OPERATIONS

When to stop renewing the SaaS — a buying-decision checklist.

Most SaaS renewals get rubber-stamped because nobody owns the question of whether the tool is still pulling its weight. Here's the checklist we use.

By Paul DiMaggioApril 20265 min read

The default for SaaS is renewal. The seat count creeps up, the price escalates 8–12% a year, and nobody has the time or political appetite to ask whether the thing is still earning its keep. Multiply that across thirty tools and you've built an operating expense problem you don't see.

The five questions

Before any renewal over $5K/year, force the owner to answer these in writing:

1. Who actually uses this in the last 30 days, by login record? Not by license assignment.

2. What workflow breaks if we turn it off tomorrow? Be specific — name the workflow, not the team.

3. Is the value here in the product, or in the data inside it? If it's the data, what's the export plan?

4. What did we pay last year, what are we being quoted now, and what's the three-year projection at the vendor's stated escalator?

5. What would we replace it with, and what would that migration cost in hours and dollars?

The dead-tool tells

A few signals that almost always mean it's time to cut: under 40% of licensed seats logged in last quarter; the original sponsor has left the company; the workflow it supports has been replaced by a feature in something else you already pay for; the vendor has been acquired and the roadmap has stalled.

None of these are automatic kills, but two or more in the same tool means you're paying for inertia.

Negotiate like you mean it

Vendors price renewals based on what you'll tolerate. Going into the call with a credible alternative — even a half-built migration plan to a competitor — typically clips 15–30% off the quote. Going in with nothing typically gets you the escalator.

If you're not willing to leave, you're not negotiating, you're just complaining politely.