How Long Does a Software Evaluation Actually Take?

If someone has told you a software evaluation takes “a few weeks,” they haven’t done one. For a mid-complexity SaaS product, a well-run evaluation takes three to six months from start to signed contract. Here’s where the time actually goes.

The Five Phases

• Internal preparation (2–4 weeks). Requirements gathering, stakeholder alignment, and a day-one conversation with Procurement. Skip this and you’ll do it later — badly, under pressure.
• Market research and shortlisting (2–4 weeks). Identify credible vendors, issue an RFI, and narrow to three to five worth evaluating. Involve IT early enough to surface technical dealbreakers before they derail you.
• Active evaluation (6–10 weeks). Discovery calls, demos, proof of concepts, and reference checks across multiple vendors. Each touchpoint takes longer to schedule and debrief than expected.
• Internal alignment and approval (2–4 weeks). Getting leadership aligned, building your business case, and navigating approval processes. Board schedules and competing priorities add time you can’t always control.
• Legal review and contract (4–8 weeks). The most consistently underestimated phase. Brief your legal team early — before a vendor is selected, not after.

A Note on Seller Timelines

At some point your vendor will create urgency — a quarter-end deadline, a pricing window, an implementation slot filling up. Some of it is real. None of it is your emergency. You’re making a multi-year organizational commitment. It happens on the timeline that allows your organization to decide correctly.

The Bottom Line

Buyers who walk in with a realistic timeline make better decisions. Set your timeline before the first vendor conversation, share it with leadership, and protect it. A rushed evaluation doesn’t save time — it produces bad decisions you spend years managing.

If you’re navigating a software evaluation and want the complete insider’s playbook — how to manage vendors, negotiate the right terms, and build a business case that actually gets approved — The Accidental Buyer was built for this moment.

Learn more at accidentalbuyer.com