Why Vendor Evaluation Matters
SaaS contracts are easy to sign and hard to exit. By the time you discover a platform's hidden limits — feature paywalls, poor support, sketchy uptime, or problematic data portability — you may be 12 months into an annual contract with significant data migration pain ahead.
A structured evaluation process prevents these surprises. Here's the checklist we use.
Section 1: Security & Compliance
- Do you maintain SOC 2 Type II certification? Can you share the report?
- Are you ISO 27001 certified?
- How is data encrypted at rest and in transit?
- Where is data stored geographically? Can we specify a region?
- How do you handle subprocessors? Who has access to our data?
- Do you support GDPR data subject requests (access, deletion)?
- What is your penetration testing cadence? Can we see results?
- Do you have a bug bounty program?
- How are employee access controls managed (MFA, SSO, least privilege)?
- What is your incident response process? What is your breach notification SLA?
Section 2: Reliability & Performance
- What is your historical uptime over the past 12 months?
- Do you have a public status page? Where can we see it?
- What are your SLA guarantees, and what remedies exist if they're missed?
- How do you handle planned maintenance windows?
- What is your disaster recovery plan? What is the RPO and RTO?
- How does performance scale as our usage grows?
- Are there usage limits (API rate limits, storage caps, user seats) that could affect us?
Section 3: Pricing & Contracts
- What is the full pricing model — per user, per usage, flat rate?
- What happens to pricing as we scale? Are there volume discounts?
- What is the contract length and renewal terms?
- Are there auto-renewal clauses? What is the opt-out notice period?
- Are there setup, onboarding, or implementation fees?
- What is included in each pricing tier, and what features require add-ons?
- What is your pricing history? Have you raised prices on existing customers?
- Are there discounts for annual prepay vs. monthly billing?
Section 4: Support & Success
- What support tiers are available (chat, email, phone, dedicated CSM)?
- What are the support hours? Is 24/7 support available?
- What is the guaranteed response SLA by severity level?
- Is there an onboarding program? What does it include?
- What documentation, training, and self-service resources are available?
- Is there a customer community or user group?
- Do you assign a dedicated Customer Success Manager? At what tier?
Section 5: Product & Roadmap
- How frequently do you release product updates?
- How is customer feedback incorporated into the roadmap?
- Can we view the public roadmap?
- How do you handle feature deprecation? What is the notice period?
- What is the history of major version migrations? Were they disruptive?
- Do you have a beta program for early access to new features?
Section 6: Integration & Data
- What native integrations do you offer with tools we use (listed them)?
- Is there a public API? What authentication methods are supported?
- What are the API rate limits?
- What data formats does the API support (REST, GraphQL, webhooks)?
- How do we export our data? What formats are available?
- Is there a bulk data export option? Are there any restrictions?
- Are there fees for data exports?
Section 7: Exit & Portability
- What happens to our data if we cancel? How long do you retain it?
- How long do we have to export our data after cancellation?
- What is the process for data deletion upon request?
- Do you provide transition assistance if we switch to a competitor?
- What are the penalties, if any, for early contract termination?
How to Use This Checklist
For small software purchases (<$10K/year): Focus on sections 1, 3, and 7. Security, pricing clarity, and exit terms matter most for every purchase. For mid-market purchases ($10K–$100K/year): Complete all seven sections. Request formal answers in writing as part of the procurement process. For enterprise purchases (>$100K/year): Engage your legal, security, and procurement teams. Commission a formal security assessment. Negotiate SLA terms and exit clauses before signing.Red Flags to Watch
- Unwilling to share SOC 2 report (even under NDA)
- Uptime SLA with only service credits, no exit rights for chronic failures
- Auto-renewal with short opt-out window buried in contract
- Data export only available in proprietary formats
- Vague answers about subprocessors or data residency
- No public status page or incident history
The Bottom Line
The best vendor relationships start with the right questions. A vendor that's confident in their product and practices will answer these questions readily. Hesitation or evasion on security, data portability, or contract terms is itself useful information — it's a signal of what the relationship will look like after you sign.