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B2B Breakups: 200+ Interviews With The Ones That Got Away

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Never waste an opportunity to learn from a lost deal.

While each win-loss analysis is unique, over the years, we’ve found many common themes that keep costing B2B tech companies customers and deals. From inflexible pricing, to misguided messaging, to bad sales strategy, we’ll talk you through some of the most common B2B blunders and how to avoid them.

These insights have been distilled from more than 200 recent interviews with B2B buyers, decision makers, influencers, and product/service evaluators.

Rigid Pricing Models 

We found that inflexibility in pricing models was a major deterrent for B2B tech buyers.

There isn’t a one-size-fits-all pricing model. Some buyers prefer CAPEX pricing models with large sums paid upfront and depreciation and amortization as favorable accounting practices down the road. However, most customers favor OPEX models born of the cloud and as-a-service offerings. Others want something in between. Even within these two models, there’s room for named user pricing, concurrent user pricing, and add-on module pricing.

Choice is key. One product manager told us, “We started with an investigation of a transactional price, and all the vendors were able to do that. But then we wanted to move away from that and get an all-you-can-eat model. That was a real challenge for some of the vendors.”

While you don’t want your pricing to be super complicated, you want enough flexibility to be able to have a pricing structure that matches customer needs and can win the deal.

Whose problem is this?

  • Pricing teams developing which pricing models to offer.
  • Marketing teams positioning the pricing models.
  • Sales reps when customers ask, “How much does this cost me today and tomorrow?”
  • Enterprise vendors caught between on-prem and cloud business models.
  • Start-ups and SaaS technology pure-plays with inflexible pricing models.

Key Lessons

Strategize how you can be flexible without being complex. Consider how different CAPEX and OPEX pricing models may complement corporate spending cycles. For instance, we found that offering quarterly pricing in addition to annual and monthly has tipped the scales on some deals.

Customers often switch vendors when a big contract is up for renewal. Take away that trigger by offering OPEX pricing options or an early renewal incentive. This is becoming commonplace even for on-prem offerings.

Research Remedies

Research buyer personas, customer satisfaction with your pricing models, and competitor pricing models to determine the options that would be most appealing to target customers.

All-Or-Nothing Attitude


Company leadership usually wants sales teams to pitch the suite or even the entire platform to customers. This is often much more than B2B buyers want.

In our research, we heard many complaints about upselling or being forced to buy more than was needed. “I feel like you’re always in a sales environment where they’re trying to sell you their next solution even though you haven’t figured out how to use what you have,” one B2B buyer told us.

All-in-one is an appealing concept, but many customers are cautious whether such a pitch is too good to be true. Concerns are raised about integration, customization needs, lock-in, and lower adoption due to the replacement of favored tools.

A platform that does too many things at once can scare buyers away if they aren’t ready for the seismic shift of ripping and replacing critical systems.

Buyers also get annoyed when they sense that sales reps are more concerned with making another sale than they are with making sure the customer gets the solution they need. This ruins all possibility of strengthening the relationship with the buyer.

“As soon as you get on the phone with these guys, they’re ready to upsell you,” another customer complained to us. “They’re ready to [say], ‘Well if you get this tier, you can get this. If you get this tier, you can get this’…[But], I really wanted something specifically tailored to do what I want to do.”

Vendors should make sure they have offerings that match buyers’ requirements, not just expensively exceed them. Don’t let short-term goals cloud long-term strategy. Being pushy about closing this deal, now can cost you lasting relationships with buyers.

Whose problem is this?

  • Sales leadership when setting sales strategy.
  • Sellers when pushed to “sell the suite” to the detriment of lasting customer relationships.
  • Product leaders needing to build solutions that can be used piecemeal when necessary.
  • Marketers failing or neglecting to show how each piece works independently of the other.
  • Marketing teams determining the minimum SKUs.

Key Lessons

Recognize that some customers simply don’t need everything you have to offer right now. Have offerings that let customers bite off what they can comfortably chew.

Our research indicates that land-and-expand models tend to win more deals than pushing a top-down sale from the get-go.

Technology buyers increasingly want partnerships instead of transactional relationships. Our research indicates that vendors who prioritize land-and-expands sales are getting more wins than those that are driving for all-in-one.

Research Remedies

Researching key buying criteria, buyer personas, and go-to-market strategies can uncover how sales and marketing can best speak to buyers’ specific use cases and how product teams can build solutions that can accomplish customers’ “jobs to be done.”

Sales Not Doing Their Homework

B2B buyers notice when sellers are not up-to-speed on their company and use case. Customers can easily spot a canned demo, especially when requirements have been shared via RFP or similar.

If a sales rep doesn’t do their homework on target buyers, there are many tells. To name a few examples: a noticeable lack of the buyer’s industry context, not knowing customers’ “jobs to be done,” or offers that wildly miss the mark of buyers’ needs.

For instance, a marketing manager told us about sitting through a sales pitch where the seller clearly should have realized that the pricing model they were offering wasn’t feasible. “My total marketing budget is only about $700,000. For everything. That’s all my mailings, all my postage, all my creative, all my digital. So, obviously, a 50 or 80 thousand dollar spend just doesn’t make sense,” the marketer told us.

Another word of caution: sales reps, don’t assume your product or service is superior to the competition. You have to listen to your customers to know how they are evaluating potential solutions. Humility and curiosity about the customer’s needs are sure-fire methods for shedding the superiority complex.

Whose problem is this?

  • The C-suite when setting sales goals. Focus on long-term relationships not just end-of-the-quarter deal-closing.
  • Sales leadership hiring sales talent and setting best practices for engaging with customers.
  • Sellers during client conversations and initial engagements.

Key Lessons:

Sales needs to do their homework on buyers’ particular use cases and specific business contexts. Prepare for the sales pitch and listen to what customers say throughout.

Research Remedies:

Post-pitch follow-up calls and questionnaires gather important feedback from customers who said “yes” and those who said “no.” Win/loss market research studies uncover candid customer perspectives on sales performances.

Ignoring the Customer’s Existing Environment

B2B purchases don’t happen in a vacuum. Except in an unusual extreme overhaul, each new B2B purchase will have to interact with the products and services the buyer is already using. Hence, “How well will this solution play with our existing environment?” is an inevitable question in the B2B buyer’s journey.

In the words of a CIO we interviewed, “We can’t get past that roadblock. In our minds, it was like, ‘We can’t get to how it’s going to integrate with our system because you can’t demonstrate you can do it.’”

Of course, it’s not always obvious how a new product or service will fit in with existing solutions. In these cases, buyers need to know how much customization and configuration is in their future.

Product managers, remember that customers shy away from solutions that require months of coding, specialists, and other customization hoops. Whenever possible, buyers favor integration that can be accomplished with configuration rather than development.

Also, product managers, make sure integrations won’t break every time a vendor rolls out an update.

Marketers, avoid messaging that says the product can do anything for everyone. Instead, demonstrate how the solution can be used within the context of what particular customers are trying to accomplish. Targeted marketing and customer referrals are helpful here.

Sales, promising there will be no integration headaches is usually disingenuous. Just because you sell it doesn’t mean the customer won’t bail when implementation turns into an unexpected disaster.

Whose Problem Is This?

  • Product managers when prioritizing the goals and attributes for a new product or service.
  • Marketers when crafting messaging about use cases.
  • Sellers when explaining to the buyer what customizations and integrations they should anticipate.

Key Lessons:

Don’t overpromise seamless integration for everybody. Set accurate expectations for customization and integration in the buyer’s specific context.

Strive to make customization a process of configuration. Avoid code-heavy methods of customization. (Unless your target persona is a developer, in which case, go nuts!)

Research Remedies:

Key buying criteria and buyer’s journey research can determine how heavily customers are weighing configuration capabilities in their buying decisions.

Messaging Is Speaking The Wrong Language

Messaging that focuses on the technical aspects of a product when targeting business users is a common B2B misstep. This leads to poor awareness of the product’s business capabilities and may influence the buyer to believe the product is too complex for their case.

A business process improvement specialist shared their frustrations about sellers assuming that business users are also IT experts. “The business user pops in there and says, “Wait a minute, this feels like that IT mumbo jumbo that IT typically speaks at us. That makes no sense to us and we just shut down,” they said.

The same problem can appear when marketing overemphasizes the business angle when they should be targeting IT buyers.

Whose Problem Is This?

  • Sellers during sales pitches.
  • All facets of marketing.
  • Marketers tasked with lead gen especially.
  • Vendors entering a new market (vertical or solution-specific).

Key Lessons:

Talk to buyers in a language they’ll understand.

Research Remedies:

Messaging and positioning testing, buyer’s journey mapping, buyer persona, and go-to-market studies are specifically designed to inform customer targeting efforts. These research efforts explore all facets of the B2B buyer’s purchasing experience.

Star-Crossed Use Cases

Sometimes it’s just not a great fit.

Ideally, your sales team spends their time pitching to buyers whose needs match the solution’s key features and core competency. But that isn’t always the case.

Yes, it can be hard to retreat after investing time and effort in a target buyer. However, it’s much smarter to leave a doomed deal and refocus your energies where they will be more successful.

As one IT manager told us, “The partner was really wanting to get into customizations and how we can make this work for our business. We were taking the approach of, ‘Well, we want this product to work for us in a way that it’s designed for [rather than] trying to make this product work for us by forcing [it] to use our processes.’”

It’s essential for sales to recognize a doomed deal early in the relationship with a potential customer. That way, sales can refocus on buyers that would benefit from the solution’s core competency and features. You know, deals they might actually win.

At the same time, don’t make the buyer feel ditched. Be honest that you’re not a fit, leave them in a good place, and re-engage with other products down the road that are more in the sweet spot.

Success comes from fitting the product to the customer, not the customer to the product or service.  

Whose Problem Is This?

  • Product teams during the design process. It’s best to design for specific “jobs to be done” rather than just shooting for the moon.
  • Sales when deciding which customers to prioritize. Devote the most time and effort to buyers that benefit from the product’s core competency.

Key Lessons

If you’re building a product for a particular buyer persona, make sure you have a firm grasp of their “jobs to be done” that need to be accomplished via your solution.

Target buyers that have a need that can be met by the core competencies of your product or service.

Research Remedies

Customer journey mapping, key buying criteria and market opportunity assessments uncover why buyers are looking for a product or service in the first place. This research determines the functionalities needed to accomplish buyers’ “jobs to be done” along with the features that customers prioritize the most.

Turn Loss Into A Strategic Gain

Each lost deal, when properly analyzed, yields useful information to hone your product, sales, and marketing strategies.

It all boils down to understanding buyers’ wants and, more importantly, their needs. This insight gives you the ability to:

  • Determine which customers to target.
  • Strategize ways to expand existing customer accounts and form lasting relationships with new customers.
  • Build products that satisfy buyers’ “jobs to be done.”
  • Create solutions that don’t give and charge buyers way more than they need or want.
  • Use messaging that speaks to buyers in terms they understand.
  • Offer pricing model options that will appeal to target customers.
  • Recognize use cases that aren’t a good fit and devote sales efforts elsewhere.

Want to turn your lost deal into an insight gain? Get in touch.

Research for this analysis was conducted by Jacob Dittmer, Tyler Honsinger, and Scott Swigart. Learn more about our research for B2B technology companies.

Sales Needs A Say In Strategy

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Your sales team is conducting qualitative research all the time. Talking to them is perhaps the lowest cost qualitative research project you could possibly do. It’s also your best chance to achieve a strong sales strategy in sync with the goals of your organization.

This article is based off a B2B Revealed episode.

You can listen to the episode or read the article below.

B2B Revealed – ON: iTunes, Stitcher, and Google Play

Unfortunately, many companies undervalue their sales professionals. This results in scores of missed opportunities and the alienation of the sales team.

Companies often make two big mistakes:

  1. Companies’ market research teams typically don’t have a great perception of their own sales team.
  2. Sales teams aren’t often invited to participate as major stakeholders in market research studies.

Having worked with many Fortune 1000 clients, I’ve seen this happen a lot. I know who gets invited to the table. Usually, representatives from marketing and product development are invited right away. If the project is important enough, a vice president or C-level executive gets an invite too. Sales leadership is skipped over far too often. That is a huge mistake.

Sellers and market researchers typically have very different personalities.

Sales and market research demand very different approaches to be effective at each job. 

Think about how each role would behave in a meeting to discuss a research project. You’re probably picturing the following:

  • The salesperson will talk a lot and the market researcher will ask a lot of questions.
  • The salesperson will push the group to make a decision and the market researcher will counsel patience.
  • The market researcher will rely on data and the salesperson will rely on instinct.

Frankly, there may be an element of truth to these stereotypes. No problem.

Different perspectives are not a bad thing. The whole room will be pushed to consider possibilities they wouldn’t have otherwise.

I’ll give an example of the sales-as-an-afterthought syndrome. On a recent project for a Fortune 200 company, we received a list of stakeholders as the project kicked off. Since this project was large, the stakeholder list was understandably large as well. There were 15 names from all over the business. Product development, the executive team, marketing and, of course, market research team leads, were all represented. Oddly, not a single salesperson, sales manager, director of sales or even a sales VP were on the list.

To make matters worse, this was a project to figure out which opportunities the client should pursue in a market crowded with competitors. It’s hard to imagine that sales leadership wouldn’t have something worthwhile to contribute to the subject of sales strategy. They may have already had the answers to some of the questions that the researchers were after. At the very least, sales leaders undoubtedly had highly relevant questions on the topic and should have been given the opportunity to ask. Further, the outcome of the study was directly pertinent to crafting an effective sales strategy. It made zero sense to have no one to represent sales on the stakeholder list.

There is a false perception that products sell themselves.

This is another big reason why I think invites to sales leaders get “lost in the mail.”

You see this bias crop up in many Silicon Valley companies. They might say, “We don’t worry about what the competition is doing. We just build great products.” They may proudly boast of their focus on “doing” over selling.

I’ve even seen companies advertise that they don’t have salespeople. They do, but they make up a title like “customer success representative” to call them instead. I don’t buy it.

I guarantee you that every company has someone (or several someones) in sales even if they don’t title them like they are.

I’m sorry, products don’t just sell themselves. Someone has to tell the narrative that connects the product to a set of business problems or opportunities.  Someone has to develop and execute on a sales strategy.

Regrettably, judging from the overwhelming majority of stakeholder lists for studies, it looks as though many-a-market research project completely overlooks this fundamental truth.

The experience of sales leaders is unduly discounted as a valuable source of qualitative data.

The biggest reason why sales teams are not invited to the stakeholder team is that people tend to think that the data salespeople can provide is inherently biased. 

ALL data is inherently biased.

Download numbers, SaaS service trial counts, website page visits, feature usage, NPS scores… All that data has an agenda too. It’s collected for a specific purpose and intended to measure a specific thing. It doesn’t necessarily bring context along with it. (That’s what market researchers are for.)

In many ways, B2B salespeople are conducting qualitative research every single day that they work for your company.

Your first reaction to this statement may be, “No way. They don’t record the conversations they have. They don’t transcribe them. They certainly don’t code the responses, and they don’t build findings decks.” You’re right. They don’t.

They do have conversations with real and potential customers every single day. With each interaction, salespeople use their personal experience to influence the behavior of buyers. That makes their personal experience an incredibly important factor for sales strategy.

Conversations between salespeople and buyers drive:

  • Customer engagement.
  • Future conversations with potential customers.
  • The actual sales of your company’s product.

B2B sales cycles last months or even years. Sellers engage with a buying team of roughly 5-10 people through what might amount to tens or even hundreds of online, phone, and in-person interactions.

Basically, your sales team has a ton of untapped data on your customers and potential customers.

Each B2B sale is a mini qualitative research project.

What are some ways you can engage with sales to mine this kind of intelligence? How can you infuse your next research effort with sales insights? How can you learn more about your company’s sales strategy? Ask your sales team these three questions.

Can I see a demo?

You haven’t properly researched the product unless you’ve seen it demonstrated.

With B2C software solutions and products, this is usually an easy process. You can go down to the mall and see or buy the product, or read public reviews.

With B2B solutions, it’s different. These products cost tens or hundreds of thousands of dollars, so you can’t just buy them yourself.

For some solutions, like technology products in B2B, you can’t be expected to fully understand the product unless you’re trained on it. Just like the people who are going to use this solution, you can’t be expected to just pick it up and run with it. A demo is the easiest way to get up to speed on a complex product. Simply ask for one.

Salespeople demo the product for real customers every single day. Asking for an hour of their time is a small price to pay to conduct effective research on the product or solution and its competitors.

Who do you sell to and who do you avoid?

So often, market research targets personas that have been in play for so long that they are no longer questioned.

The sales team knows what’s really working. They know the personas who bite and the personas who don’t.

Ask them who they go for first at the start of a sales cycle by:

  • Role.
  • Title.
  • Type of company.

This will tell you at least one of the buyer personas you need to target in your research efforts.

Then ask them the same questions about the big sales. The ones that take longer and require more effort but would provide more long-term benefits. You’ll surface additional buyer personas or even whole market segments that need to be considered.

Make sure to also ask the crucial question of who they never try to sell to by role, title and type of organization. You’ll get a sense of which customers are actively buying competing solutions or aren’t buying any solutions.

Pitch Me

The third thing you want to do is ask your sales team to share their pitch.

In complex B2B sales, there’s no script that a seller reads. It’s not a standardized process.

Your best salespeople hone their pitch using the positive and negative feedback they receive from talking to prospective and current customers. If they highlight certain features, you can guarantee there’s a data-driven reason for that. If they talk up pricing in a certain way, there’s a data-driven reason for that too. If they specifically comment on competitors, there is a reason why.

Inviting sales to the stakeholder team should be common practice.  It’s in your company’s best interest to make it mandatory. You’re guaranteed to get insights that will help shape your study in positive ways. You’re also likely to make all the other stakeholders in marketing, product development, and executive teams happier with the results. Not mention sharpen your sales strategy.

This podcast is brought to you by Cascade Insights. We specialize in market research and competitive intelligence for B2B technology companies. Our focus allows us to deliver detailed insights that generalist firms simply can’t match. Got a B2B tech sector question? We can help.