The problem

Before Hindsight, Simpro Group’s competitive intelligence and win-loss motions were manual, fragmented, and slow.

Competitive enablement relied on static battlecards and positioning docs that were expensive to maintain and often outdated by the time sellers needed them. Win-loss insights came from CRM dropdowns and email surveys, neither of which produced reliable or complete signal. Critical deal context lived in call transcripts, but extracting insights required ad-hoc analysis outside of core workflows.

As Simpro Group scaled across four brands and multiple regions, this approach became unmanageable.

“We needed to move past battlecards. Updating them across four brands took enormous effort, and they were usually outdated when sellers actually needed them.”

What Simpro Group was looking for

Simpro Group evaluated tools across competitive intelligence and win-loss, but most solutions focused on only one side of the problem or required expensive, slow, human-driven processes.

They were looking for a platform that:

• Unified competitive intelligence and win-loss in one system

• Scaled across brands, regions, and teams

• Delivered insights quickly enough to matter in active deals

• Was AI-forward and easy for sellers to actually use

Why Hindsight

Hindsight stood out early for its simplicity and usability.

Instead of forcing sellers and PMMs into new workflows, Hindsight met teams where they already worked—primarily Slack. The product felt intuitive, fast to adopt, and flexible enough to support real deal scenarios rather than generic battlecards.

“When we first saw Hindsight, it just clicked. It felt easy. It didn’t feel complicated to roll out or hard to explain to sellers.”

How Hindsight is used today

Simpro Group uses Hindsight across multiple teams:

Product marketing

• Query real deal data to understand what messaging works and why

• Generate competitive insights directly from calls and CRM data

• Replace static battlecards with dynamic, deal-specific guidance

Sales and BDRs

• Interact with Hindsight exclusively through Slack

• Ask real-time questions before, during, or after calls

• Get tailored guidance by competitor, industry, deal size, and use case

Enablement

• Train new sellers faster using real competitive scenarios

• Use AI roleplay to practice objection handling and demos

Product

• Identify feature gaps and roadmap signals directly from win-loss data

• Ground product decisions in quantified customer and prospect feedback

Marketing

• Analyze trends across lost deals, campaigns, and messaging performance

“The best competitive information doesn’t come from websites. It comes from real conversations sellers are having with prospects.”

Seller experience

Sellers don’t search for documents or leave their workflow. They ask questions in Slack and get answers grounded in Simpro Group’s own deal data.

“Reps can be on a call with Slack open and ask Hindsight how to handle an objection or how we compare in a specific scenario.”

This has directly improved both capability and confidence.

“You can hear it in their voice on calls. They’re more confident talking about competitors.”

Impact and ROI

Hindsight has delivered clear, measurable impact:

• Closed-won recovery: A ghosted prospect was re-engaged using an email generated with Hindsight and converted into a closed-won deal within a month

• Win-rate lift: Q4 closed-won rates increased by 10 percentage points compared to the prior nine months

• Pricing wins: Hindsight helped structure custom pricing terms that satisfied prospects while protecting margin

“Hindsight has been directly linked to deals we may not have closed otherwise.”

Executive adoption

Executives quickly adopted Hindsight due to its accessibility and clarity.

“When an exec first used the Slack bot, their reaction was ‘this is great.’ It was right there at their fingertips.”

Scaling across the business

Simpro Group began with one brand and is now expanding Hindsight across regions and all four brands.

Hindsight’s AI roleplay and competitive enablement tools help new sellers ramp quickly while maintaining consistency at scale.

“We’re able to scale competitive enablement across all our brands with a much lighter lift than traditional tools.”

Standout feature

When asked to name one standout capability:

“It’s the AI agent. It feels like ChatGPT, but it’s focused entirely on our competitive intel, win-loss data, and company context.”