Why the CMMS market shifted in 2025–2026
Three things changed the evaluation calculus for maintenance management software over the last 18 months.
AI-generated work orders. Most mid-market CMMS vendors now ship some form of AI work order drafting. The question is no longer whether AI is present — it's whether it's actually useful or just marketing copy. Ask to see it in a live demo with your asset types, not a canned scenario.
Consolidation among vendors. Several CMMS platforms were acquired between 2023–2025. This matters for your decision: an acquired product may lose its roadmap, its support team, or its pricing model within 18 months. Check when the acquisition happened and ask directly what has changed.
Mobile-first expectation. Technicians now expect the mobile experience to be primary, not an afterthought. Legacy platforms built for desktop-first still ship mobile apps, but you can usually tell within 10 minutes of use. Run any evaluation with the mobile app on the actual device your technicians use.
12 questions to ask every vendor
Ask these in a demo call, not over email. How a vendor answers under light pressure tells you as much as the answer itself.
“What happens to our data if we cancel?”
Why it matters: You want a clear, specific answer: full export in a portable format (CSV, JSON, XML) within 30 days of cancellation, at no charge. Vague answers here are a yellow flag.
“How long does a typical implementation take?”
Why it matters: The right answer depends on your complexity. For 1–3 sites: 2–4 weeks. For 10+ sites: 6–12 weeks. Be suspicious of anyone who says "a day or two" for complex environments, or "6 months" for simple ones.
“Can you show me the mobile app on Android and iOS right now?”
Why it matters: Many vendors demo on desktop and show mobile screenshots. Ask them to open the actual app on a real device during the call. Watch for load times and offline behavior.
“What does your uptime SLA commit to, and what happens when you miss it?”
Why it matters: 99.9% sounds good but is ~8.7 hours of downtime per year. Ask what the SLA credit actually is — most offer meaningless 10% monthly credits. For critical operations, you want 99.95%+ with teeth.
“How do you handle custom asset types we haven't defined yet?”
Why it matters: Your asset list will grow. You need a system where adding new asset types, custom fields, and PM schedules doesn't require a support ticket or professional services.
“Walk me through how a technician gets assigned and closes a work order end-to-end.”
Why it matters: This is the most important workflow in any CMMS. Count the taps on mobile. If it takes more than 4–5 taps to close a work order, adoption will suffer.
“Can you show us how the API works and what it can and can't do?”
Why it matters: Even if you don't plan to integrate today, you will eventually. A read-only API is not an integration-ready API. You want full CRUD access to work orders, assets, and PMs.
“What does your pricing look like at 2×, 5×, and 10× our current user count?”
Why it matters: Vendors often have low entry pricing and steep growth curves. Get a written quote for your expected headcount in 2–3 years, not just today's.
“How does the system handle assets at multiple sites with different managers?”
Why it matters: Multi-site, multi-manager setups expose architectural limitations fast. You want role-based access that restricts by site without requiring duplicate accounts.
“What reporting do we get out of the box, and what requires custom configuration?”
Why it matters: Every CMMS claims "powerful reporting." Ask to see the top 10 pre-built reports and whether you can export them to CSV or connect to Power BI / Looker without a paid integration.
“How many customers similar to us went live in the last 12 months, and can we speak to two?”
Why it matters: References should be companies in your sector and size range that went live recently — not a success story from 2019. If the vendor hesitates, ask why.
“What's on your 12-month roadmap and how much input do customers get?”
Why it matters: You're evaluating a partner, not just software. A vendor with a published roadmap, a customer advisory board, or a public feature voting board takes product feedback seriously.
What “enterprise-ready” actually means
Every CMMS vendor claims to be enterprise-ready. It's meaningless marketing unless you define it. Here's what the term should cover for a 50–500 person operations team:
How to run a 30-day proof of value
A free trial without structure is just a product tour. A structured 30-day POV gives you a clear go/no-go decision with defensible data. Here's the framework:
- Import a representative subset of assets (one site, 200–500 assets)
- Create PM schedules for the 5 most common task types
- Add your top 5 technicians and verify mobile access
- Define success metrics in writing before you start
- All work orders for the pilot site go through the system (no parallel spreadsheets)
- Technicians close work orders via mobile only
- Manager reviews daily: are work orders closing, are PMs getting scheduled?
- Log every friction point — don't fix them, just record them
- Pull the weekly PM completion rate report
- Test any integrations you need (ERP, accounting, parts ordering)
- Have your IT team review SSO and security settings
- Re-run the 12 vendor questions with live data in front of you
- Measure actual vs target: time to close a work order, PM completion %, technician adoption rate
- Present findings to stakeholders with data, not anecdotes
- Get a final pricing quote locked in writing
- Make the go/no-go call
Red flags to watch for
Scoring your shortlist
Score each vendor 1–5 on these eight dimensions. Weight them by what matters most to your team. This gives you a defensible scorecard to present to stakeholders — not just a gut feel.
| Dimension | What to evaluate | Weight |
|---|---|---|
| Mobile UX | Tap count to close a work order. Offline capability. Load speed. | High |
| PM scheduling | Flexibility of frequency rules. Bulk editing. Calendar view. | High |
| Asset hierarchy | Parent-child assets. Custom fields. Multi-site organisation. | High |
| Reporting | Pre-built reports. CSV/BI export. Scheduled delivery. | Medium |
| Integration | API scope. Native integrations. Webhook support. | Medium |
| Security / compliance | SSO, RBAC, audit log, data residency. | Medium |
| Implementation | Time to go live. Migration tooling. Onboarding quality. | Medium |
| Total cost | Per-seat at 2× growth. Pro services required. Data export fees. | High |