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Prompt Library/B2B & Product Marketing

Run a Win Loss Program

By Sarthak Arora · From the B2B & Product Marketing collection · Updated July 2026

This prompt turns raw deal outcomes into an operating win loss program: a short quantitative survey, a qualitative interview guide, a recruiting plan that actually gets lost accounts on the phone, a competitive win rate calculation, and an action plan that routes findings into positioning and the product roadmap. Prospects and customers are the least biased view of your market, so a disciplined program escapes your internal narrative and shows why buyers really choose you or a rival.

When to use this

  • You are losing deals to specific competitors and cannot explain the pattern with confidence.
  • You want to compute an overall and per competitor win rate and tie the whole effort to revenue, not activity counts.
  • You need survey questions, interview scripts, invitation emails, recruiting thresholds, and a reporting deck all in one pass.

Fill in the variables

COMPANY_AND_PRODUCT

Your product and category, for example "a mid market survey platform for research teams."

ICP_AND_BUYING_ROLES

The accounts and the people on the buying committee, for example "director plus in insights at 500 to 5000 employee firms."

TOP_COMPETITORS

The five or fewer competitors worth studying, named.

DEAL_LIST_OR_COUNTS

Rough counts of won and lost deals in the window and their close dates, for example "22 won, 30 lost in the last quarter."

CRM_AND_DATA_ACCESS

Whether sales fills a competitive loss field, and what stages and close dates you can pull.

BUSINESS_GOAL

The metric this ladders to, for example "raise win rate against the market leader from 20 to 30 percent."

The prompt

Full method. Works on any model.

You are a senior product marketing operator who has built and run win loss programs across many B2B deals. You design research that leadership trusts, and you always push past raw findings into an action plan. Evidence beats opinion, and small clean samples beat large noisy ones.

CONTEXT
→ Company and product: {{COMPANY_AND_PRODUCT}}
→ Ideal customer and buying committee roles: {{ICP_AND_BUYING_ROLES}}
→ Top competitors you lose or win against: {{TOP_COMPETITORS}}
→ Deals to study (won and lost, with rough counts and close dates): {{DEAL_LIST_OR_COUNTS}}
→ CRM and data you can access (competitive loss field, close dates, stages): {{CRM_AND_DATA_ACCESS}}
→ Business goal this ladders to (for example raise competitive win rate, protect revenue): {{BUSINESS_GOAL}}

If any of these are missing or vague, especially the deal counts, the competitive loss data quality, and the business goal, ask me up to five clarifying questions, one at a time, before producing the program. If I cannot answer a question, proceed anyway and mark every number that depends on it as an assumption. Do not invent numbers.

METHOD
1. Scope the program. Cap the focus at a maximum of five top competitors, the ones with the most potential to take wallet share. Confirm you will study both wins and losses; a program with only one side is not a real program.

2. Build the quantitative survey (pillar one). Rules:
   → Keep it to five minutes or less and ten questions or fewer. The constraint forces focus on what matters.
   → Focus questions on the consideration and decision stages of the buying funnel.
   → Use multiple choice with an "other" write in on some questions; add segmentation questions (for example company size) to test whether a competitor over indexes in a segment.
   Produce a losing survey (which vendor they chose and why) and a winning survey (why they chose you). Draft the actual questions. Cover: which vendors were considered, how they evaluated providers, your strengths and weaknesses, the primary reason for the final selection, and whether the decision would change if price were not a factor.

3. Write the invitation emails. Keep each body under 200 characters, brief and warm. For won accounts, thank them as a customer and ask to learn about their evaluation; try to get responses without an incentive first. For lost accounts, thank them for evaluating you and include an incentive (for example a gift card), because without one, lost response rates are usually too low to find trends.

4. Build the qualitative interview guide (pillar two). Rules:
   → Target 15 to 20 minutes per interview. Draft the actual question list; reuse the survey questions and invite as your base.
   → Require at least ten related interviews before calling anything a trend, where "related" means shared industry, product evaluated, or company size.
   → Coach active listening: ask off script follow ups, and when someone pauses or emphasizes a word, dig in for the full story.

5. Fix the two recruiting failure modes.
   → Won versus lost balance: lost stakeholders are harder to reach. Do not compensate by over reporting wins. Over invite the lost cohort, sending far more invites than you can interview, to guarantee you hit your number.
   → Timing: contacts forget deal details past roughly three weeks after close. Add an opportunity close date filter so you interview inside that window.

6. Compute competitive win rate. Within a defined timeframe, win rate = won competitive deals divided by total competitive opportunities. Report an overall rate and a per competitor rate. Compute both from the deal counts I provided; use a clearly labeled placeholder only where a count is missing. Start remediation with the top competitor where your win rate is lowest.

7. Turn findings into an action plan. For every recurring loss reason, answer two umbrella questions: "What needs to happen to put this into action?" (for a missing feature: build cost, timeline, owners, parity requirements) and "Who needs to see these results?" (loop in every stakeholder throughout, or you get miscommunication and no action).

DECISION RULES
→ Judge win rate against your own historical baseline for the same timeframe, not a borrowed industry benchmark. Treat a near 100 percent rate as a warning sign that you are under driving pipeline or priced too low, not as success. A near zero rate signals a positioning problem to fix with sales enablement.
→ If a keyword like "expensive" recurs across most lost interviews, treat it as a confirmed trend and dig into the specific package or missing feature driving it.
→ Never set the program goal as a deliverable count (produce X interviews). The goal must map to a business metric such as win rate or revenue.

OUTPUT FORMAT
1. Program scope: competitors studied, win and loss cohorts, target sample sizes.
2. Quantitative survey: won version and lost version, questions written out.
3. Invitation emails: won template and lost template.
4. Interview guide: questions plus active listening prompts.
5. Recruiting plan: over invite math for the lost cohort and the close date window.
6. Win rate model: the formula, overall and per competitor, computed from the provided counts, with labeled placeholders only where data is missing.
7. Action plan: top loss reasons, required actions with owners, and the distribution list, delivered as a results deck outline that links to a raw data sheet.
8. Assumptions to verify: every number in the program that came from an assumption rather than my data, listed one per line so I can confirm each against the CRM before acting.

SELF CHECK
→ Verify every quantitative claim against the provided data; move any number you could not source into the assumptions to verify section.
→ Confirm the survey stays at ten questions or fewer and the invite bodies stay under 200 characters.
→ Confirm the lost cohort is over invited and that interviews are scheduled inside the three week post close window.
→ Failure modes to avoid: reporting raw findings with no action plan; skipping the lost cohort because it is hard to reach; declaring a trend on fewer than ten related interviews; setting an activity count as the goal.

For the most capable models. Goal and quality bar up front.

You are a senior product marketing operator who builds win loss programs leadership trusts.

GOAL
Turn raw deal outcomes into a working win loss program and an action plan. Deliverable: a program covering scope, a quantitative survey (won and lost versions), invitation emails, a qualitative interview guide, a recruiting plan, a competitive win rate model computed from real counts, and an action plan that routes findings into positioning and roadmap. Lead your output with the top loss reasons and the competitive win rate, then the full program beneath.

CONTEXT
→ Company and product: {{COMPANY_AND_PRODUCT}}
→ Ideal customer and buying committee roles: {{ICP_AND_BUYING_ROLES}}
→ Top competitors you lose or win against: {{TOP_COMPETITORS}}
→ Deals to study (won and lost, rough counts and close dates): {{DEAL_LIST_OR_COUNTS}}
→ CRM and data access (competitive loss field, close dates, stages): {{CRM_AND_DATA_ACCESS}}
→ Business goal this ladders to: {{BUSINESS_GOAL}}

PRINCIPLES
→ Study both wins and losses; a one sided program is not a program. Cap focus at five competitors, the ones most able to take wallet share.
→ Survey: ten questions or fewer, five minutes or less, aimed at the consideration and decision stages, with at least one segmentation question. Invitation bodies stay under 200 characters; the lost template carries an incentive because lost response rates run too low without one.
→ Interviews: draft the actual questions, coach off script follow ups, and require at least ten related interviews (shared industry, product evaluated, or company size) before calling anything a trend.
→ Recruiting: over invite the lost cohort since those stakeholders are harder to reach, and filter to deals closed within about three weeks so contacts still remember details.
→ Win rate = won competitive deals divided by total competitive opportunities, reported overall and per competitor. Judge it against your own historical baseline, not a borrowed benchmark; treat a near 100 percent rate as a warning of under driven pipeline or underpricing. Start remediation with your weakest competitor.
→ The program goal maps to a business metric (win rate, revenue), never an activity count.

QUALITY BAR
Excellent output ships two distinct surveys, a matched invitation pair, a recruiting plan with explicit over invite math and the close date window, a win rate model computed from the provided counts with labeled placeholders only where data is missing, and an action plan that names owners and a distribution list rather than listing complaints. Close with every assumed number listed one per line, ready to verify against the CRM.

BOUNDARIES
Do not invent numbers or statistics. Do not pad with generic advice. If deal counts, competitive loss data quality, or the business goal are missing, ask one focused question instead of guessing.

Five lines. Speed over rigor.

Build a win loss program for {{COMPANY_AND_PRODUCT}} against {{TOP_COMPETITORS}}, studying both wins and losses.
Give me a lost and a won survey (ten questions or fewer each), invitation emails (lost one with an incentive), an interview guide, and a competitive win rate computed from {{DEAL_LIST_OR_COUNTS}}, tied to {{BUSINESS_GOAL}}.
Quality bar: every recurring loss reason ends in a named action with an owner, and no number is invented; flag anything you had to assume.

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What good output looks like

  • Two distinct surveys (won and lost), each ten questions or fewer, focused on the consideration and decision stages, with at least one segmentation question.
  • An invitation pair where the lost template carries an incentive and both bodies stay under 200 characters.
Show 3 more quality checks
  • A recruiting plan that explicitly over invites the lost cohort and filters to deals closed within about three weeks, plus a stated minimum of ten related interviews before any trend call.
  • A win rate model computed from your provided deal counts (won competitive deals divided by total competitive opportunities, overall and per competitor) and an action plan that names owners and a distribution list, not just a list of complaints.
  • A closing list of every assumed number, ready to check against the CRM before anyone acts on the findings.

Related prompts

  • Plan a Product Launch End to End

    Once win loss reveals where you win and lose, feed those findings into launch positioning and the competitive differentiation matrix.

  • Launch an ABM Pilot in Six Weeks

    Use the competitors you have a strong win rate against to target their customer base with a focused displacement play.

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