Pay-As-You-Go Win-Loss Interviews & Analysis

Experience affordable, high quality win-loss interviews with pay-as-you-go pricing. Quick and easy setup – with no CRM integrations required. 

Win-loss

Who is Win-Loss For?

A win-loss program is usually started at the request of a Chief Marketing Officer (CMO), who wants to deeply understand their companies win-rates so they can present this information to their leadership team, board of directors, and investors.

A win-loss program gives the deepest level of detail out of any feedback method. Data in the company’s CRM may be inaccurate, biased, incomplete, or lacking detail. This is often referred to as “dirty” CRM data. Likewise, surveys lack the depth of a win-loss interview.

A typical company looking to start a win-loss program has…

100+ employees and/or a large sales team

20+ closed won/lost deals per month

Expensive software or services ($50k+)

What is a win-loss interview?

A win-loss interview is a 30 minute conversation with a buyer who recently evaluated the company. Topics covered include the motivation behind the evaluation, the decision, product feedback, sales experience feedback, price comparisons, competitors considered, and future opportunities.

The conversation is recorded in Zoom and then transcribed and analyzed for key themes. WON uses a leading commercial software for coding, called Dovetail (ISO 27001 certified). The process is the same as what’s used for social science research.

Once 10+ interviews are conducted, companies can do an analysis, identifying themes.

What can you learn from individual win-loss interviews?

Feedback from an individual interview answers why that specific deal was won or lost. A CRM often only allows one field for the reason, we’ve found that there are many factors that contribute to a decision.

Sellers are often judged based on the outcome of the deal. (This is “resulting” or outcome bias.) Our research shows that buyers will purchase software, despite a negative sales experience, if the software meets their needs or the price is appealing. And even if the sales experience is “the best ever,” a buyer may choose to go with a different product for reasons ranging from contract to price to technical support.

A win-loss interview with a third party interviewer gives objective feedback to the sellers. Feedback is crucial when perfecting your craft. (Without it, sellers are left guessing!)

"We had have a low win rate. But there was a lot of uncertainty about why we were losing a lot of deals. There was a lot that were in final stage proposal and then they went in another direction and what happened?"


"The assumption is that they're not really giving our sales teams the candid reasons around winning or losing. The typical answers is there's no budget or price and those are always cop out answers for many. And C Suite was under the impression that there has to be other reasons outside of that."

What can you learn by analyzing a batch of interviews?

Beyond understanding the reasons why a company is winning or losing deals, a win-loss readout provides insights to multiple departments.

Win-Loss helps with:
  • Understanding key differentiators in comparison with competitors
  • Understanding the competitive landscape and who a company is losing to
  • Evaluating the effectiveness of the sales process and individual sellers
  • Understanding the strengths and weaknesses of the product or service
  • Understanding the strengths and weaknesses of major competitors
  • Evaluating the effectiveness of onboarding, implementation, and training
  • Discovering future opportunities and risks

These insights help companies:

  • Adjust messaging
  • Plan the product roadmap
  • Prioritize which product issues to fix
  • Identify future opportunities, potential case studies, upsell opportunities, and churn risks
  • Identify which sellers need training and support
  • Identify which sellers to celebrate and promote
  • Prioritize which content to create
  • Adjust pricing and packaging
  • Evaluate the company’s fit with specific verticals or segments

"This type of interaction feedback is something that differentiates us from our competitors even further because our competitors aren't doing this type of analysis today. So just learning from that is our ultimate goal."

"We were trying to get long term maximal strategic feedback as well in terms of what is the interest coming from? What are the new markets? What exactly is the prospect who's coming into what expecting from us?"

How does WON do Win-Loss Analysis?

Beyond understanding the reasons why a company is winning or losing deals, a win-loss readout provides insights to multiple departments.

A win-loss analysis (also called a “readout”) is delivered as a custom slide deck that’s 30-100 slides in length. WON’s analysis decks include a mix of trend charts, quotes, key insights, recommendations, and even video reels! 

Parts of the deck are presented to leadership teams, sales, marketing, product, compete teams, or other departments like customer success. Only a handful of slides are presented, while the rest of the research is available for those who prefer to dig deep into the data.

"I did about four readouts to four different teams and each one of them took away something different. So we met with product, sales, marketing, some EAM or asset management folks. So overall, very well, very impressed."

"Your readout texts are like insanely well crafted to the point where my job is stupidly easy right now. Like I just need to put in like some slides which are my findings and like the it blends in seamlessly well"

Sales learns how to improve their process. Marketing learns the messaging that resonates. Product learns what features customers care about. And Client Success teams learn what’s most important to their customers, and how to prevent churn. Win-Loss interviews work.

Why would our buyers agree to a 30 minute interview?

Buyers are compensated with a gift card or donation to a charity of their choice in exchange for their time. 

We suggest offering your prospect’s hourly rate for a 30 minute interview. So if a buyer earns $100 per hour, the gift or donation would be $100 for 30 minutes.

 

When should a company start a win-loss program?

The time may be right for your company to start a program, or outsource your in-house program, if you have 20+ closed deals a month and are looking for an analysis to understand why you’re winning or losing deals.

How does the process work?

1

 

You identify which accounts to invite to a win-loss interview.

2

 

You send an automated initial invitation by email, introducing WON. We’ll supply the email copy and a booking link, so your buyers can book their preferred time.

3

 

We’ll conduct the interviews, send thank you gifts, code the interview, and send you a reports and video recordings. Reports include a highlighted transcript.

4

 

Once we have 10+ interviews, you may request an analysis at any time.

Both interviews and analysis are pay-as-you go.
Please see our win-loss pricing.

Why do companies choose to work with WON?

Great question! When we ask our own buyers why they choose to continue working with WON, here’s what they say:

Pay-as-you-go pricing

WON offers a pay-as-you-go pricing model, with no minimums or monthly fees. This helps our clients prove the value of win-loss before commiting to a larger program.

No Contract

We don’t require contracts. Just pay for the interviews you need, when you need them.

Easy implementation

With our easy onboarding, clients can launch a win-loss program quickly. (Our record is 4 days from the signing of the SOW to the first interview!) Since CRM integration is NOT required, we are able to avoid lengthy procurement processes and serve clients with tighter security requirements.

Dovetail + AI Analysis

We use Dovetail as our research hub, allowing us to tag, analyze, and interpret interviews efficiently. With Ask Dovetail, AI delivers instant summaries, filtered searches, and evidence-backed insights, making data-driven decisions faster and easier.

"Insanely useful" readouts

Our goal is to deliver the best readouts in the industry, customized for every company's specific needs with video reels, buyer quotes, data visualizations, AI summaries, and recommendations.

Quality interviews

Our team has conducted hundreds of interviews across SaaS industries, including MarTech, GovTech, Compliance, Education, and Cybersecurity. 100% of our clients cite the quality of our interviews as a key reason for staying with us.

Responsive Service

You’ll have direct access to your lead researcher, who is your single point of contact. They will interview, code, build your deck, and answer your questions. Our team is responsive, friendly, and proactive! As a small company, we truly value every client.

Full Ownership of Your Interviews

You have full ownership of your interviews. We can set up and manage a Dovetail account for you can use your own instance. If you ever decide to end your win-loss program, you can download and retain all interviews and insights.

"I think you guys are doing a terrific job. Like you guys are immensely open to feedback. The way you pull out the insights for us, like insanely useful. I genuinly have good feedback. All I can do is give to us. It's been, it's tremendously fun working with you lot. Like seeing the kind of feedback coming in and trying to see like how exactly we can structure the investment. It's fun."

"I've run four or five of these win-loss programs over the last few years. And this has been the one that's provided the most actual definable value for us. And that's been that's been very, very positive and quite frankly all those other providers contact me on a monthly basis. I'm, no, I'm not interested. you can't match up what I'm getting here for the dollars that I'm spending."

We do one thing – and only one thing: Win-Loss programs.

So when you work with us, you’ll know you’re working with professionals who love delivering actionable insights that help you win.

I’m ready to get started! What’s the next step?

Fantastic! Book a time here to meet with one of our researchers. They’ll show you a sample analysis deck and answer your questions.

After this, we’ll sign a standard NDA and work order form, learn about your product, and get started! We do not require integration into your tech stack, so we’re often interviewing within two weeks of signing the contract.

At WON, we make it easy to get started with win-loss. Our resources are ungated – please check out our script, sample notes, and pricing.

 

 

Getting Started is Easy!

30 Minute Consultation

We’ll discuss your goals for your Win-Loss program, and answer any questions you have.

Thorough Onboarding

Once you’re ready to go, we’ll do a deep dive on your offerings, and customize your reporting.

First Interviews

We are ready to start conducting interviews and share results immediately.

Hear From Some of Our Clients

"We receive immense value from the Win-Loss interviews conducted by WON - our sales, marketing, product, and CS teams are all excited by the insights. The level of professionalism is very high, and the ease of working with the team at WON makes it a joy. I'm a fan!"

"You're gonna get good interviewers and you're gonna get good results and you're gonna get the money the value for your money."



Ready to get started?

Send us a note below, and we’ll connect with you right away.