How to Fix the 7 Things People Hate About Buying Software

January 30, 2024
There are seven things that make buying software unpleasant, frustrating, and regrettable, but they're all things B2B teams can fix.
Sam Senior
Table of Contents

Back in 2020, I was shopping around the idea of the first version of TestBox: a marketplace that let B2B software buyers try multiple competing products side-by-side. 

My goal for TestBox was (and still is even though we've since pivoted to a SaaS product rather than a marketplace) to improve the B2B software buying experience.

Part of my research entailed talking to people who had recently purchased B2B software. I spoke with buyers at 50+ companies, and I heard the same complaints in every conversation.

A slide from TestBox's original pitch deck summarizing our research. 

There are seven key things that can make buying software incredibly unpleasant, frustrating, and — in many cases — regrettable.

The bad news: these issues have remained prevalent in the four years since I originally conducted my research. 

The good news: they're all things B2B sales teams can fix.

1. Buying software is complicated, distracting, and risky

It's no one's full-time job to buy software. 

Buyers' jobs are to analyze data, build brand awareness, support customers, write code, lead a team, etc. They might buy software once a year, once every few years, or once in a lifetime.  

They're not experts at buying software. They don't know what to look for, what to watch out for, or where to even start. They're afraid that making the wrong decision could put their jobs at risk. And they have other work they need to be doing.

We take these buyers with all of their reservations, fears, and distractions and pair them up with someone whose entire job is to sell software. It's understandable that they're wary.

How to fix it

To make buying easier for buyers, it's important to go out of your way to provide the information they need to feel confident that they're making the right decision. 

At TestBox, we've done this in a few ways:

  • We worked with a third-party consultant to write a buyer's guide to demo automation software — including a breakdown of the market and a list of questions to ask vendors — and published it on our website for all prospective buyers to read and use.
  • For one lead that became a customer, we created a four-page long document comparing TestBox side-by-side with a competitor the lead was also evaluating. It listed all of the buyer's criteria and explained how each criterion was handled by both tools. Most importantly, this was verified by both us and the buyer we were speaking with, and we were honest about where TestBox didn't have the best solution.
  • We've manually created ROI calculators for a number of leads to help them make their business cases for getting the budget to buy TestBox.
We built this ROI calculator for a lead that eventually became a customer. The numbers have been changed for this screenshot for confidentiality purposes.
  • We've even built entire business case decks for our buyers to make it easier for them to get their leadership teams on board with the purchase.
This business value slide was part of a larger deck we created for a lead that later became a customer. Some names and numbers have been redacted for confidentiality purposes.

Another way to give buyers more confidence is to provide a money-back guarantee. If you end up not being able to deliver on what you sold the buyer, they can not only get out of their contract but also receive a refund for what they paid.

We had to do this for one customer this year. It was the closest thing we've ever had to a one-call close: we closed the deal in a record amount of time. Unfortunately, closing so quickly meant due diligence wasn't done on our side or the customer's to make sure our product could solve the buyer's problems.

After a couple of months of frustration on both the customer's side and ours, we realized we weren't going to be able to solve the customer's problems, so we gave them their money back. 

We took a hit in doing so given we'd spent time doing implementation, but it was the right thing to do. And what we learned helped us change our sales process to make sure we never run into the same situation again. 

2. Creating a shortlist is almost impossible

If you've ever shopped for software and tried to put together a shortlist, you've almost certainly run into an issue every buyer encounters: every product's website says it can do everything, and every product in the market sounds like it does the exact same thing as all of its competitors.

Buyers know this isn't true, but it takes ridiculous levels of detailed questioning and research to properly understand the true differences between the products.

How to fix it

Look back at the examples we provided in the last section. You should also make as many of those as possible public on your website:

  • Pay an unbiased third party to write a market guide for you and publish an ungated version of it on your website.
  • Publish detailed, honest comparison pages that you've carefully verified.
  • Link to in-depth resources from high-level landing pages. Let people do their own research rather than pointing every CTA on your site to your demo request page.

Spend the time really spelling out the differences between your product and the market. Not only will it help you create a better buying experience, but it will also improve the quality of your leads and shorten your sales cycle because you're not putting the onus of educating leads entirely on your sales team.

Of course, even if you're being entirely honest in what you publish on your site, it doesn't guarantee buyers will believe you, so it also helps to make it easy for them to connect with people who will provide an unbiased perspective.

For that, we've been watching Noble — a new product that shows leads which of their first-degree LinkedIn connections are your customers. This makes it easy for leads to reach out to people they know personally who already use your product.

3. There's a lack of transparent pricing

One of the most common complaints I heard from buyers was about products not listing their pricing on their websites and, instead, either forcing buyers into a demo to get the pricing information or holding the information hostage until the very end of the buying process.

Hiding pricing causes a number of issues on both sides of the fence:

  • Buyers end up in demos — or at the end of entire sales cycles — for products they could never have gotten budget approval for, which is an incredible waste of time for both the buyer's and vendor's teams.
  • Buyers suspect that they're getting a worse deal than other customers. This makes them either want to avoid the sales process altogether because they dislike negotiating or bring in a negotiator who forces the vendor to accept a deal that doesn't make financial sense for the business.
  • Some buyers won't consider a product at all if the pricing isn't listed. So they might never look into the product that would have best solved their problems, and you never get the opportunity to tell them why your product is the best.

How to fix it

Fixing this one is pretty simple: put your pricing on your website.

If you can't give complete transparency due to complexities with your software, you can at least provide what the starting cost is, like we do at TestBox:

This gives you both the ability to consider the customer's requirements/complexities and ensures you're typically speaking to buyers with the budget to purchase your solution.

It may also be worth considering partnering with a company like Vendr that helps buyers negotiate with vendors and gain confidence that they're getting a good deal.

4. Buying software is too time-consuming

Sellers hate lengthy sales cycles, and ironically, buyers hate them too.

As I mentioned before, most software buyers have an entire other job they're supposed to be doing. All of the time they spend researching, watching demos, negotiating, and making a business case is time taken away from all of the other things they still have to do.

How to fix it

In reality, all of the tips we've provided so far will reduce the length of time required to buy and sell software:

  • Providing more detailed information on your site will help buyers create their shortlists more quickly.
  • Being transparent with your pricing will allow buyers to disqualify you immediately if your fees are out of their price range.
  • Helping buyers put together their business cases and giving them resources to truly understand the market will help them make decisions and get buy-in faster.

These things will also help improve the quality of your leads, which may eliminate the need to force buyers to talk to an SDR before they meet with an AE — another time-consuming step.

Additionally, remember that most people are software-buying novices, so they may not be fully aware of what their organization will need to fully approve the purchase.

For example, in our guide on how to shorten sales cycles, presales leader Deepti Khemka recommends encouraging your prospects to talk to your competitors because procurement teams often won't sign off on a deal if multiple vendors aren't considered. This could delay deals because of procurement compliance.

There are also a lot of ways to use automation to speed up the buying process for everyone:

  • Use Calendly or Chili Piper to let people schedule time with your reps immediately after filling out your demo request form.
  • Use RFP software like Loopio or Responsive to automate the creation of RFPs, RFIs, and security questionnaires, making delivering these assets faster and more efficient while improving the accuracy of the assets delivered.
  • Use demo and POC automation software like TestBox to create personalized demos and fully functional POCs in seconds instead of waiting for SEs to build them manually.
  • Use a tool like Gong and/or the notes in your CRM to summarize conversations when passing leads from XDR to AE to SE to CS. This keeps leads from having to tell their whole life story every time they get on a call with a new person.

Finally, look for ways to avoid having to get dozens of people on every sales call to prevent conflicting schedules from slowing things down. Instead, provide buyers with summary materials or quick Loom videos they can share with other stakeholders asynchronously.

5. They're expected to just take your word for it

Our consumer expectations have increased but our B2B experience hasn't. You can try before you buy on Amazon, get clothes delivered to your house, try them on, and then ship them back for free if they don't fit right. So naturally, people get frustrated when things are so archaic when it comes to buying software for their businesses.

Buyers want to try before they buy. They want to see for themselves that your product does what you say it does and that your integrations will meet their needs. Giving them a hands-on experience creates the most confidence that your product will solve their problems.

How to fix it

There's another simple answer to this problem: let buyers try your software before they buy it. But for many companies, that's easier said than done.

Some companies simply don't have the technical infrastructure set up to be able to provide leads with a trial or POC. Doing so takes an incredible amount of work from either a solutions team member or a product engineer, so the ability to get hands-on with the tool is reserved only for the biggest ACV leads.

Other companies have incredibly complex products that are difficult to showcase in a trial, and letting leads in actually reduces the likelihood that those leads will close.

This is actually one of the biggest problems we're solving with TestBox. We work with companies to automate the process of creating POCs for them so they can send a POC to every lead — no matter the size of their contract — in just a couple of clicks. Additionally: 

  • We preconfigure POCs with realistic and personalized data to make the trial experience mimic the feeling of having the product fully set up. 
  • We set up functional integrations for the things buyers most commonly need to integrate. 
  • We add a quick links menu pointing to key product features and include a guided walkthrough explaining how to use those features so buyers never get lost.

If you need a way to let leads try before they buy but haven't had luck figuring out a way to do it — either because of technical constraints or usability complications — check out TestBox!

6. Most free trials are terrible

Often, the solution to the "leads want to try before they buy" problem seems like something that adding a PLG motion would fix. However, it's often really hard for sellers to create a PLG motion due to the technical complexity and the need to reorganize entire GTM motions.

Additionally, many of the buyers we spoke to expressed a lot of frustration with the PLG free trial process.

Most free trials are empty and overwhelming. To actually use the tool to see if it does what they need it to do, buyers have to spend a ton of time setting the tool up and adding data. And they have to do this multiple times if they're testing multiple products. 

How to fix it

To solve this, you could: 

  • Use product tour software like Pendo or Userpilot to create more helpful in-app onboarding guidance for new trialists.
  • Offer live classes for new trialists where you show them how to set up and use your product and give them a space to ask questions.
  • Automatically add sample data to all trials so buyers don't have to start from scratch.

Here are some more great tips on how to improve your free trial — plus examples from brands that do these things well — from the team at OpenView.

7. They don't really want to be sold to

No one wants to feel pressured to buy something. They want to buy it if they want or need it.

No one wants to fill out an online form and then get cold-called and emailed every week for the next year.

No one wants to be rushed into a decision because it's the end of the quarter and an AE needs to make their quota.

No one wants to be sold to.

How to fix it

So many of the things people hate about buying software stem from a lack of trust:

  • They don't trust that your reviews and testimonials are unbiased.
  • They don't trust that your software does what you say it does.
  • They don't trust that they're getting a good price.

This is why the key to success in 2024 and beyond is moving from a "close the deal at all costs" mindset to a "be a trusted advisor" mindset.

The reality is that no one actually wants to buy software to solve their problems. They just want to solve their problems. They don't care how that gets accomplished.

So to sell more software, you need to stop being a salesperson and start being an advisor. Be someone leads can trust. Be someone who guides them in the right direction. 

If you come at it from that perspective, it changes the entire lens of how you approach selling.

As salespeople, we're deep subject-matter experts on the products we're selling and the markets we're competing in. We're in the perfect role to help buyers who have no idea what they're doing figure out what they should be doing with so much confidence that all of their fears, frustrations, and reservations slip away.

As advisors, we earn the trust of our buyers. We get more leads, close more deals, and retain more customers because what we sell is what people need and what we deliver. 

No one wants to be sold to, but everyone wants to be advised. And it's in that way that we can truly fix all of the things people hate about buying software.

Watch our Chief Solutions Officer, James Kaikis, talk about the future of solutions based organizations

Watch the presentation to learn about the change that you can make within your organization.

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