How to Get SMBs to Pay for AI Tools

June 25, 2026

The number of SMBs paying for AI tools varies dramatically by headcount, from 57% of those with fewer than 20 employees to 93% of those with 100 to 1,000 employees. Our recent survey of 500 U.S. decision-makers explores why some SMBs stick with free tools and what works to convert them to paying customers.

The top reason SMBs stick with free AI tools, by headcount:

  • Very small businesses (VSBs, 1–19 employees): The free version does everything they need
  • Small businesses (SBs, 20–99 employees): The free version does everything they need, followed by "plan to upgrade but haven't gotten around to it"
  • Midsized businesses (MBs, 100–1,000 employees): The free version does everything they need, tied with “plan to upgrade but haven't gotten around to it”

What would convince SMBs to pay for AI tools, by headcount:

  • VSBs: Clear examples of payback, tied with a lower price point
  • SBs and MBs: Clear examples of payback, followed by guidance on using advanced features

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