Analyze · Win/Loss Analysis

Compare Win Rates Across ICP Segments

Slice your deal data by ICP segment to see where your win rate is real, where it's noise, and where to double down.

foundermanagerIntermediate2 hours
When to use
Use when you sell into multiple verticals or company-size bands and want to know where to focus next quarter's pipeline build. Best with 30+ closed deals across at least 3 segments.
The prompt
You are an analytics-minded sales leader for a digital marketing agency. You compute and compare segment-level win rates honestly, including statistical caveats when sample sizes are small.
Agency: [AGENCY_NAME] — [SERVICES] | Period: [PERIOD] | Segmentation: [SEGMENTATION_DIMENSION] (e.g., industry, company size band, service line, source) | Data:
[DEAL_LIST]
(For each deal: segment value, won/lost, ACV, sales cycle days.)
Compute win rate, average ACV, and average cycle per segment. Rank segments by win rate. Highlight: (1) the segment with the best blended profit signal (win rate x ACV), (2) any segment with a win rate notably below the agency average, (3) any segment that's too small to draw conclusions. Recommend where to lean in and where to deprioritize next quarter.

- Show the math for each segment (won / total = rate).
- Any segment with fewer than 5 total deals: mark as "directional — insufficient sample."
- Compare each segment's win rate to the overall agency win rate.
- Recommendations must follow from the data, not general best practice.

Output: (1) Segment table — Segment | Total deals | Won | Win rate | Avg ACV | Avg cycle. (2) Overall agency baseline. (3) 3 ranked recommendations (lean in / hold / deprioritize) with the segment(s) named and the reason.
Variables
  • [AGENCY_NAME] — Your agency name
  • [SERVICES] — Service lines covered
  • [PERIOD] — Date range analyzed
  • [SEGMENTATION_DIMENSION] — How you want to slice — industry, size band, service, source, etc.
  • [DEAL_LIST] — All closed deals (won + lost) with segment value, outcome, ACV, and cycle
Example input
Agency: Northstar Digital — SEO, Paid Search | Period: trailing 12 months | Segmentation: industry
Deals (summarized):
DTC: 12 total, 8 won, avg ACV $6.4k/mo, avg cycle 24d
B2B SaaS: 10 total, 2 won, avg ACV $7.8k/mo, avg cycle 47d
Local services: 6 total, 4 won, avg ACV $3.2k/mo, avg cycle 19d
B2B Manufacturing: 4 total, 1 won, avg ACV $9.5k/mo, avg cycle 58d
Example output
Segment table:
DTC — 12 deals, 8 won, 67% win rate, $6.4k ACV, 24d cycle.
Local services — 6 deals, 4 won, 67% win rate, $3.2k ACV, 19d cycle.
B2B SaaS — 10 deals, 2 won, 20% win rate, $7.8k ACV, 47d cycle.
B2B Manufacturing — 4 deals, 1 won, 25% win rate, $9.5k ACV, 58d cycle (directional — insufficient sample).

Overall agency baseline: 15 won / 32 total = 47% win rate.

Recommendations:
1. Lean in: DTC — well above baseline, healthy ACV, fast cycle. Best blended profit signal. Add 2 SDRs of capacity here.
2. Hold: Local services — high win rate but low ACV caps revenue impact. Keep as referral/inbound only.
3. Deprioritize: B2B SaaS — 27 points below baseline despite higher ACV. Pause outbound here for 1 quarter and reassess after fixing competitive gap.
Pro tips
  • Try slicing by lead source as a second pass — segment performance often hides a source-quality story.
  • Don't kill a segment after one bad quarter — confirm with 2 consecutive periods before pulling investment.
  • Win rate x ACV is the right ranking metric, not win rate alone — high win rate on $2k retainers won't fund the agency.
Works with
ClaudeChatGPTGemini
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