Win / Loss Analysis

Turn Insights Into Advantage

Uncover why deals are won or lost and strengthen your positioning, messaging, and GTM strategy with actionable recommendations.
win loss analysis

Who Is this For?

I help early-stage and scaling agentic AI / fintech platforms turn win/loss insights into stronger positioning, messaging, and sales effectiveness that wins the trust of risk-averse finance buyers (CFOs, Controllers, and finance teams).
 
Ideal for teams that want to reduce sales friction, improve win rates, and refine their go-to-market approach based on real deal outcomes rather than assumptions.

Project Details

This Win / Loss Analysis project delivers deep, actionable insights into why deals are won or lost, helping you strengthen your Agentic AI positioning, messaging, and sales effectiveness with finance buyers.
 
Identify patterns, fix hidden gaps, and build a more effective sales and marketing approach.

Project Includes:

  • Detailed analysis of recent closed-won and closed-lost deals
  • Identification of patterns, objections, and differentiation opportunities
  • Competitor comparison and positioning gap analysis
  • Actionable recommendations for messaging, sales process, and GTM improvements
  • Prioritized roadmap with quick wins and longer-term strategic changes

Basic Overview:

  • Win / Loss Deal Analysis
  • Sales Team Interviews & Insights
  • Marketing Strategy Report
  • Tailored Action Plan
  • Optional Strategy Call
  • Optional Slide-Deck

Price & Scope:

After purchasing the project, send requirements so I can start the project. Delivery time starts when I receive requirements from you.

Starter

$1,797

Basic Win/Loss Review:

High-level analysis of 8–10 deals with key patterns and recommendations.

  • Delivery Days:  10
  • Revisions:  1
Standard

$2,597

Full Win/Loss Analysis:

In-depth analysis of 15–20 deals with sales interviews and actionable insights.

  • Delivery Days:  14
  • Revisions:  2
Advanced

$3,597

Premium Win/Loss & Strategy:

Full analysis with interviews, strategic recommendations, and a 60-min workshop.

  • Delivery Days:  18
  • Revisions:  2

Frequently asked questions

You’ll receive a detailed win/loss analysis report with key insights from won and lost deals, identified patterns, and strategic recommendations to improve positioning, messaging, and win rates. Delivered in PDF and editable Google Docs.

  • Starter: 10 days (7 days with Fast Delivery)
  • Standard: 14 days (9 – 10 days with Fast Delivery)
  • Advanced: 18 days (12 – 13 days with Fast Delivery)

Each tier includes revision rounds. Additional revisions are available as an add-on. Revisions are typically completed within 24–48 hours.

Yes. The quality of the analysis depends heavily on the data and context you provide (won/lost deals, sales team access, current positioning, and goals). I’ll guide you with clear questions to get started.

Yes. Even early-stage companies can benefit from win/loss analysis, especially after running initial sales cycles or pilots. The project can be adapted based on the volume of deals available.

Steps for Completing the Project

Step 1:

After you purchase the project, you must send the following requirements listed below so I can start the project. Delivery time starts once I receive requirements from you.

PROJECT REQUIREMENTS:

Please give a clear description of your Agentic AI product/tool.

  • What does it do?
  • What are its key features and unique capabilities (e.g., autonomous agents, orchestration, tool use, memory)?

Please share a list of recent won and lost deals (ideally 15–25 opportunities).

Include basic details such as deal size, stage, outcome, and any available notes or CRM data.

Will your sales team be available for interviews? (Typically 30–45 minute conversations.)

Please let us know how many sales reps we can speak with.

Please share any existing positioning, messaging frameworks, battlecards, or sales materials you currently use.

What are your main goals for this win/loss analysis?

(For example: improve win rate, understand why deals are lost, refine positioning and messaging, support sales enablement, etc.)

 

Do you have a preferred timeline or any important deadlines for this project?

Please share any other relevant information (such as recent changes in the market, new competitors, or internal challenges) that could help guide the analysis.

 

Would you like us to also conduct interviews with won or lost customers?

(This is included in the Advanced tier or available as an add-on.)

Step 2:

I work on your project following the steps of the delivery process listed below. Revisions may occur after the delivery date.

PROJECT DELIVERY PROCESS:

I review your submitted information, won and lost deal data, and current positioning/messaging materials to understand the scope and goals of the analysis.

I analyze the provided won and lost deals to identify initial patterns, trends, and potential reasons behind wins and losses.

I conduct interviews with your sales team (and customers in the Advanced tier) to gather deeper qualitative insights behind the data.

 
 

I synthesize the findings into clear insights and develop strategic recommendations to improve positioning, messaging, and win rates.

You receive the initial win/loss analysis report and recommendations for review.

I incorporate your feedback based on the number of revision rounds included in your tier, with quick turnaround.

You receive the final polished report with all insights and recommendations in both PDF and editable formats (Google Docs), with full ownership.

A 60-minute strategy workshop is available as an optional add-on.

Step 3:

Upon final delivery, please perform the following steps listed below.

  1. Review the work
  2. Release payment
  3. Provide feedback.

Ready to Work Together?

I’d love to help you turn win/loss data into powerful insights that improve your Agentic AI positioning, messaging, and overall sales effectiveness.
SCHEDULE PROJECT