Sam Lessin: software sales now means selling to executives or selling to LLMs

lessin · x · 2026-09-05

Sam Lessin argues the SaaS playbook — cheap per-seat subscriptions spread by human word of mouth — is dead: 'people don't buy from people anymore.' Going forward there are only two paths: real enterprise sales of very expensive, lock-in solutions to leadership (a common mistake: doing the sales work but not charging enough), or LLM-based sales, since he now often just lets an LLM pick his software. Consumers are the exception: amid a sea of AI fakes, human trust and word of mouth matter more for consumer goods — but for tech, machines are already buying from machines.

Related event: Debate: will enterprise software sell to execs, LLMs, or digital coworkers(3 posts)→

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