The VP of Sales asked me to "figure out why we're losing deals" during a hallway conversation on Wednesday. By Friday, he wanted an update on my progress.
I was the only product marketer at a 75-person SaaS company. My responsibilities already included product launches, sales enablement, competitive intelligence, website messaging, customer case studies, and analyst relations.
Now I was supposed to build and run a win/loss program too.
I had no budget for third-party interview firms. No bandwidth to conduct dozens of interviews myself. No analyst to help with data analysis. Just me, my existing workload, and an expectation that I'd somehow systematically interview buyers and uncover why our win rate had dropped from 47% to 34%.
Building a win/loss program as a solo PMM felt impossible. Then I stopped trying to build the "perfect" program and started building the program I could actually sustain.
The Reality of Solo PMM Win/Loss Programs
Every article about win/loss programs assumes you have resources:
"Conduct 50-100 interviews per quarter for statistical significance."
"Partner with a third-party firm to eliminate bias."
"Build a dedicated team for win/loss analysis."
That's not reality for solo PMMs. Our reality is:
Limited time: maybe 5-8 hours per week if you're lucky.
Zero budget: can't afford $300/interview third-party firms.
No team: you're doing recruitment, interviews, analysis, and distribution alone.
Competing priorities: launches and sales enablement can't stop while you build a win/loss program.
I needed a program that worked within these constraints, not in spite of them.
The Minimum Viable Win/Loss Program That Actually Worked
I built the simplest sustainable program possible:
Target: 8 interviews per month (2 per week)
Not 50 interviews per quarter. Not 100. Just 8. Two wins, six losses.
This was manageable. Two hours of interviews per week, one hour of synthesis, 30 minutes of sharing insights. Total time commitment: 3.5 hours per week.
Focus: Recent competitive losses only
I couldn't interview every deal. So I focused on competitive losses from the past 30 days over $25K. This gave me the highest-signal insights with the least effort.
Wins were nice to understand, but losses revealed what we needed to fix urgently.
Automation: CRM trigger + template emails
I set up a Salesforce workflow: when an opportunity marked "Closed Lost - Competitor" over $25K closed, I got an automated email with the contact information and deal details.
I created three template emails for recruitment that I could customize in two minutes. No starting from scratch each time.
Incentive: $50 gift cards
I negotiated $400/month budget (8 interviews × $50). Small enough to get approved, large enough to drive 35-40% response rates.
Format: 30-minute calls, recorded and transcribed
I used Zoom for interviews and Otter.ai for transcription. This meant I could focus on listening instead of note-taking, and I had verbatim quotes to share with stakeholders.
Distribution: Weekly Slack post, monthly summary
Every Friday, I posted one key insight from that week's interviews in our sales Slack channel with a 60-second clip from the interview.
Every month, I sent a 2-page summary to leadership with patterns across all interviews.
This program was small, focused, and sustainable. And it worked.
How I Fit Win/Loss Interviews Into My Existing Calendar
The hardest part of launching a win/loss program as a solo PMM isn't the methodology—it's finding time when you're already stretched thin.
Here's how I made it fit:
Monday morning: 30 minutes for recruitment
I checked the automated Salesforce notifications from deals that closed the previous week. I sent recruitment emails to 4-5 prospects using my templates.
This took 15-20 minutes once I had templates dialed in.
Tuesday and Thursday afternoons: Interview slots
I blocked 2pm-3pm on Tuesdays and Thursdays for win/loss interviews. Most prospects could accommodate afternoon calls.
If nobody booked those slots, I used the time for other PMM work. If someone booked, I had the time protected.
Friday morning: 30 minutes for synthesis and sharing
I reviewed that week's interview transcripts, pulled one key insight, grabbed a 60-second video clip, and posted it in Slack.
This took 20-30 minutes and kept insights top-of-mind for sales.
Last Friday of month: 90 minutes for monthly summary
I compiled the month's interviews into themes, identified top 3 patterns, and wrote a 2-page summary with recommendations.
Total monthly time commitment: ~14 hours (3.5 hours per week).
That's sustainable for a solo PMM managing multiple responsibilities.
The First Month's Results (Even With Just 8 Interviews)
I completed 7 interviews in my first month (one prospect canceled last minute).
Even with a small sample, patterns emerged:
Pattern 1: We were losing to competitor X in 5 of 7 losses
This focused our competitive response. We weren't losing to the market—we were losing to one specific competitor.
Pattern 2: Buyers mentioned implementation concerns in 6 of 7 interviews
"We weren't confident you could get us live in our timeline" appeared repeatedly. This wasn't about product features—it was about implementation trust.
Pattern 3: Sales reps were leading with features, buyers were buying based on business outcomes
Disconnect between how we sold and how buyers evaluated.
Seven interviews. Three actionable patterns. One month.
The VP of Sales who'd asked me to "figure out why we're losing deals" read my first monthly summary and immediately scheduled a sales training session on implementation messaging.
Small sample size, big impact.
The Recruitment Email Template That Got 40% Response Rates
Most prospects ignored my initial recruitment emails. Then I tested variations and found a template that consistently got 40%+ response rates:
Subject: Quick feedback on your [Product Category] evaluation - $50 thank you
Body:
Hi [Name],
I'm [My Name], on the product team at [Company]. You recently evaluated [product category] solutions and chose [Competitor].
I'm researching how buyers make decisions in this space to improve our product and customer experience. Would you be open to a 30-minute call sharing your perspective?
This isn't a sales call—we genuinely want to learn what went well and where we can improve. As a thank you, I'll send a $50 Amazon gift card.
[Calendar link]
Thanks for considering, [My Name]
What made this work:
Clear subject line with the incentive upfront.
Positioned as product research, not sales follow-up.
Acknowledged they chose a competitor (removed defensiveness).
Specific time commitment (30 minutes).
Clear incentive ($50).
One-click scheduling (calendar link).
I tested versions without the incentive (15% response rate), versions with $25 incentive (28% response rate), and versions with $50 (41% response rate).
The $50 threshold mattered for busy decision-makers.
The 5-Question Interview Framework for Time-Constrained PMMs
I didn't have time for 60-minute comprehensive interviews. I needed maximum insight from minimum time.
This 5-question framework consistently revealed actionable insights in 30 minutes:
Question 1: "What prompted you to look for a [product category] solution?"
This uncovered trigger events and buying urgency. Understanding what made the problem urgent informed our demand gen and sales approach.
Question 2: "Walk me through your evaluation process. Who did you look at and how did you compare them?"
This revealed actual decision criteria vs. what we assumed mattered. Buyers rarely evaluated products the way we thought they did.
Question 3: "What were the top three factors in your final decision to choose [competitor]?"
Direct question about competitive differentiation. Buyers were surprisingly candid.
Question 4: "What could we have done differently to win your business?"
This surfaced specific gaps—product features, sales approach, pricing, implementation concerns. Most buyers gave tactical feedback here.
Question 5: "If we addressed those gaps, would you consider us in the future?"
This qualified whether lost deals were permanently lost or recoverable opportunities.
Five questions. Thirty minutes. Actionable insights every time.
How I Scaled Analysis Without an Analyst
I was doing recruitment, interviews, transcription, analysis, and distribution alone. Analysis was the bottleneck.
Here's how I made it manageable:
Use Otter.ai for automatic transcription
Instead of manually transcribing or taking detailed notes, I recorded calls (with permission) and let Otter auto-transcribe.
This gave me searchable transcripts I could review in 10 minutes instead of 45-minute manual transcription.
Tag themes while listening, not after
During interviews, I kept a running list of themes in a Google Doc. When a prospect mentioned implementation concerns, I tagged it immediately.
After the interview, I just reviewed my theme tags instead of re-listening to the entire call.
Look for repetition, not statistical significance
With 8 interviews per month, I couldn't claim statistical significance. But I could spot patterns.
If 5 of 8 prospects mentioned the same concern, that was a pattern worth addressing, regardless of sample size.
Focus on actionability, not comprehensiveness
I wasn't trying to understand every factor in every deal. I was trying to find the top 2-3 patterns we could actually fix.
Analysis got easier when I stopped trying to be exhaustive and started focusing on what was actionable.
For solo PMMs looking to automate more of this workflow, platforms like Segment8 can help with pattern recognition and synthesis across interviews without requiring dedicated analyst time.
The Monthly Summary Format That Actually Got Read
My first monthly summary was 8 pages. Nobody read it.
My second was 2 pages with this structure:
Page 1: Top 3 Patterns
Pattern 1: What we heard repeatedly + Quote from buyer + Business impact
Pattern 2: Same structure
Pattern 3: Same structure
Page 2: Recommended Actions
Action 1: What to do + Who should own it + Expected impact
Action 2: Same structure
Action 3: Same structure
This format took 30 minutes to create and actually got read by executives.
The VP of Sales started forwarding my monthly summaries to the full sales team. The CEO asked to add me to the monthly board prep meeting to share competitive insights.
Two pages, three patterns, three actions. That's what busy stakeholders could consume.
The Resistance I Hit (And How I Overcame It)
Resistance 1: "8 interviews isn't enough to draw conclusions"
Some stakeholders questioned whether 8 monthly interviews provided meaningful insights.
My response: "You're right that it's not statistically significant. But when 6 of 8 prospects mention implementation concerns unprompted, that's a signal worth investigating. Would you rather wait six months for 100 interviews, or act on early patterns now?"
Early patterns beat delayed comprehensiveness.
Resistance 2: "We need a third-party firm to eliminate bias"
Sales worried I'd be biased conducting interviews as an internal person.
My response: I positioned myself as product research, not sales. I shared actual interview transcripts showing prospects were candid. I had sales reps listen to recorded calls so they could hear buyer feedback directly.
Trust built over time as insights proved valuable.
Resistance 3: "You don't have time for this on top of your existing work"
My manager worried the win/loss program would pull me away from launches and enablement.
My response: "I'm spending 3.5 hours per week. We're spending way more time guessing why we lose deals and building the wrong enablement. This program will actually make my other work more effective."
I tracked time spent and showed that win/loss insights reduced wasted effort on low-impact enablement.
The Results After Six Months
Interviews conducted: 47 (target was 48)
Patterns identified: 12 major themes across competitive positioning, sales process, product gaps, and implementation
Actions taken: 8 specific changes to sales enablement, 4 product roadmap shifts, 2 pricing/packaging updates
Win rate improvement: 34% to 42% over six months
Time investment: Average 3.8 hours per week
The program was small, focused, and sustainable. And it drove measurable improvement in win rates.
The Program I Wish I'd Built From Day One
If I were launching a solo PMM win/loss program again, I'd make three changes:
Start with wins, not just losses
I focused exclusively on losses initially. But interviewing wins revealed what we were doing right, which was just as valuable for sales enablement.
I'd allocate 2 losses + 1 win per week instead of 2 losses only.
Involve sales in interview selection
I selected which deals to interview based on deal size and timing. But sales reps could identify which losses were most confusing or unexpected.
I'd have sales nominate 2-3 deals per week for interview consideration.
Create a shared insight repository
I posted insights in Slack and sent monthly summaries. But there was no central place where sales could search historical insights.
I'd create a simple Notion database where every interview insight was tagged and searchable.
The Uncomfortable Truth About Solo PMM Win/Loss Programs
Most articles about win/loss programs are written by PMMs at well-resourced companies with dedicated teams and six-figure budgets.
That's not reality for most of us.
Solo PMMs don't have the luxury of perfect methodology. We have to make tradeoffs:
Small sample sizes vs. no data at all.
Internal interviewer bias vs. no interviews.
Simple analysis vs. comprehensive analysis we don't have time for.
The perfect win/loss program you never launch is less valuable than the imperfect program you actually run.
I started with 8 interviews per month, simple questions, basic analysis, and two-page summaries.
It wasn't perfect. But it uncovered patterns that improved win rates by 8 percentage points in six months.
That's better than the comprehensive program I never had time to build.
Quick Start: Launch Your Solo PMM Win/Loss Program in 2 Weeks
Week 1: Setup
Day 1-2: Get approval for $400/month interview incentive budget
Day 3: Set up Salesforce trigger for competitive losses over $25K
Day 4: Create recruitment email templates (customize my template above)
Day 5: Block Tuesday/Thursday 2pm-3pm for recurring interview slots
Week 2: Launch
Day 1: Send recruitment emails to 5 recent competitive losses
Day 2-4: Conduct first 2-3 interviews
Day 5: Post first insight in sales Slack channel
After 30 days: Send first monthly 2-page summary to leadership
You don't need a perfect program. You need a sustainable program that reveals patterns and drives action.
Start small. Start now. Iterate based on what works.
The companies with systematic win/loss programs aren't smarter or better-resourced. They're just the ones that started.