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Ollie AI

Text-message family assistant — catches school-email deadlines, runs the shared calendar

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freemiumThree published tiers metered on messages Ollie sends back to you, plus a daily free allowance on every plan that is consumed before the monthly pool and does not roll over. Free is $0 and includes 50 messages from Ollie per month plus 6 free additional messages every day, with no credit card or account needed to start. Everyday — marked most popular — is $25 per month for 150 monthly messages plus 10 free daily messages, and one subscription covers the whole family group chat. Always-On is $100 per month for 1,000 monthly messages plus 15 free daily messages, also covering the full family. Monthly messages do not accumulate or roll over. Top-ups are available on the paid tiers at $0.30 per message on Everyday and $0.25 per message on Always-On. Upgrade, downgrade or cancel by texting Ollie.View full pricing →

About Ollie AI

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.

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Key Features

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
Delegated email and calendar access — no password stored

Ollie AI Pros & Cons

Pros

  • +Zero-install SMS delivery removes the adoption problem family apps always hit
  • +Privacy terms are specific and stated on the marketing page, not buried
  • +Household-wide coverage on one seat rather than per-person pricing

⚠️ Cons

  • Message metering is tight and unused messages expire monthly
  • SOC 2 is only in progress, not certified
  • Top-ups are per-message, which makes heavy months expensive to predict

Tags

ai-assistantfamilysmscalendaremail-triagereminders
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