Every sales team wants to know why they win deals—and why they lose them. But too often, the answers are buried in a mess of CRM notes, vague post-mortems, and dashboards that look pretty but don’t say much. If you’re in B2B sales and want real, practical insight into your win/loss trends, this guide’s for you. We’ll walk through how to actually use Insightsquared to cut through the noise and get answers that help you sell better.
Why Win/Loss Analysis Actually Matters
Let’s be honest: most teams talk about “learning from losses” but rarely do it well. Real win/loss analysis is about finding patterns—what’s consistently working, what’s not, and where your process is getting jammed up. It’s not about blaming reps or celebrating random wins. If you can nail this, you’ll see:
- Fewer avoidable losses (the “we never stood a chance” kind)
- Better forecasting (no more mystery whale deals)
- Smarter coaching and onboarding
- More deals moving, less time wasted
What Insightsquared Does Well (And Where It Doesn’t)
Insightsquared connects to your CRM and chews through your data to spot trends. It’s especially good at:
- Surfacing patterns over time: Not just “what happened last quarter,” but “what usually happens with deals like this?”
- Comparing win/loss factors: See which competitors, products, or deal sizes trip you up most.
- Highlighting pipeline health: Are you losing more late-stage deals? Is a certain team struggling?
But let’s keep it real: It won’t fix bad CRM data. If your notes are junk or reps fudge close dates, Insightsquared can’t magically clean that up. Also, it’s not a win/loss interview tool—so if you want verbatim customer reasons, pair it with real conversations.
Step 1: Clean Up Your CRM First (Seriously)
Before you even open Insightsquared, check your data. Most win/loss analysis fails because the underlying CRM is a mess. Make sure:
- Opportunity stages are accurate and consistently used.
- Close dates aren’t wishful thinking.
- Loss reasons are filled in—and not just “Price” or “Other.”
- Owners and products are correct.
Pro tip: Run a quick report in your CRM: Show all closed-lost deals from the last quarter and scan the notes. If you’re seeing lots of blank fields or copy-paste excuses, put a fix in place first. Otherwise, Insightsquared will just reflect that mess back at you.
Step 2: Connect Insightsquared to Your CRM
Assuming your data’s in decent shape, connect your CRM (Salesforce, HubSpot, etc.) to Insightsquared. The sync process is usually straightforward, but here are the things to watch for:
- Make sure you’re pulling in all relevant fields: stage, owner, close date, loss reason, product, competitor, deal size.
- Check how often data syncs—daily is fine for most teams.
- If you use custom fields for loss reasons or competitors, map them in the setup so you’re not missing key info.
Heads up: If you have multiple pipelines (e.g., SMB vs Enterprise), set those up separately. Otherwise, your trends will get muddied by apples-to-oranges comparisons.
Step 3: Get Oriented—Dashboards That Actually Matter
Insightsquared has tons of dashboards. Don’t get lost. For win/loss analysis, focus on:
1. Win/Loss by Reason
This shows why deals are being marked lost (or won). Look for:
- The top loss reasons—are they actionable? Or just “Budget” and “No Decision”?
- Any sudden changes over time. Did “Lost to Competitor X” spike recently?
- Which reps are using which reasons. (If one person marks everything “Other,” have a chat.)
2. Win/Loss by Deal Segment
Break it down by:
- Product or service line
- Deal size (small vs. large)
- Industry or vertical
You’ll spot patterns fast. Maybe you win small deals but lose big ones—or always lose in one vertical. That’s gold for focusing your sales strategy.
3. Sales Stage Dropoff
Where are you losing steam? Insightsquared can show you at which stage most deals die. If everything falls apart late, maybe your demos overpromise. If you never get past discovery, your targeting could be off.
4. Competitor Analysis
If you track competitors in your CRM, Insightsquared can show you who’s beating you (and where). Watch for:
- Competitors that keep popping up in losses
- Stages where you lose to them
- Any improvement (or worsening) trends over time
Ignore: Vanity dashboards. Some charts look slick but don’t help you take action. If you can’t explain what you’d do differently after seeing a chart, skip it.
Step 4: Dig for Real Patterns, Not One-Off Stories
It’s tempting to chase the last big deal you lost. Don’t. Use Insightsquared to look for:
- Trends across time (Do we always lose to Price at end of quarter? Is a certain competitor creeping up?)
- Patterns by rep (Is someone losing more than the team average? Or crushing it against a competitor?)
- Stages where things fall apart (Do we lose after demos? After legal? After pricing?)
Pro tip: Ignore outliers unless you see them repeat. One weird loss doesn’t mean you need a new playbook. Patterns are what matter.
Step 5: Take Action—And Track If It’s Working
Insightsquared gives you the “what,” not always the “why.” Once you spot a trend, do something about it:
- If “Lost to Competitor X” is rising, run a deal review: What’s their edge? Can you counter it?
- If “No Decision” is your top loss reason, your qualification process might be weak—or your solution’s not urgent enough.
- If a team member is always losing at a certain stage, coach them (and see if it improves over the next month).
Come back to Insightsquared after a quarter and check if your changes moved the numbers. If not, try something else. Don’t just admire the dashboard.
Step 6: Share Insights (But Skip the PowerPoint)
Don’t bury your findings in a 40-slide deck. Keep it simple:
- Share a screenshot of the key dashboard in Slack, with two lines of context.
- Bring a single trend to your next sales meeting and ask for ideas.
- Use real examples (anonymized, if needed) to spark discussion.
The goal: Get people talking about what’s actually working and what’s not. Don’t turn this into a data science project.
What to Ignore (And What to Watch Out For)
Not everything Insightsquared shows is worth obsessing over. Here’s what’s not worth your time:
- “Top Reps” leaderboards: These favor whoever got lucky with a few big deals. Focus on trends, not winners.
- Overly granular filters: If you slice data into a million segments, you’ll start seeing patterns that aren’t real.
- Charts with tiny sample sizes: If you only have 3 deals in a segment, don’t draw big conclusions.
Watch out for:
- Bad CRM habits creeping back in: Set a calendar reminder to check field completion once a month.
- Blaming the tool: If you don’t see actionable insights, the problem is usually in your process or data—not Insightsquared.
Wrapping Up: Keep It Simple and Keep Going
Insightsquared can help you spot real win/loss trends—if you focus on clean data, actionable dashboards, and using the insights to actually change what you do. Don’t overcomplicate it. Start small, look for patterns, and tweak your process. The more you use it, the sharper your instincts and your pipeline will get. And if something isn’t working? Change it up and check again. That’s how you get better, not just busier.