Turn Every Won and Lost Deal Into a Playbook for Your Next 10 Wins
By Stage 3, you’ve had real conversations, real demos, and at least a few wins and losses. Most teams move on and forget. Instead, we treat each deal as data. This engagement gives you a structured SaaS win loss analysis program that turns buyer feedback, sales notes, and competitor behavior into clear actions to improve close rates, sharpen messaging, and inform your roadmap.
Why Early-Stage Teams Waste Their Best Source of Insight
Most early-stage SaaS teams don’t truly know why they win or lose deals. They:
- Rely on gut feel from the founder or salesperson.
- Blame price, timing, or “no budget” without evidence.
- Never talk to prospects again after a loss.
- Have no central log of reasons for selection or rejection.
- Don’t connect deal outcomes back to ICP, messaging, or roadmap.
As a result, you repeat the same mistakes in every new opportunity. Your sales story drifts away from what buyers actually care about. Your product roadmap is guided by hunches instead of patterns, and forecasts from Stage 2 become less accurate over time.
Stage 3 fixes this by building a repeatable win loss feedback loop around your real deals.
What You’ll Have at the End of Stage 3
1. A Clear Picture of Why You Really Win
Not just “relationship” or “feature X.” You’ll see which ICP segments buy most and why, which problems you’re truly winning on, and which proof points matter in the final decision.
2. A Clear Picture of Why You Really Lose
Beyond “price” or “timing,” you’ll understand where your product is behind, where messaging or demo flow loses people, where competitors out-position you, and where you’re disqualified early.
3. A Deal Outcome Pattern Map
Patterns surfaced by ICP segment, use case, sales stage, and competitor, so you can separate one-off edge cases from systemic issues.
4. Messaging & Sales Motion Upgrades
Concrete improvements to discovery questions, qualification, demo storyline, objection handling, and proof points based on what buyers actually say.
5. Product & Roadmap Input
Evidence you can use to prioritize must-have features blocking deals, differentiate where you truly win, and stop over-building where it doesn’t matter.
6. A Simple, Repeatable Win Loss Process
A lightweight program your team can continue running after our engagement, so win loss becomes part of how you operate — not a one-off project.
What Stage 3 Includes
- Win loss interview guide tailored to your ICP and sales motion
- Completed buyer and lost-prospect interviews (live or async)
- Win / Loss Reason Coding Scheme (how we categorize outcomes)
- Deal Outcome Pattern Report (wins, losses, no-decisions)
- Competitor Insight Summary (when they win, why)
- Messaging & Sales Motion Recommendations
- Product & Roadmap Impact Brief
- Optional: Internal enablement deck to present findings to your team or board
How Stage 3 Works (Step-by-Step)
Step 1 — Program Design & Deal Selection (Week 1)
We align on goals, choose which recent wins, losses, and no-decisions to include, identify buyer roles, and define the questions that matter most to you.
Step 2 — Interviews & Data Collection (Weeks 1–3)
I conduct structured interviews with recent customers and lost prospects, and review CRM notes to connect qualitative feedback with deal data. Your team doesn’t have to chase or run interviews.
Step 3 — Analysis & Pattern Mapping (Weeks 3–4)
I synthesize reasons for win and loss, surface patterns by ICP, use case, competitor, rep, and stage, and distinguish systemic issues from one-off edge cases.
Step 4 — Working Session & Action Plan (Week 4)
We walk through everything together and translate insight into a 90-day action plan across messaging, sales process, ICP refinement, and roadmap priorities.
Optional Step 5 — Ongoing Program Setup: we define when to trigger outreach, who runs interviews, how to log patterns, and how often leadership reviews win loss insights.
Investment
Most Stage 3 engagements fall between $1,500 and $9,500, depending on:
- Number of interviews
- Number of ICP segments or use cases
- How many competitors you want covered
- Whether we build a full internal enablement deck
For early-stage, pre-revenue companies, we can structure payments across the engagement.
Who Stage 3 Is For
Perfect if:
- You’re pre-seed or seed with at least a handful of won and lost deals.
- Deals feel random and you’re not sure what’s really working.
- You suspect you’re losing for reasons beyond “price.”
- Your team has strong opinions — but no structured evidence.
- You want to improve close rates and inform Stage 4 enablement.
Not a fit if:
- You don’t yet have any serious deals or opportunities (Stage 1 or 2 comes first).
- You only want happy customer stories, not honest feedback.
- You see win loss as a one-time checkbox, not part of your learning loop.
What Founders Say
“Our team had lots of theories about why we were losing… and most of them were wrong. Stage 3 showed us the real patterns and helped us fix our sales story.”
Founder, Vertical SaaS (Seed Stage)
“The competitor insights we got from win loss were worth the entire engagement. We changed how we handle two critical objections and started seeing deals move again.”
CEO, Early-Stage AI SaaS
Ready to Learn From Every Deal Instead of Just Moving On?
Tell me about your current pipeline and close rates, and I’ll give you an honest view of whether Stage 3 is the right next step — or whether we should start with Stage 1 or 2 first.