Ollie AI Pricing 2026

Ollie AI is a freemium productivity tool that offers 6 key features including Works over plain SMS — no app, no login, no account, School email triage for permission slips and schedule changes, Shared family calendar with conflict and double-booking detection. Ollie AI is a family assistant that runs entirely over text message — no app to install, no account to create, no login. You text it, and it connects your calendars, email and to-do lists and texts back only what matters. The product is aimed squarely at the household default parent: the person who is the family's scheduler, reminder service and logistics coordinator by accident. Its most specific feature is school email triage, catching permission-slip deadlines, schedule changes and action items buried in mailing-list traffic that nobody reads in full. Alongside that it runs a shared family calendar that flags conflicts and double-bookings before they happen, and works as a capture inbox — the moment you think of something, you text it and let go. Ollie is proactive rather than purely reactive: it surfaces things that need attention and takes the next step rather than waiting to be asked. The privacy posture is stated up front, which matters for a tool holding a family's logistics: data is never sold or shared, it is not used to train models, email and calendar connect through delegated access so Ollie never sees a password, and the vendor says SOC 2 Type 1 certification is in progress. One subscription covers the whole family group chat.

✅ Ollie AI is a good choice if you need:

• •Works over plain SMS — no app, no login, no account
• •School email triage for permission slips and schedule changes
• •Shared family calendar with conflict and double-booking detection
• •Proactive follow-through rather than reactive question answering
• •One subscription covers the entire family group chat

💡 Value Assessment

With a free tier available, Ollie AI is an easy recommendation for anyone looking to try productivity tools without financial commitment. The paid plans offer good value for power users who need the additional features and higher usage limits.