Software buyers in 2025 are more informed, more cautious, and more willing to reconsider their buying decisions mid-flight than ever before.
Gartner’s latest research, based on insights from 3,500 buyers, paints a fascinating picture of how organizations approach software investments. While the landscape is filled with opportunities, it also presents significant challenges that software vendors must navigate strategically.
The good news? Software spending is on the rise. A staggering 82% of buyers plan to invest more in software this year than they did in 2024, with IT security, IT management, and AI leading the way.
The Path to Consideration
For software vendors, the battle begins long before a deal is closed. The purchasing journey starts with an initial shortlist of 4.4 vendors, and in most cases, buyers ultimately purchase from this list. The factors that influence which vendors make the cut are clear: reputation and past experience matter. More than half of buyers (53%) cite vendor reputation as a key determinant, while 48% rely on previous interactions with a company when forming their initial list.
However, getting on the shortlist isn’t enough. The research shows that 83% of buyers modify their initial list after conducting further research, with more than a quarter making significant or complete changes. Reviews play a critical role in this decision-making process — 41% of buyers actively seek out customer reviews to refine their shortlist. This underscores the importance of customer advocacy, as peer experiences shape perceptions and directly impact purchasing decisions.
The Evaluation Process
Once a vendor makes it onto the shortlist, the real work begins. Buyers don’t rush into decisions. On average, they actively engage with 2.5 vendors—whether through discussions, demos, or trials—over a span of 4.6 months. This lengthy evaluation period reflects the complexity of software buying decisions and the need for thorough due diligence.
Despite the prominence of product-led gro
wth (PLG), which remains the top factor for 62% of buyers, other elements play a crucial role. Buyers pay close attention to the quality of vendor support, the effectiveness of product demos, and the engagement of the sales team. This suggests that while PLG remains influential, human-driven interactions still have a meaningful impact on purchasing decisions.
The Challenge of Post-Purchase Regret
Even with all this careful evaluation, many buyers still experience regret after making a purchase. A shocking 59% report regretting at least one software purchase in the past 18 months.
Certain categories, such as security, marketing and communications, HR, finance, and sales, see particularly high levels of regret.
The reasons behind this dissatisfaction are strikingly consistent: unexpected cost increases, security vulnerabilities, productivity declines, adoption struggles, and competitive disadvantages.
Why a Value-Led Growth Strategy Matters
While product-led growth remains a dominant strategy, these findings highlight why software vendors must take a broader approach. A Value-Led Growth (VLG) strategy offers a way to not only secure deals but ensure long-term satisfaction and retention. Unlike a purely product-driven approach, VLG focuses on aligning solutions with business outcomes, ensuring buyers see clear and measurable value.
Instead of relying solely on product trials and demos, vendors must demonstrate how their software delivers tangible results. Clear pricing models, transparent ROI metrics, and customer success strategies can help mitigate post-purchase regret. By proactively addressing concerns about cost, security, and adoption, vendors can build trust and foster long-term relationships.
Implications for Sales, Marketing, and Customer Success
For sales teams, this means shifting the focus from selling features to selling outcomes. Rather than just guiding buyers through a demo, reps must help them envision how the software will drive success in their specific business context.
Marketing teams must prioritize credibility, leveraging customer testimonials, case studies, and ROI-driven messaging to reinforce value. Since peer reviews hold significant weight, cultivating strong customer advocacy programs can be a game-changer.
Meanwhile, customer success teams have a crucial role in reducing post-purchase regret. Ensuring smooth implementation, driving adoption, and continuously reinforcing value can prevent churn and turn buyers into long-term advocates.
The Bottom-Line: Future of Software Buying
The 2025 software buying landscape is both promising and challenging. Vendors that embrace a Value-Led Growth approach—one that goes beyond just a great product and focuses on delivering meaningful business impact—will not only win more deals but build lasting customer relationships. In an era where buyers are more informed and selective than ever, those who can prove their value will come out on top.
Sources: Gartner –https://www.gartner.com/en/digital-markets/insights/2025-software-buying-trends
