Your OLL.E questions, answered
OLL.E (said "Ollie", a nod to Wall-E) is an AI watchman app for Android, iPhone and the web, made by OLL.E, Inc. You tell it in plain words what matters, for example "call me when a lead emails about pricing" or "wake me if a client messages after 10pm". It watches your phone notifications, Gmail, Upwork and Google Calendar around the clock. When that thing happens it calls you or sounds an alarm; everything less urgent waits in a silent Shortlist. It is not "Olle - AI Toolbar Assistant", which is a different product.
Yes. Connect Gmail, then type the watch: "Call me when Dane emails about the investment files", or "alarm me when any email from acme.com mentions an invoice". When a matching email lands, your phone rings with a real call and OLL.E sends a short brief of what the email says. Gmail's own settings can only turn notifications on or off per label; they can't ring you for one sender or one subject.
Yes, for Gmail, Upwork and Google Calendar: those watches work on iPhone with nothing extra, and a phone call rings like any other call. What iPhone does not allow is an app reading other apps' notifications in the background, so to watch WhatsApp, Slack, Telegram or Fiverr messages on iPhone you need OLL.E PinG, a keyring that relays those notifications and plays the alarm on its own speaker.
A phone call is the loudest thing a phone can do, and both Android and iPhone let you choose which callers and apps get through Do Not Disturb. Allow OLL.E there (on iPhone: Settings, Focus, then People and Apps; on newer Android: Settings, Modes, Notification filters) and urgent watches ring at night while the Shortlist stays silent. PinG rings on its own speaker, so it does not depend on the phone's sound settings at all.
Today: any app that sends notifications to your phone (WhatsApp, Messenger, SMS, Slack, Discord, Telegram, Fiverr and the rest), your Gmail inbox, new jobs on Upwork, and Google Calendar events, changes and cancellations. On Android, app notifications work out of the box; on iPhone they need PinG. Coming next: HubSpot, Notion, GitHub, flight prices, websites and MCP servers. We list a source here only once it is live.
Yes, with one limit that applies to every iPhone app. Gmail, Upwork and Calendar watches work fully, including phone-call alerts. Watching messages from other apps (WhatsApp, Slack, Fiverr, SMS) needs OLL.E PinG, because iOS does not let any app read notifications in the background. PinG pairs over Bluetooth, relays the notification stream to OLL.E, and rings loud enough to hear from the next room.
For building multi-step workflows between business apps, no: use Zapier, Make or n8n for that. For the one job many people use those tools for, "tell me the moment X happens", yes, with less setup. There is no flow to build: you type the sentence, OLL.E works out what counts as a match, and the alert is a phone call or an alarm rather than one more notification. IFTTT's phone-call service was the closest thing; OLL.E also reads the content, so "a client asking about pricing" is a match and a newsletter is not.
Yes, both. When a watch matches a client's message (WhatsApp, SMS, Slack, Fiverr and the rest), OLL.E can reply straight away with text you approved, or with a short reply written to fit what they said, before you have picked up the phone. On Android the reply is sent for you; on iPhone, apps cannot act inside other apps, so it waits as a draft you send with one tap. Email replies work the same on both: OLL.E can answer a client's email for you, forward it to anyone, label it, or summarise a long thread into a short brief. Nothing goes out unless you set it up in a watch.
Three things. It can call or alarm you a set time before a meeting ("call me 10 minutes before any client meeting"). It tells you when an event is added, moved or cancelled, which the normal calendar reminder never rings for. And it can create events for you from an email or message, for example holding the slot a client proposed while it drafts the reply confirming it.
It calls you, and before you pick up it has already started on the job: it writes the bid letter from the job post and your profile, finds the client's name, and sends you a short brief of what the client wants. It can also forward the job to anyone you choose, such as a teammate or your agency's bidder, so the right person sees it first. You set the filter in plain words, for example "Call me when an SEO job over $500 from a US client posts on Upwork". Sending the bid is always yours.
Upwork's own alerts are emails and app badges for every job in a saved search, and they look like everything else on your phone. OLL.E watches new Upwork jobs by your filter (skill, budget, client country) and phones you for the ones that match, then drafts the bid. Upwork X-Ray is our free sister site: it answers questions from 1.5 million Upwork jobs (when clients post, what they really pay, who actually hires) and sends free Telegram job alerts. Use X-Ray to decide what to watch; use OLL.E to be called when it posts.
The free plan stays free: 4 active watches, 10 alerts and 10 actions a month, no card needed. Pro is $19.99 a month (25 watches, 300 alerts, 300 actions) and Max is $79.99 a month (unlimited, with the stronger reasoning models). Yearly billing saves 20%. New accounts start with a 7-day free trial. PinG is sold separately as a one-time reservation.
It reads only what a watch you wrote needs in order to decide match or no match, and it keeps none of it: we do not store the content of your messages or emails, and nothing you connect is used to train AI models. Connections use the official Google and Apple permissions and are encrypted in transit and at rest. You can disconnect any source, or delete your account, from inside the app. The full detail is in the Privacy Policy.