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 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.

Whether SMB or enterprise, start with one team and one workflow. A support team using your ticket agent, a sales team using your research agent, one department automating one process. Prove ROI in a contained scope before expanding.

Expansion revenue (existing customers buying more seats, workflows, or integrations) is cheaper and faster than new customer acquisition. Build expansion into your product: usage dashboards that show ROI, easy seat addition, and workflow templates that suggest the next automation.

The land-and-expand playbook: Month 1-3, one team, one workflow, prove ROI. Month 4-6, add seats and adjacent workflows. Month 7-12, expand to additional departments with the original champion as internal champion. Year 2, enterprise-wide rollout with the ROI data from Year 1 as the internal sales pitch.