Analyze · Win/Loss Analysis

Compare Won vs Lost Deal Profiles

Side-by-side profile of your won vs lost deals so you can see exactly where the two cohorts diverge.

managerfounderIntermediate2 hours
When to use
Use when you have a balanced set of won and lost deals (at least 5 of each) and want a clean cohort comparison rather than a full narrative readout. Helpful right before tightening ICP or rewriting qualification criteria.
The prompt
You are an analytics-minded sales leader for a digital marketing agency. You build cohort comparisons using only the data provided and you call out where the data is too thin to conclude.
Agency: [AGENCY_NAME] — [SERVICES] | Period: [PERIOD] | Data:
[DEAL_LIST]
(Include for each deal: industry, company size, deal size, service requested, lead source, sales cycle days, decision-maker title, won/lost.)
Build a side-by-side profile comparing won deals vs lost deals across firmographics (industry, size), deal shape (service, ACV, cycle), and engagement (source, decision-maker level). Surface the 3 dimensions where the two cohorts diverge the most and what that implies about who we actually sell well to.

- Cite specific deal names when calling out a divergence.
- Note any dimension where either cohort has fewer than 4 deals as "low confidence."
- Do not infer fields that aren't in the input.
- Avoid language that blames individual reps.

Output a single comparison table with rows for each dimension and columns for Won Profile / Lost Profile / Divergence Notes. End with a 3-bullet "what this means for ICP" summary.
Variables
  • [AGENCY_NAME] — Your agency name
  • [SERVICES] — Service lines included
  • [PERIOD] — Date range being analyzed
  • [DEAL_LIST] — Closed deals with firmographic and deal-shape fields
Example input
Agency: Northstar Digital — SEO, Paid Search | Period: H1 2026
Deals:
FitGear Co | DTC apparel | 80 emp | $4.8k/mo | SEO | Referral | 18d | Founder | Won
PeakPet | DTC pet | 60 emp | $5.2k/mo | SEO | Referral | 21d | Founder | Won
Solavida | DTC wellness | 120 emp | $11k/mo | SEO+PS | Referral | 27d | CMO | Won
BrewHaus | B2B SaaS | 400 emp | $6k/mo | PS | Inbound | 41d | Demand Gen Mgr | Lost
MetroMattress | Retail | 900 emp | $9k/mo | PS | Inbound | 38d | Marketing Dir | Lost
Lumen Lighting | B2B mfg | 350 emp | $32k proj | Web | Outbound | 62d | VP Marketing | Lost
Example output
Comparison table:
Industry — Won: DTC consumer (FitGear, PeakPet, Solavida). Lost: B2B/large retail (BrewHaus, MetroMattress, Lumen). Divergence: strong; we win DTC, lose B2B.
Company size — Won: 60–120 emp. Lost: 350–900 emp. Divergence: clear up-market gap.
Service — Won: SEO-led. Lost: PS-led + Web. Divergence: SEO is our wedge.
ACV — Won avg $7k/mo. Lost avg $9k/mo + project. Divergence: we lose bigger deals.
Source — Won: 100% referral. Lost: inbound/outbound. Divergence: cold motions underperform — low confidence, only 6 deals.
Decision-maker — Won: Founder/CMO. Lost: Director/Manager. Divergence: senior buyers close.

What this means for ICP: (1) DTC consumer 50–150 emp is our true sweet spot. (2) SEO is the wedge — lead with it. (3) Push outbound to founder/CMO level only.
Pro tips
  • Add a "deal age in days" column — cycle length differences are often the most actionable signal.
  • Re-run quarterly and watch divergence widen or narrow — that's your ICP focus working or drifting.
  • If a cohort is too thin, broaden the period rather than guessing — Claude will hallucinate patterns from 3 deals.
Works with
ClaudeChatGPTGemini
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