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Win/Loss Analysis

Systematic approaches to understanding why deals are won or lost and feeding insights back to product and GTM.

28 articles
Understanding 'No Decision' Losses: What Status Quo Wins Reveal About Your Value Prop

Understanding 'No Decision' Losses: What Status Quo Wins Reveal About Your Value Prop

Losing to competitors is frustrating. Losing to 'do nothing' is worse. Here's how to diagnose and overcome status quo bias through win/loss analysis.

November 22, 2025 7 min read
Competitive Displacement Patterns: What Win/Loss Reveals About Market Dynamics

Competitive Displacement Patterns: What Win/Loss Reveals About Market Dynamics

Win/loss data shows which competitors you're beating, which are beating you, and why. Here's how to identify displacement patterns and adjust strategy.

November 21, 2025 7 min read
Getting Brutally Honest Feedback from Lost Deals: Interview Techniques That Work

Getting Brutally Honest Feedback from Lost Deals: Interview Techniques That Work

Prospects who chose competitors rarely tell you the real reasons why. Here's how to conduct loss interviews that reveal truth instead of polite deflection.

November 19, 2025 7 min read
Building a Win/Loss Analysis Program From Scratch (Without a Team)

Building a Win/Loss Analysis Program From Scratch (Without a Team)

You don't need dedicated analysts to run effective win/loss programs. Here's how to build systematic deal intelligence with the resources you have.

November 18, 2025 7 min read
Recognizing Competitor Patterns in Win/Loss: What They Do When They're Winning

Recognizing Competitor Patterns in Win/Loss: What They Do When They're Winning

Every competitor has tells—tactics they use, messages they lead with, and plays they run when they're serious about a deal. Here's how to spot them.

November 1, 2025 7 min read
Running Cross-Functional Win/Loss Workshops That Actually Drive Alignment

Running Cross-Functional Win/Loss Workshops That Actually Drive Alignment

Win/loss insights sit across product, sales, and marketing. Workshops turn scattered findings into coordinated action—if you run them right.

November 1, 2025 7 min read
Automating Win/Loss Data Collection: What to Automate and What to Keep Human

Automating Win/Loss Data Collection: What to Automate and What to Keep Human

Automation can scale win/loss programs, but some parts of the process should never be automated. Here's where to invest in tools and where to stay manual.

November 1, 2025 7 min read
Win/Loss Analysis for Early-Stage Companies: Start Simple, Scale Smart

Win/Loss Analysis for Early-Stage Companies: Start Simple, Scale Smart

You don't need a formal program to learn from wins and losses. Here's how to extract insights when you're closing 5 deals a month, not 50.

November 1, 2025 7 min read
Win/Loss Interviewing: Uncovering the Objections They Never Told Sales

Win/Loss Interviewing: Uncovering the Objections They Never Told Sales

The real reasons you lost deals rarely appear in CRM notes. Here's how to structure win/loss interviews that get buyers to share what they actually thought.

November 1, 2025 7 min read
The Win/Loss Metrics That Actually Drive Better Decisions

The Win/Loss Metrics That Actually Drive Better Decisions

Most teams track win rate. The best teams track why win rate changes, which segments perform differently, and whether improvements stick.

November 1, 2025 7 min read
Using Win/Loss to Refine Product Positioning: What Buyers Actually Hear vs. What You Say

Using Win/Loss to Refine Product Positioning: What Buyers Actually Hear vs. What You Say

Your positioning deck says one thing. Buyers hear something completely different. Win/loss reveals the gap—and how to close it.

November 1, 2025 7 min read
Using Win/Loss Analysis to Validate (or Kill) Your Pricing Strategy

Using Win/Loss Analysis to Validate (or Kill) Your Pricing Strategy

Sales says you're too expensive. Buyers who chose you say price was fine. Win/loss data reveals which is true—and what to do about it.

November 1, 2025 7 min read
From Win/Loss Insights to Sales Coaching: Making Research Actionable

From Win/Loss Insights to Sales Coaching: Making Research Actionable

Win/loss analysis only matters if it changes how your team sells. Here's how to turn interview findings into coaching that actually improves win rates.

November 1, 2025 7 min read
Win/Loss Stakeholder Reporting: How to Make Research Findings Actually Matter

Win/Loss Stakeholder Reporting: How to Make Research Findings Actually Matter

Win/loss insights don't drive change unless the right people see them and act on them. Here's how to communicate findings so stakeholders actually care.

November 1, 2025 7 min read
Building a Win/Loss Taxonomy: How to Categorize Feedback You Can Actually Use

Building a Win/Loss Taxonomy: How to Categorize Feedback You Can Actually Use

Random win/loss notes don't drive decisions. A solid taxonomy turns anecdotes into patterns you can measure, track, and act on systematically.

November 1, 2025 7 min read
Quarterly Win/Loss Reviews: Turning Deal Data Into Strategic Action

Quarterly Win/Loss Reviews: Turning Deal Data Into Strategic Action

Most win/loss programs collect data but don't create change. Here's how to run quarterly reviews that turn deal insights into GTM improvements.

October 31, 2025 7 min read
Designing Win/Loss Surveys That Actually Get Honest Answers

Designing Win/Loss Surveys That Actually Get Honest Answers

Most win/loss surveys get polite non-answers. Here's how to design questions that surface the real reasons deals close or don't.

October 27, 2025 6 min read
Quarterly Win/Loss Reviews That Actually Change Behavior

Quarterly Win/Loss Reviews That Actually Change Behavior

I sat through quarterly win/loss reviews where everyone nodded, said 'interesting,' and changed nothing. Then I learned to run reviews that make people uncomfortable enough to act.

March 15, 2025 8 min read
Deal Forensics: Analyzing Complex Losses That Still Sting

Deal Forensics: Analyzing Complex Losses That Still Sting

We lost a $500K deal we thought we'd won. Six months later, I finally understood why. Here's how to do the forensic analysis that turns painful losses into strategic advantages.

March 12, 2025 9 min read
Win/Loss Program Setup: 30 Days from Idea to First Interview

Win/Loss Program Setup: 30 Days from Idea to First Interview

I pitched a win/loss program three times and got shot down twice. The third time, I stopped asking for permission and just started doing it. Here's the 30-day playbook that worked.

March 8, 2025 9 min read
Your First Win/Loss Interview: The Script I Wish I Had

Your First Win/Loss Interview: The Script I Wish I Had

I bombed my first win/loss interview so badly the customer asked if I was okay. Here's the script that turned me from nervous note-taker to insight-generating machine.

March 5, 2025 8 min read
Competitive Win/Loss Analysis: How to Learn Why You Win and Lose to Specific Competitors

Competitive Win/Loss Analysis: How to Learn Why You Win and Lose to Specific Competitors

You're losing deals but don't know why. Here's the framework for win/loss analysis that reveals competitive gaps.

July 12, 2024 8 min read
Win/Loss Analysis: The Framework for Learning from Every Deal

Win/Loss Analysis: The Framework for Learning from Every Deal

Most companies don't know why they win or lose deals. Here's how to build a win/loss program that actually improves win rates.

May 22, 2024 8 min read
Launching a Win/Loss Program as a Solo PMM

Launching a Win/Loss Program as a Solo PMM

I was the only product marketer, managing launches, sales enablement, and competitive intelligence. Building a win/loss program seemed impossible. Then I found a way to make it work.

April 20, 2024 9 min read
Turning Win/Loss Insights Into Sales Enablement That Actually Works

Turning Win/Loss Insights Into Sales Enablement That Actually Works

I spent six months conducting win/loss interviews and presenting insights to sales. Nothing changed. Then I learned the difference between sharing insights and enabling action.

March 29, 2024 8 min read
We Lost 15 Deals to the Same Competitor (Here's What I Learned)

We Lost 15 Deals to the Same Competitor (Here's What I Learned)

Losing repeatedly to one competitor felt personal. Then I analyzed every loss and found a pattern nobody expected—and a strategy that flipped our win rate.

March 7, 2024 9 min read
Building a Win/Loss Interview Methodology from Scratch

Building a Win/Loss Interview Methodology from Scratch

I had to build our first win/loss interview program with no budget, no precedent, and skeptical executives. Here's the methodology that finally got us real answers.

February 14, 2024 8 min read
Advanced Battlecard Strategies: How to Win Against Specific Competitors With Data-Driven Intelligence

Advanced Battlecard Strategies: How to Win Against Specific Competitors With Data-Driven Intelligence

Generic battlecards don't win deals. Here's how to build competitor-specific battlecards backed by win/loss data.

May 30, 2023 8 min read

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Launch planning, timing, and execution strategies that maximize impact and drive adoption.

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Crafting value propositions and messaging that resonates with buyers and differentiates from competitors.

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Proven frameworks, models, and methodologies that product marketers use to structure thinking, drive decisions, and execute consistently.

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Dashboard frameworks, attribution models, political navigation, and career strategies that help PMMs prove value and build executive influence.

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Q4 planning strategies, budget defense tactics, and ROI frameworks for protecting PMM resources during annual planning cycles. Navigate finance scrutiny and prove necessity.

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Practical guides for implementing the Pragmatic Institute framework, from market and focus to programs and readiness, helping PMMs get the most value from this popular methodology.

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