Here’s a compact, actionable checklist of features to look for when evaluating contract management software, grouped by priority and use-case, with brief why-it-matters notes.

Must-have (core functionality)

• Centralized repository: single source of truth for all contracts with structured metadata (parties, dates, value, status). — Prevents silos and lost documents.
• Advanced search and filtering: full-text search, metadata filters, and saved searches. — Speeds retrieval and risk reviews.
• Version control & audit trail: automatic versioning, check-in/out, and an immutable audit log of who changed what and when. — Essential for accountability and compliance.
• Document storage & file-type support: PDF, Word, scanned images. — Practical interoperability.
• Workflow & approval routing: configurable workflows, multi-stage approvals, role-based routing and escalation. — Ensures consistent review and reduces bottlenecks.
• Alerts & lifecycle notifications: reminders for renewals, expirations, notice periods, and milestone triggers (email/phone/Slack). — Reduces automatic renewals and missed obligations.
• Contract authoring & templates: clause library, pre-approved templates, and clause-level controls. — Speeds drafting and enforces legal standards.
• E-signature integration or built-in e-signature: compliant with ESIGN/UDES or equivalent. — Enables fully digital execution.
• Permissions & role-based access control (RBAC): granular read/edit/share permissions, segregation of duties. — Protects sensitive information.
• Reporting & dashboards: standard and customizable reports (expirations, obligations, contract value, bottlenecks). — Enables management visibility and decision-making.
• Security & encryption: at-rest and in-transit encryption, secure key management. — Protects confidential data.
• Scalability & performance: handles your current volume and growth without major performance degradation. — Avoids replatforming.

Important (productivity, risk reduction)

• Optical Character Recognition (OCR): extract text from scanned contracts to make them searchable. — Critical if you have legacy paper/scan contracts.
• Obligation & clause extraction: automated extraction of key dates, indemnities, auto-renewals, and obligations (manual review still required). — Speeds risk triage.
• Redlining & compare tools: easy side-by-side comparison of versions and change tracking. — Speeds negotiation.
• Integration ecosystem: native or API-based integration with CRM (Salesforce), ERP, procurement, HR, finance, SharePoint, Google Workspace, Box, and SSO/IdP (SAML/OAuth). — Prevents duplicate data entry and supports process automation.
• Single sign-on (SSO) and MFA: simplify login and improve security posture.
• Permissions-based clause approval: allow legal to lock or require sign-off on specific clauses. — Maintains legal control while enabling self-service.
• Role-specific UI & templates: tailored views for legal, sales, procurement, finance. — Improves adoption.

Nice-to-have (advanced/AI/efficiency)

• AI-assisted drafting & clause suggestions: auto-suggest clauses, generate summaries, or propose redlines (verify outputs). — Can save time; validate accuracy.
• Automated contract obligation monitoring: continuous tracking and automated task assignment when obligations come due.
• Playbooks & negotiation guidance: embedded negotiation rules for sales/procurement to follow.
• Bulk upload & mass redaction: import many contracts and redact sensitive data in bulk.
• Contract scoring & risk dashboards: risk-scoring model that flags high-risk agreements.
• Multi-jurisdiction & multi-language support: for global organizations.
• Sandbox/test environment & audit logs for admins: safe change testing and compliance.

Compliance, governance & legal controls

• Data residency & localization options: support for regional data-storage requirements (if relevant).
• Retention & disposal policies: legal hold, retention schedules, and defensible deletion.
• Role-based audit reporting: exportable logs for internal/external audits.
• Certification and standards: SOC 2, ISO 27001, GDPR compliance statements if applicable.

Usability & adoption factors

• Intuitive UI and low learning curve: faster adoption across teams.
• Mobile accessibility: web/mobile apps for approvals on the go.
• Training & onboarding support: vendor-provided onboarding, documentation, and change management help.
• User activity analytics: track adoption, bottlenecks, and training needs.

Commercial & operational considerations

• Pricing model transparency: per-user vs. per-storage vs. per-feature — watch for surprise charges.
• Implementation time & professional services: realistic timeline and cost for initial setup, clause library build, and integrations.
• Data migration support: tooling and services to import legacy contracts and metadata accurately.
• SLAs & support: response times, local support availability, and escalation processes.
• Vendor stability & roadmap: company track record, references, and product roadmap alignment.

Evaluation tips and quick rubric

• Run a pilot with real contracts and workflows (not just demos).
• Test 3 core scenarios: create/approve/execute a contract; find a clause and extract obligations; report on renewals and contested terms.
• Score each vendor 1–5 on: Security, Workflow Fit, Search/Extraction, Integrations, UX, TCO (total cost of ownership), and Implementation risk.
• Red flags: no audit trail, limited search/OCR, closed ecosystem (no APIs), unclear pricing, or lack of e-signature compliance.

One-page checklist you can copy into an RFP

• Repository, Search/OCR, Versioning, Audit Trail, Workflows, Alerts, Templates/Clauses, E-signature, RBAC, Integrations (CRM/ERP/SSO), Reporting, Security (encryption, SOC2/ISO), Data residency, Retention/Legal hold, API, Bulk import/migration, Support & training, Pricing model, Roadmap & references.

If you want, I can:

• Turn that checklist into a prioritized RFP template for your organization (legal- or sales-heavy), or
• Provide a short vendor short-list tailored to your company size and industry.