How to build a world-class win-loss program from scratch

Introduction

Many organizations want to understand why they’re winning and losing sales opportunities—but they don’t have a systemic approach to do so. If that’s the case for your organization, you’re ready to start a win-loss or churn analysis program.

This guide focuses on how to collect feedback from new business (win/loss) opportunities and existing business (churn/stay) opportunities. The process of running a win-loss program versus a churn program is similar, with some nuance. By the end, you’ll have a comprehensive understanding of how to run your win-loss program and a better idea of the work involved in setting up and running it.

Gain internal buy-in

An important first step is gaining internal buy-in from the appropriate teams and stakeholders. It’s most important to get buy-in from the leadership team, sales organization, and sales/revenue operations team. The most reliable way to do this is to demonstrate the value of win-loss analysis by:

• ​Conducting 1–2 interviews
• ​Showing key stakeholders the insights collected
• ​Building a business case that shows clear ROI from running a win-loss/churn program

Leadership

Boards and executive teams with access to accurate, real-time win-loss data make more informed decisions, act more quickly, and with more confidence. Win-loss programs sponsored by the C-suite are more likely to receive funding, drive change across departments, and achieve meaningful ROI. If you can’t get buy-in from every leader, prioritize product, sales, marketing, and your CEO.

Sales

Getting buy-in from your sales team can make or break your program. The sales team maintains buyer relationships and may have veto power over which opportunities you can reach out to. Secure support from sales leadership and as many individual sales reps as possible.

• ​Involve sales leadership early on and make them feel ownership of the program.
• ​Allow them to help build the question set and have a say in outcomes.
• ​Find a respected sales rep and ask to interview a few of their recent opportunities to get them excited about the feedback.

Sales Ops

Get buy-in from your sales/revenue operations team. They’re often the gatekeeper for buyer contacts, and access is critical for getting enough feedback. You’ll also need CRM access to create a consistent, automated cadence for outreach and scheduling interviews.

Determine who to collect feedback from

The most important outcome from your win-loss analysis program is understanding where you’re losing, so you can improve your win rate within specific segments. Determine who you need to interview based on your business needs. For example, if you have a high churn rate, focus on existing business. If your win rate on new business is suffering, focus on segments like pipeline bands, competitors, or regions. Target the segment where you need the most insight.

Create an interview guide

While choosing contacts to invite, create your interview guide—a set of questions you can ask during interviews. The specific questions will vary depending on who you're interviewing (e.g., new business vs. existing business may need separate guides). Think of your guide as a set of possible questions, not a strict script. It should be extensive and exhaustive, but not every question will be asked in every interview. Common topics include “overview and origination,” “sales process experience,” and “product offering.”

Schedule your win-loss interviews

This part can be frustrating if not done correctly. Buyers are more likely to agree to interviews than surveys, but participation rates are key to success. Here are some tips:

Offer incentives

Offering an incentive, like a gift card, shows appreciation and boosts participation rates.

Use an email service

Use an email service for outreach, especially if integrating with your CRM, rather than sending emails one-by-one.

Use a scheduling service

Make it easy for buyers to participate. Use scheduling services like Calendly, Zoom Scheduler, or HubSpot to avoid back-and-forth emails.

Be persistent—while maintaining professionalism

Don’t be afraid to send multiple reminders. Professional persistence is key. Typically, 1–5 reminders are recommended.

Send an introduction email

Have someone the buyer knows—ideally their sales rep or a senior leader—send an introductory email. This increases participation by alleviating concerns about legitimacy. Highlight that your organization is running a win-loss analysis program, how insights will be used, and who will be reaching out to schedule the interview.

Track participant history

Track who has agreed to interviews, opted out, bounced, or been interviewed previously. This ensures you’re not reaching out to buyers who should be off-limits. Use an email service or a spreadsheet for tracking.

Conduct your win-loss interviews

With your guide ready and interviews scheduled, it’s time to conduct interviews. There’s debate on methodology:

1. 1.Ask every question as a script.
2. 2.Conduct a dynamic, adaptive interview using the guide as a reference.

Clozd recommends dynamic, adaptive interviews to uncover insights with flexibility.

Record, transcribe, and clean/edit the interview

Take basic notes, but focus on the conversation. Record and transcribe the interview for accuracy. Options for transcription:

1. 1.Do it yourself (high quality, time-consuming)
2. 2.Hire a human transcription company (high quality, fast, expensive)
3. 3.Use an automated transcription service (lower quality, inexpensive, instant)

Ensure the service protects privacy and confidentiality.

Summarize the interview

Highlight key takeaways, focusing on why the buyer made their decision, including strengths and weaknesses. Tag themes (e.g., sales process, product offering) and common words (e.g., competitor names) for tracking and analysis.

Analyze the feedback

After conducting, transcribing, and tagging several interviews, begin analysis:

1. 1.Analyze individual interviews.
2. 2.Analyze feedback across all interviews.

Don’t jump to conclusions from just one or two data points. Collect enough data to see trends before making changes. Tag themes in each interview to aggregate and identify strengths and weaknesses. Conduct at least 20 interviews within a segment before drawing conclusions. Use software or organized storage (like Google Drive or Dropbox) to keep track of findings.

Present your findings

Once you’ve collected and analyzed enough data, present your findings to stakeholders (leadership, sales, sales ops, etc.). Review findings together and determine which changes will have the most impact on your win rate. Identify clear action items as outcomes.

Working with Clozd simplifies this process

Clozd can take much of the work off your plate by running your win-loss program for you, allowing you to focus on enacting change.

You

• ​Gain internal buy-in (with Clozd’s help and resources)
• ​Deliver a list of buyer contacts for interviews (Clozd makes CRM integration seamless)
• ​Shape the interview guide based on your specific questions (Clozd provides a template)
• ​Use win-loss insights to create strategy and enact change (Clozd helps present findings)

Clozd

• ​Schedules all interviews (built into the Clozd Platform)
• ​Conducts every interview and summarizes findings
• ​Manages incentives for participants
• ​Deploys tactics to ensure higher participation rates
• ​Utilizes different feedback channels depending on segment
• ​Transcribes interviews and provides easy access to recordings
• ​Aggregates findings across all interviews and channels
• ​Creates and presents reports to any team at your organization
• ​Helps you win more