Objective reviews and free trials go a long way in preventing purchase regret.
According to Capterra’s 2025 Tech Trends Survey, nearly half (48%) of retail businesses of all sizes experience software purchase regret, largely due to insufficient pre-purchase research. But retailers don’t have to stay trapped in a cycle of bad software purchases.
By analyzing major trends emerging from the buying strategies and hindsight recommendations of over 350 retail industry professionals, you can take steps to refine your software purchasing strategy and put your business on a path to growth.
73% of retailers will spend more on software in 2025 than they did in the past year.
48% of retailers regret one or more software purchases from the past 18 months.
88% of regretful software buyers say they’re likely to buy software solely based on info they get from vendors.
The top two business challenges retailers expect to face in 2025 are managing and preventing cybersecurity threats (39%) and implementing technologies effectively (37%).
Retailers will continue increasing their software investments in the next year
Within just the past few years, retailers have gained access to cutting-edge technology and enhanced automation to improve operations, marketing, and customer service—think IoT-based store monitoring tech, digital signage, and a variety of seamless payment methods.[1] Though there has been some undeserved hype around artificial intelligence, some specific use cases are a slam dunk for retail, such as conversational AI chatbots, social monitoring, and AI-driven personalization.[2]
Retailers are often eager adopters of emerging tech, and are uniquely positioned to incorporate customer-facing technology as part of their brand identity. Sephora’s Virtual Artist, Google’s AI-generated clothing models, and Instacart’s wayfinding app feature are a few examples.
For the past two years, Capterra has documented an annual increase in software investment across the retail industry (though not limited to emerging tech). Retail industry leaders will continue this trend in 2025, with 73% of retailers planning to spend more on software than they did last year. They’ll prioritize investments in IT and cybersecurity, artificial intelligence, retail management, and customer relationship management (CRM) software.
Nearly half of retailers experience software purchase regret—but it’s preventable
Alongside that increased investment, there has also been a steady incidence of software purchase regret. Nearly half (48%) of retailers regret one or more software purchases made in the last 18 months.
The impact of a regrettable software purchase can’t be ignored: In fact, 63% of regretful buyers describe the financial impact of their bad investment as significant to monumental. A bad purchase typically leads to increased costs, adoption difficulties, reduced productivity, and security vulnerabilities. In some cases, it can even lead to a competitive disadvantage.
The anatomy of a regrettable software purchase commonly includes unmet expectations around end user experience and unforeseen costs—issues often created by vendors who over-promise in the sales phase and underdeliver when the buyer is handed off to implementation and onboarding support teams.
What’s less obvious is that this huge incidence of purchase regret is preventable; too often, it results from a lack of objective pre-purchase research. Compared to successful buyers who don’t experience purchase regret, regretful buyers are far more likely to rely on subjective information about vendors and products when making purchase decisions.
For instance, 40% of regretful buyers decide what to buy based on information sourced from social media, compared to just 18% of successful buyers. And an astonishing 88% of regretful buyers say they’re likely to buy software solely based on information they get directly from vendors—a tactic that correlates strongly to purchase regret.
Successful buyers take their time to consider objective and qualified sources about software, such as verified reviews and recommendations from industry experts. Relying on a variety of sources, rather than just what social media or vendors tell you, makes you more likely to choose the right software for your business.
To buy the right software, do the right kind of research
By analyzing the research methods of successful buyers, and taking note of what regretful buyers say they’d do differently on their next purchase journey, there are a few takeaways to help retailers make the most of their pre-purchase research.
Regretful buyers wish they’d clarified goals and been flexible with their vendor list before purchasing
When asked what they’d change about their software selection process to prevent more bad investments from happening in the future, regretful buyers most frequently say they’d clarify goals and desired outcomes for their purchase (40%) and be more willing to update or change their initial vendor list (34%).
Staying focused on what you need your new software to do, and doing research to find highly rated products that match those expectations, can help prevent you from falling for ill-fitting options that are cheaper or flashier. Similarly, a pre-existing relationship with vendors isn’t necessarily a guarantee that your next investment will be a successful one. Be flexible with your shortlist as you do your research and stay open to vendors you’re less familiar with so you have more opportunities to find the right fit.
Successful buyers consider objective sources of product information
When looking to purchase software, successful buyers tend to begin with an informal list of vendors assembled based on factors such as vendor reputation (63%), previous experience with a vendor or product (55%), and having seen the vendor or product at a conference or trade show (36%).
Successful buyers don’t stop there—they conduct formal pre-purchase research to whittle the options down to around three vetted vendors.
The most influential information source successful buyers rely on to create their shortlist is customer reviews. Verified reviews from real buyers provide an objective view into the end user experience that you’re unlikely to get from vendor websites or social media accounts. Capterra provides thousands of verified customer reviews across dozens of software categories, so you can hear from businesses like yours about what works for them.
Successful buyers stay flexible, adding and subtracting vendors from their list as they read reviews, browse comparison websites, and discuss their options with colleagues.
By comparison, regretful buyers are more likely to rely on potentially biased sources of information about vendors and products, such as a vendor’s social media presence. In fact, the vast majority (88%) of regretful software buyers say they’re likely to buy software solely based on info they get from vendors.
Successful buyers seek out first-hand experiences with vendors and products
After arriving at a shortlist, successful buyers choose a couple of vendors to engage with—through conversation, product demos, or, most often, free trials of the software they’re interested in.
Using free trials to see how software works specifically for your business can reveal shortcomings you might not discover in speaking with sales reps. You can vet the products on your shortlist for the top product-related causes of purchase regret, such as a lack of user-friendliness, poor tech support, and unexpected costs, such as additional features your business may need that add to the overall cost of adopting the software. You’ll also get a sense of whether your vendor has set appropriate expectations about their product’s performance.
While engaging with vendors, it’s helpful to use a software comparison chart to track notes from your discussions about cost, features, support, training, and specifications about the software you’re considering. Capterra offers a software comparison chart you can use as you consider each vendor on your shortlist.
Business size may affect your company’s software buying strategy
Best practices notwithstanding, purchase strategies aren’t one-size-fits-all. The size of your business helps determine the highest-priority challenges it faces, and influences your software purchase decisions.
For instance, most retailers expect to deal with a host of common business challenges and external influences in 2025, chief among them managing cybersecurity threats and responding to technological advancements.
But looking more closely at characteristics based on business size reveals varying expectations about the impact of these challenges.
Tend to have a harder time hiring compared to large enterprises.
Are significantly more likely to be in a state of stasis or decline, rather than growth, over the next 18 months.
Most likely to face challenges funding software investments.
Typically put one person in charge of making software purchases on behalf of the company.
If you’re buying on behalf of a small business, you’re likely working on your own, with a more limited budget, and simultaneously dealing with other big challenges such as hiring and training employees. You may have less time and fewer resources to spend researching software compared to someone working on a team of buyers at a higher-earning company.
Given this, you may be tempted to take information from vendors at face value—but don’t. Spend some time browsing verified reviews to ensure you’re getting the most out of your smaller budget. You may not need the newest or most robust options on the market, but you shouldn’t settle for low ease of use, insufficient features, or poor customer support from your vendor.
You should also make a habit of considering cybersecurity anytime you purchase software. Your business may be small, but it’s still vulnerable to external threats.
Most likely to cite labor (i.e., cost and availability) as a significant external factor shaping their business goals.
Just like large enterprises, midsize retailers are more likely than small businesses to cite cyber threat prevention as a top challenge for 2025.
In our sample, the midsize businesses and large enterprises tend to be older than the small business cohort. Across surveyed industries, older businesses are more likely to have concerns about security, more likely to prioritize investments in AI, and less likely to experience software purchase regret.
If you’re buying software on behalf of a midsize retailer, your company is likely growing fast—and you need to buy software to keep up with your expanding operations. Hiring and employee management are still the biggest challenges facing your company, along with converting new customers. Managing cybersecurity threats has become more important as the company continues to grow, and you may have more bandwidth to consider investments in cutting-edge tech. You may be working alone or on a team of purchase decision-makers, but because you have limited time, you primarily consult vendor websites when narrowing your software options down to a shortlist.
It’s important to invest in software that will support your business through its growth phase. When researching vendors and products, consider verified reviews from businesses with needs similar to yours, and get answers on how pricing may change as you add seats or features to your subscription.
Tend to be more responsive to technological advancements.
Most likely to be looking into the adoption of emerging tech such as GenAI.
Along with midsize businesses, large enterprises are more likely to have teams of people responsible for software purchase decisions, rather than an individual buyer.
If you’re buying software for a large enterprise retailer, you likely have more decision-making support, either in the form of a purchasing team or conversations with industry peers and colleagues. You are under pressure to find a product that integrates well with a sizable existing tech stack and does not introduce any cybersecurity weaknesses. At this point in your company’s growth, you put more stock into previous experiences with vendors or products when considering new software investments, and you can probably afford industry-leading options. You’re likely considering investments in cutting-edge tech such as AI as a way to earn a competitive advantage, though you may face more internal obstacles to adoption as stakeholders weigh the risks and benefits of investing in unproven technology.
When doing your pre-purchase research, it is more important than ever to consider how your competitors are investing in customer-facing technology. You should take the time to test out software using trial periods, particularly if it’s a new category of software your company hasn’t tried before.
By understanding your business’s unique challenges and place in the retail landscape, you can tailor your software purchasing strategy to better support your goals.
Update your software purchase strategy to make satisfying investments in 2025
Like the majority of retailers, you probably plan to increase your software investments in the coming year. Whether that’s upgrading core systems or trying out an emerging technology such as generative AI, be sure your strategy involves best practices gleaned from successful sellers.
Make sure you read verified reviews, stay flexible when creating your shortlist, and take advantage of free trials to get a better impression of how the options you’ve identified will perform for your business.
Check out these additional resources to make sure your next software purchase goes smoothly, from research to onboarding.
