Short verdict
Ooma Office is generally the stronger small-business phone foundation. Grasshopper is simpler and cheaper-feeling for solo owners, but lighter for complex AI receptionist workflows.
Decision matrix
Implementation take
The winning choice depends less on the logo and more on where the AI receptionist will sit in the call flow. Native AI can be faster when the provider already owns the number and routing rules. External AI can be more flexible when the business needs custom scripts, multi-system handoff, or a separate voice-agent platform.