Analyze · Win/Loss Analysis

Build a Win/Loss Quarterly Summary

Roll up a quarter of win/loss findings into a 1-page executive summary your leadership team can act on in 10 minutes.

foundermanagerIntermediate2 hours
When to use
Use at the end of the quarter after running deeper analyses (segment win rates, loss reason clustering, competitive losses) and you need a leadership-ready 1-pager for the QBR or board update. Don't run it as the first pass.
The prompt
You are an analytics-minded sales leader for a digital marketing agency. You write executive summaries that are short, evidence-based, and end in clear decisions — not a wall of caveats.
Agency: [AGENCY_NAME] — [SERVICES] | Period: [PERIOD] | Inputs:
[ANALYSIS_INPUTS]
(Pre-run findings: headline metrics, top win/loss themes, segment win rates, top competitive losses, post-mortem highlights.)
Synthesize the inputs into a 1-page quarterly win/loss summary for leadership. Lead with the 3 things they need to know, then back them up with the evidence already in the inputs, then end with the 3 decisions or investments being recommended for next quarter.

- Stay under ~400 words.
- Every claim must trace back to the inputs — don't introduce new findings.
- Flag any pattern the underlying analysis marked as "directional / low sample."
- No rep-bashing. Recommendations should target process, ICP, or positioning, not individuals.

Output 4 sections: (1) Headline (3 bullets — what leadership needs to know). (2) Quarter at a glance (metric table: deals, win rate, avg ACV, top segment, top loss reason). (3) Themes (2 win themes + 2 loss themes with 1-line evidence each). (4) 3 recommended decisions for next quarter with rough investment level.
Variables
  • [AGENCY_NAME] — Your agency name
  • [SERVICES] — Service lines covered
  • [PERIOD] — Quarter being summarized
  • [ANALYSIS_INPUTS] — Pre-run findings: metrics, themes, segment win rates, competitor losses, post-mortems
Example input
Agency: Northstar Digital — SEO, Paid Search, Web | Period: Q1 2026
Inputs:
- Q1 metrics: 32 deals, 47% win rate, $6.8k/mo avg ACV.
- Top win theme: DTC SEO via referral, 67% win rate.
- Top loss theme: lost to AdVenture in Paid Search, $234k ACV at risk.
- Segment win rates: DTC 67%, B2B SaaS 20%, Local 67% (low ACV), B2B Mfg 25% (directional).
- Post-mortem: BrewHaus loss — slow attribution response + late multi-threading.
- Emerging play: New CMO Diagnostic (2 wins).
Example output
Headline: (1) Win rate held at 47% on 32 deals — stable but masked by segment swings. (2) Paid Search lost $234k to AdVenture across 3 deals — the biggest single drag this quarter. (3) DTC SEO via referral is our strongest motion at 67% win rate — and we're under-investing capacity here.

Quarter at a glance: 32 deals | 47% win | $6.8k avg ACV | top segment DTC SEO | top loss reason competitive loss to AdVenture.

Themes: Win — DTC referrals close fast (67%, sub-30-day cycles). Win — "New CMO Diagnostic" play produced 2 wins, ready to formalize. Loss — Paid Search reporting perception gap vs AdVenture (3 deals, $234k). Loss — B2B SaaS win rate at 20%, 27 points below baseline (10 deals, real signal).

Decisions for next quarter: (1) Invest: add 1 SDR focused on DTC referral activation (medium). (2) Fix: redesign PS reporting + live attribution demo before May renewals (low cost, high urgency). (3) Pause: B2B SaaS outbound for one quarter; reassess after competitive teardown (cost-neutral).
Pro tips
  • Write the headline last — once you've laid out the themes, the 3 things leadership needs to know become obvious.
  • Always include 1 thing that's working — leadership tunes out summaries that are 100% problems.
  • Tie each recommended decision to an investment level (cost-neutral / low / medium / high) so the conversation jumps straight to approval.
Works with
ClaudeChatGPTGemini
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