Cortex · the trust layer
Five kinds of evidence. One answer you can check.
Before it writes a word, Cortex searches everything your company knows, reads the original pages when the index isn't enough, and shows every source it used, so you can check the answer yourself.
Files
Contracts, decks, sheets and scans from your Mac, Google Drive and Notion, searched by meaning. When a table or a layout matters, Cortex reads the original page.
Mail & calendar
Gmail threads and calendar entries, kept current as they change.
Memory
People, accounts and decisions it has learned from your conversations, kept as memory and wiki pages.
Conversations
Earlier chats come back when they matter, so you never explain the same thing twice.
Knowledge Packs
Your team's playbooks, handbooks and pricing rules, cited like any document.
The guard
Every source is marked Strong or Relevant. An answer may cite only what Cortex read, and a claim that something is missing or complete is checked. When nothing supports an answer, Cortex says so.
Assistant
Walk into every meeting prepared.
Press Prepare on a meeting. OverShoulder reads your mail with everyone coming, what your Cortex holds on the account, and the company's public pages, then lists what matters, with a source under every point.
Drawn from the app's own screens · the meeting brief
Council
Big decision? Get a second, third and fourth opinion.
Type /council in any chat, choose the models and the one that moderates, then ask. Council researches the question in your Cortex and on the web. Every model answers on its own, the moderator writes an interim result, and the others push back until they agree. You see every round.
Drawn from the app's own screens · a Council tab
Active Guide
Stuck in an app? It tells you the next step.
Share your screen when you choose. Active Guide reads the page you are on, tells you the next click in plain words, and waits until you pause before it gives the step after that. It knows the tools you open twice a year.
Drawn from the app's own screens · the pages on the left are stand-ins, labelled as each vendor's help pages name them
Security
Private by design.
Eight protections, on from the first launch. Your index stays on your Mac, Central keeps nothing once a request ends, and you choose what a model may see.
- Read-only, and no mail sent for you: Google Drive and Gmail connect read-only. Calendar is written only when you add an event, so no invitation goes out. OverShoulder never sends an email.
- Your index stays on your Mac: Cortex keeps its index of your files, your memory and your privacy log in a database on your Mac. To index a file, it sends the file’s text to Google’s models through OverShoulder Central.
- Keys sealed by your Mac: Connector tokens, your own API keys and your chat history are encrypted with AES-256-GCM under a key sealed in the macOS Keychain.
- Pages masked in your browser: Browser Reader masks emails, phone, card and ID numbers, passwords and keys before a page’s text leaves your browser. Screen sharing starts only when you press Share.
- You choose what the AI may see: Strict replaces the people, companies, amounts and dates in your memory with aliases. Balanced, the default, holds back personal fields such as phone numbers and addresses.
- Nothing kept in the middle: Requests go over TLS to OverShoulder Central and on to the AI provider. Central keeps no prompt, context, screen or answer once a request finishes. A Knowledge Pack you share stays until you delete it.
- Never used for training: OverShoulder does not use your content to train AI models.
- See what your memory shared: The Privacy tab lists the AI calls of the last 30 days that drew on your memory, and the provider each went to. It records no message text.
Every detail is in the Privacy Policy.
- What is OverShoulder?
- A Mac app that reads your company's files, mail, calendar and team knowledge, and answers your questions with the sources it used. It also prepares your meetings, puts big decisions to a council of models, and guides you through apps step by step.
- Where is my data kept?
- Your Cortex index, memory and privacy log stay on your Mac. Requests pass through OverShoulder Central, on Google Cloud in the United States, which keeps no prompt, context or answer once a request finishes. Knowledge Packs you share are stored there until you delete them.
- Which AI models can I use?
- Claude, GPT and Gemini, from Anthropic, OpenAI and Google, from fast to the most capable. Council uses three at once.
- What does it cost?
- You pay in credits: one credit is $0.01, and a chat costs from one credit, depending on the model. A new account gets 300 credits for 7 days, and credits come in packs of 1,000, 3,000 and 6,000.
- Does it send email for me?
- No. Gmail is connected read-only. OverShoulder can draft a reply when you ask, and you send it yourself.
- Can my team share what it knows?
- Yes, with Knowledge Packs: documents your team can ask about. Share a pack with a code, and answers cite its documents like any file.
- Can I delete my data?
- Yes. Delete a folder's index in Cortex (your files stay where they are), and clear memories and chat history in the app. To delete your account, write to support@overshoulder.ai.
- Do you train AI on my data?
- No. OverShoulder does not use your content to train AI models.
- Is there a Windows version?
- Not yet. The beta runs on Macs, with Apple silicon or Intel, on macOS 13 or later.
Feedback
Tell us what to build next.
Every answer in the app has a thumbs up and a thumbs down, and those ratings come straight to the team. For anything longer, write here: we read every message.
