Product Update: Win Loss Plus - Automatic Deal Classification

Knowing why you really win and lose deals has always been a problem. Reps have stories, management wants facts.

Our new Win Loss Advanced Agent now turns every Closed Won and Closed Lost HubSpot deal into a clear, objective view of what drove the outcome. It automatically groups those reasons so you can see the themes across all your wins and losses. No setup required.

What Gets Classified

For every closed deal, Win Loss Plus groups the contributing factors into three categories:

Sales Motions show what your reps did well or where they struggled. This includes things like value messaging, discovery quality, follow-up consistency, and qualification rigor. You can see which selling behaviors correlate with wins and which patterns keep appearing in losses.

Internal Assists and Blockers identify where your own organization helped or hurt the deal. Maybe marketing turned around content quickly, or an executive got involved at the right time. On the flip side, you might see delayed legal approvals or slow contract processes showing up repeatedly.

Customer Context captures the buyer's situation: their pain points, the compelling events that created urgency, and the stakeholders who influenced the decision. This tells you what actually motivated the purchase or what was missing when deals fell through.

These classifications are generated from your actual deal data and personalized to your company, product, and customers.

How Teams Use This

Coach with facts. Show reps which motions win and which patterns keep losing deals.

Ramp new reps faster. "Here's how we actually win deals here," backed by real data.

Fix internal bottlenecks. See where legal, approvals, or missing resources are repeatedly hurting your sales team.

Aim marketing at real buyer pain. Build campaigns around the actual pain points and compelling events that show up in your wins.

Run deal post-mortems. Turn every key deal into a clear storyline of what worked, what broke, and what you need to repeat or fix.

When you click into any deal, you see the detailed analysis with scores and descriptions for each classified factor.

Availability

Win Loss Plus is a paid add-on that requires an annual Data Parrot Pro subscription. Once enabled, the AI begins analyzing your historical deals immediately.

Get started with Win Loss Plus today by contacting us.