SMBs and enterprises face equal odds of software purchase regret, but their path there won’t be the same.
When we analyzed data from the 3,500 software buyers around the world that responded to Capterra’s 2025 Tech Trend Survey, we found that small and midsize businesses (SMBs, 5-999 employees) and enterprises (1,000+ employees) have a few things in common when it comes to buying software:*
Both expect to grow and increase their software budgets this year
Both plan to use their bigger budgets to bolster IT security and implement artificial intelligence (AI)
Roughly 60% of each made a regretful software purchase in the past 18 months
But it’s the differences in the sizes of these businesses that we find most interesting. Not only do SMBs and enterprises face vastly different software challenges entering 2025, but they also experience software purchase regret in different ways. Knowing what potential pitfalls await your size of business when buying software can help you avoid them.
Security is a top-of-mind concern for enterprises: Enterprises are more likely to consider the management and prevention of cybersecurity threats a top challenge in 2025, and more likely to cite security concerns as a top challenge when planning investments in new software than SMBs.
SMBs are let down at the implementation stage, while enterprises experience regret afterward: SMBs are more likely to blame their purchase regret on poor implementation than enterprises. Contrarily, enterprises are more likely to cite the product not being user-friendly and having poor technical support.
SMBs are concerned about cost, while small enterprises worry about productivity: SMBs cite increased costs as a result of a regretful software purchase more than any other impact, while small enterprises (1,000-4,999 employees) are most likely to say that a regretful software purchase caused a drop in employee productivity.
Note: Regretful software purchases are defined as purchases where buyers seek major remedial action, like replacing their system.
Though they have similar tech goals, SMBs and enterprises face different challenges
Entering 2025, both SMBs and enterprises are optimistic. In both groups, roughly 83% expect to grow over the next 18 months (82% for SMBs, 85% for enterprises), and nearly three out of every four plan to increase their software spend (75% for SMBs, 77% for enterprises).
They’re even planning to spend their larger software budgets on the same areas. The top three software tools SMBs and enterprises consider their top investment priorities are IT security, IT management, and artificial intelligence (AI).

But the impetus for these purchases differs, as do the challenges they expect to face with implementing them.
For SMBs, the problem is people. SMBs are 13% more likely to cite the availability of labor as a significant external factor shaping their business goals than enterprises. They’re also more likely to consider staff acceptance or training a top challenge when planning investments in new software. Focusing on tools like IT management and AI offers a way to bolster the productivity and efficiency of the few employees they have, but getting them up to speed on this new tech is a significant obstacle.
Meanwhile, enterprises are more concerned about the risks vs. rewards of the new tech itself and how it’ll pair with their existing software stack. They are 12% more likely to cite tech advancements as a significant external factor shaping their business goals than SMBs. They’re also more likely to say that implementing technologies effectively is a top challenge they expect to face in 2025.
Enterprises rely more on tech to stay ahead of the competition, but they’re also more mindful of the risks that come with a bad software implementation. Security, for example, is clearly more top-of-mind for enterprises. They’re more likely to consider managing and preventing cybersecurity threats a top challenge in 2025, and more inclined to cite security concerns as a top challenge when planning investments in new software. While a cyberattack is a threat to businesses of all sizes, enterprises appear more aware of their consequences.
This vigilance seems to stem from past experience, as enterprises in our survey cite IT security software as their top source of recent purchase regret.
Because they’re more likely to lack dedicated trainers or IT experts, SMBs need to plan ahead to ensure they have the right people to find and research different software products, and also the right people to use software effectively. For this reason, SMBs need to more closely evaluate things like setup guides, support materials, and how much vendors will help train new users when comparing different products.
Enterprises, on the other hand, need to be wary of implementing new tech “just to stay ahead.” Buyers should have a clear internal goal in mind with every software purchase (clarifying goals and desired outcomes is the top change regretful software buyers would make to avoid regret in the future). Enterprises are also more likely to say they would ensure alignment on product evaluation/selection criteria to avoid regret on future purchases than SMBs, indicating the need to more clearly define feature needs and integration requirements from the outset.
Poor implementation plagues SMBs, while enterprises blame unintuitive interfaces
SMBs and enterprises alike are aiming to avoid a regretful software purchase with their bigger budgets this year. However, the factors likely to cause that regret differ.

Comparing the SMBs and enterprises in our survey that have experienced purchase regret before, we find that SMBs are more likely to blame their regret on poor implementation than their larger brethren. As we mentioned before, SMBs often lack dedicated IT personnel. As a result, they rely more on vendors than enterprises to get their software up and running, which can lead to problems or delays. This explains why SMBs are also more likely to cite their vendor not meeting promised deadlines as a reason for their regret (31% vs. 28%).
Enterprises, meanwhile, experience more of their issues after implementation. They’re more likely than SMBs to cite the product as not being user-friendly and poor technical support for their regret. At the same time, they’re also more likely to blame a product for being too basic for their needs, which points to the conflicting needs of larger businesses. They need software that has more advanced functionality without sacrificing user-friendliness, which can be difficult to find.
Plus, with more boxes needed to check, enterprises are more likely than SMBs to say that their vendor over-promised and under-delivered (39% vs. 35%).
SMBs need a vendor that can handle more of the technical setup and maintenance load, so this is something they should prioritize during their software search. Read reviews that mention implementation and take advantage of the free trial period any vendor offers to see if you run into any issues during your initial time using the product.
Speaking of free trials, enterprises need to take advantage of them even more than SMBs to accurately judge user-friendliness. Even a few annoyances or complicated workflows can add up to big problems when you factor in all of the employees who will need to use the software. Finally, enterprises should exercise patience. Getting users trained on a more advanced system takes time, and businesses shouldn’t rush to start the process over if they run into issues.
Regretful purchases impact SMBs and enterprises differently
Not only do the causes of purchase regret differ between SMBs and enterprises, but so do the effects. Knowing the impacts businesses feel from a regretful software purchase can help you avoid these devastating setbacks at your own business.
Running an SMB can feel like piloting a rocket ship: while you’re experiencing explosive growth, you can’t escape the feeling that one wrong move could prove disastrous. Operating on thin margins and without the financial resources of their larger counterparts, SMBs tend to be more cost-conscious. So, when these businesses make a regretful software purchase, the feeling they get most often is that they’ve wasted money.

A major driver of this feeling is a lack of experience with buying business software. The cost of the software license itself makes up the bulk of the price, but there are often additional costs for things like user training, data migration, and premium customer support. SMB buyers that don’t know that end up getting sticker shock and regretting their purchase.
To sidestep this, make sure you understand the total cost of owning software before you purchase your next system.
Small enterprises risk drops in security and productivity
At the enterprise level, the top impacts of a regretful software purchase differ between small (1,000-4,999 employees) and large (5,000+ employees) enterprises. Small enterprises are the business size most likely to say their regretful purchase caused a security vulnerability. They’re also the most likely to say their regretful purchase reduced employee productivity.

Because their regret is most often tied to IT security software, it makes sense that security vulnerabilities pop up often. It’s not enough to trust vendors that say your data will be secure anymore—buyers need to prod them on specific aspects of security to ensure the product they purchase won’t leave them exposed.
And with small enterprises being the most likely to say they experienced a problematic handoff between sales and implementation teams after they made their purchase, the most likely culprit for their drop in productivity is a bungled setup. To ensure you don’t hit any snags on the way to becoming fully productive with new software, ensure you stay in constant communication with your vendor during the implementation process.
Large enterprises face adoption difficulties and risk falling behind the competition
Because they have the resources to do so (money, infrastructure, expertise, etc.), large enterprises are often the ones leading the way in business technology. This makes every purchase decision more complex and opens up the door for other enterprises to make massive strides in market share when they bet on the wrong tech.
As a result, when large enterprises experience purchase regret, they’re most likely to face adoption difficulties and feel like they’ve fallen behind competitors.

Adopting unproven technology to stay ahead of the competition is risky for any large enterprise. To improve the odds of success, the top change regretful large enterprise buyers would make to avoid regret in the future is clarifying goals and outcomes.
Hiring the right consulting firm can also bring in the right people to lend insight and guide you when buying bleeding-edge technology.
Our e-book has all the tips you need to be a successful software buyer, regardless of size
We’ve talked about how SMBs and enterprises face different challenges entering a software purchase, and experience different effects when they make the wrong decision after the fact. But what can you do while you’re actually researching and evaluating different software options to avoid a regretful purchase?
For that, we offer you our 2025 Tech Trends e-book. In this downloadable report, we analyze what separates successful and regretful buyers at every stage of the purchase journey. We look at how many vendors they consider at each stage, the purchase factors they prioritize, and the information sources they trust the most to help them make decisions.