Buying AI Without Regret: How Leaders Should Evaluate Enterprise AI Investments

InnovationBuying AI Without Regret: How Leaders Should Evaluate Enterprise AI InvestmentsByEilon Reshef,Forbes Councils Member.for Forbes Technology CouncilCOUNCIL POSTExpertise from Forbes Councils members, operated under license. Opinions expressed are those of the author. | Membership (fee-based)May 15, 2026, 09:00am EDTEilon Reshef, cofounder and CPO of Gong, is a seasoned entrepreneur, executive and investor in the internet and software spaces. getty​The market for enterprise AI software has become, by any measure, overwhelming. New products arrive weekly, existing ones mutate with each model upgrade and the falling cost of building software means that every startup with a large-language model and a pitch deck now claims to be reinventing the category. For leaders acquiring these solutions, the result is a paradox of choice so acute that many have simply frozen in place.As a product leader, I am often asked how to evaluate these innovations to determine which ones are actually poised to deliver on their promises. A useful evaluation framework, therefore, needs to go beyond feature checklists or model sophistication and instead should assess how an AI product converts raw data and intelligence into tangible business results.One approach is to borrow the frameworks that product executives themselves use to build and position their offerings. Business leaders who learn to see the market through a solution provider’s eyes tend to ask sharper questions, filter out noise faster and avoid the costly regret of a misguided purchase.With that, here are five key principles that will help leaders determine whether they’re investing in AI tools that will deliver value—or slop.1. Start With The Job, Not The DemoThe most useful of these borrowed frameworks is known as Jobs to Be Done, a method popularized by the Harvard economist Clayton Christensen. Its central insight is deceptively simple: Customers do not buy products; they hire them to accomplish specific tasks. A commut...