What should I ask a vendor before committing to an e-signature plan?

Before committing to an e-signature plan, ask questions in five areas: fit, security/compliance, workflow/integrations, pricing/contract, and support/exit strategy.

1) Fit for your use case

• What document types and signing workflows do you support?
• Can you handle simple signatures, multi-party routing, sequential signing, and approvals?
• Do you support templates, reusable fields, and bulk sending?
• Can signers be internal, external, or both?
• Is there a signing portal or is everything email-based?
• How does the signer experience work on mobile and desktop?

2) Security and compliance

• What compliance standards do you meet?
  • e.g., eIDAS, ESIGN/UETA, SOC 2, ISO 27001, HIPAA, GDPR, etc.
• Are audit trails included with every envelope/document?
• How do you verify signer identity?
• Are signatures legally enforceable in the regions where we operate?
• Where is data stored, and can you offer data residency options?
• What encryption do you use at rest and in transit?
• How do you handle access controls, SSO, MFA, and role-based permissions?
• Do you support document retention policies and legal holds?

3) Workflow and integrations

• Which systems do you integrate with natively?
  • e.g., CRM, ERP, HRIS, cloud storage, identity providers
• Do you have an API, and what are its limits?
• Can we automate sending, reminders, and status updates?
• Can signed documents be automatically routed to our systems?
• Do you support custom branding and email domains?
• Can we embed signing into our own app or website?
• How easy is it to build and maintain workflows without heavy admin support?

4) Pricing and contract terms

• What exactly is included in each plan?
• Are signatures charged per user, per document, per envelope, or per seat?
• Are there overage fees, API fees, storage fees, or support fees?
• What counts as a “transaction”?
• Is there a minimum commitment or annual contract?
• What happens if we exceed usage?
• Are templates, API access, branding, and advanced security features extra?
• How often do prices increase, and what notice do you give?
• What is the cancellation policy and renewal term?

5) Support, reliability, and exit strategy

• What support levels are included? Is support 24/7?
• What are your SLA and uptime commitments?
• How fast do you respond to critical issues?
• Do you provide onboarding and migration help?
• Can we export all documents, audit logs, and metadata if we leave?
• What happens to our data after termination?
• Do you have references from customers in our industry?
• Can we do a pilot or trial with real workflows before signing?

Good “must-ask” questions

If you want the shortest list, ask these:

1. What’s included in the base price, and what costs extra?
2. Do you support our required compliance/security standards?
3. Can it integrate with our core systems and workflows?
4. Is the signer experience simple for external users?
5. Can we export everything and leave cleanly if needed?
6. What support and SLA do we get?

If you want, I can also turn this into a vendor evaluation checklist or a scorecard template you can use in demos.