Ollie

Ollie is an AI family assistant that runs over text message, managing calendars, school emails, meals and errands for busy parents. There is no app to download: you text Ollie like you would a person, and it reads your connected calendars and email, flags what matters, and handles tasks. Its main difference from household planners is that it acts, from booking a grooming appointment to placing a grocery order or paying a bill.

What is Ollie used for?

Families use Ollie to offload the daily coordination and admin that usually falls on one person.

• Receiving a daily briefing that pulls from calendars, email and to-dos
• Spotting schedule changes in school emails and apps, then offering to add them to the calendar
• Adding events and reminders, or reorganizing a busy month around a trip
• Booking appointments, filling in forms, placing orders on Amazon, Walmart or Instacart, and paying bills
• Canceling unwanted subscriptions through the account settings
• Planning weekly meals by swiping a personalized menu, then ordering a combined, aisle-sorted grocery list

Who Ollie is best for

Ollie suits working parents with packed schedules, households where several people need to stay in sync, and anyone who prefers texting to opening another app. Families who are uncomfortable giving an assistant delegated access to email, calendars and payment accounts, or who only need a shared calendar, may be better served by simpler tools.

Ollie pricing

Ollie has a free plan with 50 messages from Ollie per month plus 6 free messages each day. As of October 2026 the Everyday plan costs $25 per month for 150 monthly messages plus 10 free daily messages, and the Always-On plan costs $100 per month for 1,000 monthly messages plus 15 free daily messages. Both paid plans cover the whole family group chat. A message is one reply from Ollie, and unused messages do not roll over. Top-ups cost $0.30 per message on Everyday and $0.25 on Always-On.

Limitations to keep in mind

• Every plan has message limits, and complex requests can use more than one message
• Account actions such as bill pay depend on Ollie navigating third-party websites correctly
• Delegated access to email and calendars is a meaningful privacy decision
• Text-only interaction is less suited to browsing a whole month at a glance

Ollie vs alternatives

Image to Calendar does one thing, turning a flyer or timetable into calendar events, and is enough if scanning dates is your main need. Motion and Reclaim AI auto-schedule work tasks and meetings for professionals rather than families. ChatGPT can draft a meal plan or summarize a school email when you paste it in, but it does not watch your inbox or place orders for you. Ollie wins when you want an assistant that proactively monitors family logistics and completes errands over text.

Tips for getting started with Ollie

Connect your main calendar and email first, then add your partner to the family group chat so one subscription covers you both. Ask how you are tracking on messages during the first week to understand how many you really use. Start with low-risk actions like reminders and grocery lists before handing over bill payments. Be specific in requests, for example naming the store and delivery window, to avoid extra back-and-forth messages.

Ollie FAQ

Is Ollie free?

Yes. Ollie has a free plan with 50 messages per month plus 6 free daily messages, and paid plans start at $25 per month as of October 2026.

Do I need to download an app to use Ollie?

No. Ollie works entirely over text message, with no app or login required, and connects to your calendars and email through delegated access.

Is Ollie safe to use with my email and accounts?

Ollie is SOC 2 Type 1 compliant, says it never sells your data or uses it to train AI models, and does not see or store your email password.

What is the best alternative to Ollie?

Image to Calendar suits people who only need to turn flyers into events, and Motion is better for AI scheduling of work tasks.