Enterprise SaaS Evaluation Checklist: 50 Questions Before You Sign

Enterprise SaaS evaluations are expensive — in time, in opportunity cost, and in the risk of getting the decision wrong. This checklist is designed to systematize the evaluation process and ensure your team is asking the right questions at each stage.

Use this checklist for any tool with an annual contract value above $25K. For smaller purchases, use a simplified subset (security, integration, pricing).

Security and Compliance (10 Questions)

1. Does the vendor have SOC 2 Type II certification? (Request the most recent audit report, not just a badge)

2. Is a data processing agreement (DPA) available? (Required for any tool handling personal data under GDPR/CCPA)

3. What is the breach notification timeline in their DPA? (72 hours is the standard; anything longer is a red flag)

4. Who are the vendor's sub-processors, and are they listed publicly? (This defines the full chain of custody for your data)

5. When was the vendor's last penetration test, and by which firm? (Should be within the last 12 months for any security-sensitive tool)

6. Does the vendor support SSO via SAML 2.0 or OIDC? (Required for enterprise IT governance)

7. What encryption standards are used for data at rest and in transit? (AES-256 and TLS 1.2+ minimum)

8. Does the vendor have a published vulnerability disclosure policy?

9. Are HIPAA or FedRAMP certifications required for your use case, and does the vendor meet them?

10. What is the vendor's data residency policy, and can data be restricted to specific geographic regions?

Integration and Technical Fit (10 Questions)

11. What APIs are available, and what are the rate limits? (Request API documentation before the demo)

12. Is the integration with your CRM native or third-party middleware-based? (Native integrations are more reliable; middleware creates additional failure points)

13. What is the typical data sync latency between systems? (Real-time vs. batch sync has significant workflow implications)

14. What happens to integrations if the vendor releases a major platform update? (Get the vendor's upgrade and communication policy in writing)

15. Can the tool export all data in a standard machine-readable format? (JSON, CSV — this is your portability insurance)

16. Does the vendor have a publicly documented webhook system for event-driven integrations?

17. Are there known incompatibilities with your current stack? (Ask explicitly; vendors know their integration gaps)

18. What is the vendor's approach to API versioning and backward compatibility?

19. Does the vendor offer an integration guarantee or SLA for specific systems?

20. Are there limits on API calls or data volumes in your contract tier?

Pricing and Contract (10 Questions)

21. What is the all-in annual cost including implementation, training, and any per-usage fees?

22. How does pricing scale as your team or usage grows? (Get specific examples with your current and projected usage)

23. What is the annual price increase cap at renewal? (Negotiate to 5-7% maximum)

24. What is the auto-renewal notice period? (Understand and calendar this immediately upon signing)

25. Are there overage fees, and at what rates? (Negotiate overage rates into the contract before signing)

26. Is implementation and onboarding included, or priced separately?

27. What happens to pricing if you reduce the number of seats mid-contract?

28. What is included in each contract tier, and what requires a paid upgrade?

29. Is there a money-back guarantee or pilot period before the full contract commitment?

30. What are the termination conditions, and can you terminate for cause if the vendor materially changes the product?

Product and Roadmap (5 Questions)

31. What is the vendor's product development cadence, and how are customers informed of upcoming changes?

32. Can you speak to the product manager responsible for the features most critical to your use case?

33. What features on your must-have list are currently on the roadmap vs. currently available? (Get roadmap commitments in writing if possible)

34. How does the vendor handle feature requests from enterprise customers?

35. What has changed in the product in the last 12 months? (Ask for release notes or a changelog)

Support and Implementation (10 Questions)

36. What support tier is included in your contract? (Email, chat, dedicated CSM, phone — and what the SLA is for each)

37. What is the escalation path for critical production issues?

38. Is a dedicated implementation engineer included, and for how many hours?

39. What training resources are available, and are they included? (On-demand, live, documentation)

40. Can you speak to three reference customers of similar size who implemented in the last 12 months?

41. What is the typical time to value for companies of your size and complexity?

42. What is the vendor's customer success-to-customer ratio? (Higher ratio means less attention per account)

43. Does the vendor have a community forum or user group where customers share best practices?

44. What happens to your account if your CSM leaves or is reassigned?

45. What is the vendor's current CSAT or NPS score, and how has it trended?

Scalability and Future-Proofing (5 Questions)

46. What is the vendor's maximum known customer size in your industry, and does the product perform at that scale?

47. Does the vendor have a credible enterprise customer list in your vertical?

48. What is the vendor's funding status and approximate runway? (Relevant for early-stage vendors)

49. Has the vendor been subject to any significant security incidents in the last 24 months? (Check their status page history and public records)

50. What would a migration away from this vendor look like, and what would it cost? (Plan your exit before you commit)

How to Use This Checklist

Not every question requires the same depth of response. Prioritize:

• Must resolve before demo: Questions 1, 2, 11, 12, 21-22 (security basics and integration fit)
• Must resolve before pilot: Questions 3-10, 13-20, 23-30 (deeper security, integration details, and contract structure)
• Must resolve before signing: Questions 31-50 (product roadmap, support, references, scalability)

Maintain a consistent scoring system across vendors on the questions that matter most for your context. Vendors should be scored against the same criteria on the same scale — not remembered by impression of the demo.

Tools like Trackr can generate an initial research report on any vendor in under two minutes, covering key dimensions that map to this checklist — useful for quickly filtering your longlist before you invest hours in formal vendor questioning.

Bottom Line

A 50-question checklist sounds like overkill until you've signed a two-year contract for a tool that doesn't integrate with your CRM, auto-renews on 90 days notice, and whose vendor is burning cash. These questions exist because each of them has burned someone. Run through them before you're committed.

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