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Go-to-Market3 min readReviewed Aug 2026

Selling Agents to SMB vs. Enterprise

Self-serve vs. sales-led motion, security questionnaires, and procurement timelines.

SMB motion

SMB sales (companies under 200 employees) should be self-serve: Stripe checkout, 14-day trial or freemium tier, template onboarding, and email/Loom support. Decision cycle: 1-7 days. ACV: $500-5,000/year.

The SMB buyer is usually the user - not a support manager, but a founder who feels the pain directly. They do not need a security review, legal approval, or procurement process. They need to see value in the first session and hit 'first win' within 7 days.

Optimize for time-to-value: pre-built integrations, sample data, guided setup wizard, and a 'first task in 5 minutes' onboarding flow. SMB customers who do not complete a successful task their first week churn at 3x the rate of those who do.

Enterprise motion

Enterprise sales (500+ employees) requires a sales-led motion: outbound to champions, demo to stakeholders, security questionnaire, DPA negotiation, pilot proposal, and procurement. Decision cycle: 3-9 months. ACV: $25,000-250,000/year.

You need three contacts: a champion (daily user who loves the product), an economic buyer (VP/Director who controls budget), and an IT/security approver. Missing any one stalls the deal.

Do not pretend to be enterprise-ready without basics: SOC 2 Type II (or a roadmap with timeline), SSO/SAML, data processing agreement, audit logs, and role-based access controls. Enterprise buyers ask about these in the first call. 'We are working on SOC 2' with a specific timeline is acceptable. 'We will figure it out later' is not.

4 more sections in this article

  • Land and expand
  • The security review
  • Procurement and the paperwork
  • Pick one motion first

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Published 27 July 2026. Last reviewed 17 August 2026. We re-read this library on a schedule and date every article, so you can see for yourself how current it is.