Here’s a practical checklist of features to look for when evaluating contract management software (CMS/CLM), grouped and explained so you can prioritize by need:

Core contract lifecycle features (must-haves)

• Centralized repository: single source of truth with full-text search and rich metadata so contracts are easy to find.
• Versioning & audit trail: automatic version control and an immutable, time-stamped history of who changed what and when.
• Clause library & templates: reusable, governed templates and pre-approved clauses to speed authoring and ensure consistency.
• Authoring & redlining: in-app drafting, collaborative redlining, and comparison tools for negotiation.
• Workflow & approval routing: configurable multi-step workflows, conditional approvals, and delegated sign-off.
• Obligation & milestone tracking: automated capture and reminders for renewals, notice periods, deliverables, payment terms, SLAs.
• E-signature integration: built-in or tightly integrated e-signature that is legally enforceable (ESIGN/eIDAS compliant).

Search, discovery, and metadata

• Advanced search: full-text, metadata, Boolean/faceted filters, and searchable scanned PDFs (OCR).
• Automatic metadata extraction: ability to auto-extract key fields (parties, dates, amounts, clauses) to avoid manual tagging.

Security, compliance & controls

• Role-based access control (RBAC) and least-privilege permissions.
• Encryption at rest and in transit (industry-standard TLS and robust encryption algorithms).
• Strong authentication options: SSO, SAML/SCIM, MFA.
• Audit logs & forensics: tamper-evident logs for compliance and legal discovery.
• Compliance certifications & policies: vendor adherence to standards you need (e.g., SOC 2, ISO 27001, GDPR, HIPAA if applicable).
• Data residency & retention controls: ability to meet jurisdictional/retention rules and legal holds.

Automation & intelligence (higher-impact)

• Automated workflows & auto-notifications: scheduled alerts, escalation rules, and auto-tasks.
• AI/ML-assisted clause extraction & review: auto-identify risky clauses, anomalies, or non-standard language (useful but validate accuracy).
• Auto-renewal control: detection of auto-renew terms and configurable guardrails.

Integrations & extensibility

• APIs & webhooks: reliable REST APIs and webhooks for bi-directional automation.
• Prebuilt integrations: CRM (Salesforce, MS Dynamics), ERP (SAP, Oracle), HRIS, procurement, billing, DMS (SharePoint), e-sign providers, and legal matter systems.
• Data export & import: simple bulk import/export in standard formats (CSV, Word, PDF, XML).

Reporting & analytics

• Dashboards & KPIs: dashboards for expirations, obligations, contract value, risk exposures, cycle times.
• Custom reporting & scheduled reports: ability to build ad-hoc reports and schedule distribution.
• Audit & compliance reporting: quick export of audit trails for legal/reporting needs.

Usability & adoption

• Intuitive UI & low learning curve: minimize training overhead so business users adopt it.
• Role-specific views: templates/dashboards for legal, sales, procurement, finance.
• Mobile access: read/approve/notify capability on mobile devices.
• Onboarding, training & documentation: in-product help, training, and good vendor enablement.

Deployment, scalability & operations

• Deployment flexibility: SaaS, on-premises, or hybrid depending on policy.
• Multi-entity & multi-language support: for global enterprises.
• Scalability & performance: handles your contract volume and search loads with acceptable latency.
• Backup, DR, and uptime SLAs: clear SLA and documented disaster recovery plan.

Legal & vendor considerations

• Clear pricing model: know per-user vs. per-contract costs, API call limits, and add-on fees.
• Contract portability: ability to export complete contracts and metadata if you switch vendors (avoid vendor lock-in).
• Sandbox/test environment: for configuration and user acceptance testing.
• Support & implementation services: professional services, migration help, and responsive support SLAs.

Nice-to-have / advanced features

• Redline negotiation automation (suggested edits).
• Playbooks and risk-scoring templates for fast triage.
• Clause-level permissions (who can change which clauses).
• Contract-centric collaboration spaces (chats, annotations).
• Bulk actions (mass renewals, mass upload tagging).
• Localization and currency handling for global businesses.

How to evaluate — quick rubric

• Must-have (score 1–5): core repo, search, versioning, approvals, e-sign, security, integrations.
• Important (score 1–5): auto-extraction, reporting, APIs, workflows, templates.
• Nice-to-have (score 1–5): AI clause analysis, negotiation automation, advanced analytics.
  Give must-haves higher weight and score each vendor; run a pilot with a real sample set of contracts.

Red flags to watch for

• No clear audit trail or weak versioning.
• Poor search/OCR (contracts become unusable).
• Closed system with no API or poor export—risk of vendor lock-in.
• Opaque pricing, unexpected per-feature fees, or per-contract charges that balloon costs.
• Lack of basic security features (no SSO, no encryption at rest, or no compliance attestations).
• Manual-heavy processes despite claiming automation.

Practical next steps

• Define top 6 “must-have” features for your org (e.g., obligations, e-sign, integrations to Salesforce/ERP, RBAC, search, templates).
• Run a short proof-of-concept using 50–200 representative contracts to test extraction, search, workflows, and reporting.
• Score vendors with the rubric above and confirm export/termination terms in the contract.

If you want, I can convert this into a one-page RFP checklist, a weighted scoring template in Excel format, or a prioritized short-list for a specific company size/function (legal, sales, procurement). Which would you prefer?