews for.

Once Hindsight has an initial understanding of the deal, the AI interview reaches out to sales reps and SEs via Slack and/or Email to conduct personalized Win-Loss interviews. The interview questions are tailored to collect actionable feedback and insights based on the context of the deal.
They’ve now completed 100 AI post-deal interviews—automated, lightweight, and timely—giving them a consistent and scalable source of deal intelligence.
“The interviews are one of our favorite features. They happen in a timely fashion in Slack so reps still remember everything, they tease out useful insights, and they save everyone time. We now do this for all closed deals in important segments.”
This closed opportunity-to-insight loop ensures that the PurpleLab team is learning from each deal.

Quantifiable Insights, Aligned Teams
🔹 Surfacing Costly Product Gaps
“AEs kept saying we lost due to one missing data source. At first we thought they were exaggerating. But then we saw $7M in pipeline lost tied to that issue. That changed the conversation with Product immediately.”
🔹 Understanding Competitive Threats Earlier
“We noticed win rates dropped sharply the second certain competitors were mentioned. Hindsight helped us see that in many cases, we were being brought in as a backup—just to validate a decision they’d already made.”
This kind of pattern recognition changed how PurpleLab allocates presales effort, focuses prospecting, and engages earlier in the buying cycle.
🔹 Increasing Win Rates
PurpleLab's VP of GTM and Sales Enablement, Amy Crowe, shares that:
"Hindsight helps us run a consistent win-loss process without manual work. We get high-quality insights straight from the field and turn them into dashboards and insights that drive our strategy and help reps win more."
🔹 De-escalating Internal Conflicts
“There’s always friction between Sales and Product. But now we can go in and say, ‘Look at the data.’ That’s defused a lot of tension and helped everyone focus on the right priorities.”

Who Uses It?
Hindsight sits at the center of PurpleLab’s revenue operations team, but the insights are shared across sales leadership, product management, and marketing.
“It’s an operational hub. We boil down the insights so others can act—whether it’s changing messaging, coaching reps, or reprioritizing the roadmap.”
Why It Matters
Travis summed it up:
“We don’t miss intelligence anymore. We have assurance that if a deal can teach us something—win or lose—we’re capturing it.”