You forgot. Oscar didn't.
A proactive AI assistant that manages your calendar, triages your email, tracks your commitments, and represents you in online communities — all without you asking.
$49/mo add-on. Available on Pro, Master, and Elite plans. 90-day money-back guarantee.
Three steps. Then Oscar runs.
No complicated setup, no workflow redesign. Connect your tools once and Oscar handles the rest in the background.
Enable Oscar VA
Add Oscar VA to your Pro or higher plan. Takes 30 seconds. No separate app, no new dashboard — he lives in the same OSQR interface you already use.
Connect your tools
Link your Google Calendar, Gmail or IMAP inbox, and optionally add a phone line. OAuth for Google, encrypted credentials for IMAP. Oscar never stores passwords in plain text.
Oscar takes over
Morning briefs start automatically. Reminders fire before meetings. Inbox summaries land in SMS. Commitments get tracked. You just respond to what surfaces.
Every surface of your work day.
Calendar, email, commitments, community — Oscar handles the coordination layer so you can focus on the work that actually requires you.
Calendar Intelligence
Oscar reads your upcoming events and surfaces what you need to prepare — not just what time it starts. Know your day before it starts.
Email Triage
Works with Gmail and any IMAP provider. Oscar reads your inbox, surfaces what matters, and summarizes overnight threads so you start every day caught up.
Commitment Tracking
"You said you'd follow up with Sarah last Thursday." Oscar catches the follow-ups you forget, the promises buried in threads, and the deadlines you agreed to in passing.
Morning Briefs
Get a personalized SMS brief every morning — calendar, email highlights, open commitments, and anything worth your attention. Ready before your first coffee.
Meeting Notes
Paste in a transcript or let Oscar monitor your calendar. He generates structured notes, action items, and follow-up drafts — so you actually use what was decided.
Community Presence
Oscar monitors HN, Reddit, Dev.to, Indie Hackers, and LinkedIn for relevant threads. He drafts a response in your voice. You approve via SMS before anything posts.
SMS Gateway
Two-way SMS with Oscar, proactive alerts when something needs your attention, and outbound messaging on your behalf. He texts you — not the other way around.
Dedicated Phone Line
Optional $10/mo add-on. A real phone number for Oscar — inbound VA calls, outbound messaging, and the full SMS workflow tied to a number that's yours.
Real scenarios. Real workflows.
Oscar doesn't wait for you to ask. He watches, remembers, and acts — so nothing falls through the cracks.
Your morning runs itself
You wake up to a text from Oscar: “3 things today.” Your morning brief pulls from your calendar, email, tracked commitments, and market data — then composes it into one message. Jesse still hasn't sent those foundation plans (2 days overdue). You have a site walk at 2pm. Lumber prices dropped 8% on your Pine Valley project. You didn't ask for any of it. Oscar just knows what matters and tells you before you open the app.
“Watch for this” — and Oscar does
You tell Oscar: “When Jesse emails me anything, text me right away.” That's it. Three days later, Jesse's email arrives at 9pm. Oscar fires a text: “Jesse sent you revised foundation plans. Want me to pull up the attachment?” You reply “yes” from your couch. Standing directives run continuously — email triggers, schedule triggers, event triggers — with safety rails and a $2/day cost ceiling.
Nothing falls through the cracks
During a call you mention: “The city inspector is coming Friday.” Oscar silently tracks that commitment. Thursday evening, it nudges you: “Inspector visit tomorrow — need to prep anything?” You also told Oscar that Mike owes you the electrical rough-in schedule by end of week. When Friday passes with no email, Oscar follows up automatically: “Hey Mike, just checking in on that rough-in schedule.” You didn't lift a finger.
Background Research
“Research what the IRC says about egress windows for basement bedrooms and text me back.” Oscar queues the task, runs multi-tool research asynchronously — web search, your vault, URL fetching — and delivers results via SMS. You close the app. Three minutes later, your phone buzzes with the answer. Oscar works while you don't.
Oscar knows your work
Siri sets timers. Alexa plays music. Oscar knows the 47 documents in your Knowledge Vault, the three projects you're actively juggling, the communication style you use with different clients, and the commitments buried in your email from last week.
He doesn't wait to be asked. He surfaces what matters, flags what's falling through the cracks, and drafts responses that sound like you — because he's learned from everything you've told him.
Enable Oscar VASimple add-on pricing
Oscar VA is an add-on to any Pro or higher plan. No seat fees, no per-SMS charges on standard usage.
Oscar VA
Full virtual assistant capabilities
- Morning briefs from 7 data sources via SMS
- Standing Directives — "if X, then Oscar"
- Background research — async tasks, SMS delivery
- Commitment tracking with auto follow-up
- Calendar intelligence and meeting prep
- Gmail + IMAP email triage
- Community Presence (HN, Reddit, Dev.to, LinkedIn)
- Two-way SMS with Oscar
Requires Pro plan ($79/mo) or higher
Dedicated Phone Line
Optional add-on for inbound/outbound calling
- A dedicated phone number for Oscar
- Inbound VA calls routed to Oscar
- Outbound SMS on your behalf
- Full two-way SMS workflow
- Number tied to your account permanently
- Requires Oscar VA ($49/mo)
Add-on to Oscar VA
Oscar VA is one part of OSQR
The same subscription gives you multi-model AI reasoning across Claude, GPT-4o, Gemini, and Grok — a private knowledge vault for all your documents, construction estimating from blueprints, social media publishing, and conversation memory across months. Oscar VA is how people get started. Then they use everything else.
Ready to stop dropping balls?
Enable Oscar VA and wake up tomorrow with your calendar prepped, your inbox triaged, and the commitment you almost forgot — already drafted as a follow-up.