Software Vendor Evaluation Checklist

Technical fit

They ran a real discovery conversation built around your problem, not a sales pitch built around their capabilities
You've had a technical conversation directly with the engineers who would work on your project, not only with a sales or account lead
They engaged with tradeoffs specific to your case (cost vs. flexibility, build vs. buy) instead of generic reassurance that they "can build anything"
They have relevant experience with your technology stack, or a demonstrably similar one

A communication cadence is agreed explicitly, in writing, before the engagement starts
You have a named point of contact who has real authority to make decisions, not just escalate them
You get visibility into progress by default — backlog or repository access, working demos — not only summaries after the fact
They can describe a specific past example of surfacing bad news early, not just a general assurance that they're "very transparent"

The proposed delivery model (fixed-price, time-and-materials, outcome-based) matches how well your problem is actually understood today
The estimate states the assumptions it depends on, not just a number with nothing to hold anyone accountable to later
The proposal states what's explicitly excluded from scope, not only what's included
The timeline is broken into milestones, not a single distant delivery date
You know how a scope change gets estimated, approved, and priced once work is underway

A written clause confirms all code, architecture, and custom tooling transfers to your ownership on payment, with no ambiguity
They've explained how access to your systems and data is controlled and revoked when someone rolls off the project
A mutual NDA is in place before any substantive technical detail about your business was shared
You know where your data is stored and processed, and whether that carries any compliance implications for your industry

You know explicitly whether staffing is a dedicated team or shared/bench staffing across multiple clients
You know the actual seniority mix of the assigned team and how hands-on the senior people named in the proposal will really be
You've asked directly about team turnover and got a specific, credible answer rather than a deflection

The engagement can scale up or down if your needs shift, without a costly renegotiation each time
The exit clause defines the notice period, what happens to work in progress, and how access and documentation are handed over
You understand how renewal works and whether early terms create any lock-in that would make switching providers harder later