AI Strategy When You're the Only Executive: A Small Company CEO's Playbook

Employees inputting sensitive B2B client data or proprietary company information into public AI models that train on user data.

Enforce the 1-page AI policy, and ensure you purchase 'Team' or 'Enterprise' tiers of AI tools (like ChatGPT Team) which explicitly state they do not train models on your workspace data.

Shadow IT and tool sprawl: Employees expensing multiple unvetted $20/mo AI subscriptions, quickly blowing past the $500/mo budget.

Centralize all AI purchasing through you or your finance lead. Mandate that employees must use the officially sanctioned tools from the pilot.

Low adoption rates post-training because employees feel intimidated by 'prompt engineering' or revert to old habits.

Provide a shared library of pre-written, fill-in-the-blank prompts specific to your company's back-office tasks so employees don't have to start from scratch.