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Why Enterprise Software Deals Die: The Brutal Truth About Each Sales Stage (And How to Fix It)

Why Enterprise Software Deals Die: The Brutal Truth About Each Sales Stage (And How to Fix It)

Enterprise SaaS sales deals don’t die randomly — they die predictably at each stage of the funnel. Based on data from 250 enterprise software opportunities, this post breaks down exactly where deals collapse — discovery (35%), qualification (28%), needs assessment (22%), proposal (12%), and contract (3%). For pre-seed and seed-stage CEOs, the brutal truth is that 69% of qualified deals will fail unless you fix your sales process. From poor discovery and budget ghosting to technical misalignment and ROI confusion, every stage has a killer that can be prevented with the right frameworks. This guide gives you practical scripts, qualification gates, and coaching advice to dramatically improve your close rates. If you’re tired of seeing promising demos vanish into thin air, this is the no-BS playbook to stop your pipeline from becoming a graveyard — and start winning enterprise customers.

“Why the Dawn of Autonomous Procurement Is Still a Mirage”

“Why the Dawn of Autonomous Procurement Is Still a Mirage”

The narrative that “software buys software” oversimplifies enterprise reality. While Jeff Morris Jr. argues that procurement is shifting to AI agents making algorithmic, impersonal buying decisions, the evidence says otherwise. AI agents today are experimental, risky, and far from handling the complexity of multimillion-dollar enterprise deals. Trust, relationships, compliance, and governance remain central to software procurement. Instead of replacing sales teams, AI is emerging as a co-pilot—augmenting research, recommendations, and workflows. Authoritative sources like Reuters, Goldman Sachs, and Gartner emphasize that full autonomy in procurement remains speculative. Enterprises still rely on human judgment, negotiation, and accountability. This blog explores why algorithmic procurement is a mirage, not a present reality, and why hybrid, human-in-the-loop models are the real future. For SaaS founders and executives, the takeaway is clear: invest in AI augmentation, but don’t abandon the sales craft that still drives trust and deals.