Glean vs sideOS
Glean and sideOS are both AI assistants tools. Glean is aimed at enterprise, while sideOS is aimed at freelancers and developers.
Enterprise AI search and assistant across all your company apps
Voice-driven Mac agent in the notch with local dictation and meetings
| Pricing | Paid | Paid |
| Starting price | Not published | Not published |
| Free plan | No | No |
| Free trial | — | — |
| Built for | Enterprise | Freelancers, Developers, Small businesses |
| Platforms | web | macos |
| Country | US · 2019 | — |
| Rating | — | — |
Choose Glean if
Large companies with knowledge spread across dozens of SaaS tools that need permission-safe AI search and assistants.
- Among the most mature permission-aware enterprise search products
- Very broad connector library including code and ticketing tools
- Model-agnostic, so companies are not tied to one AI vendor
Look elsewhere if: Small teams or firms already standardized on one suite's AI (Microsoft 365 Copilot, ChatGPT Enterprise or Notion AI are simpler).
Choose sideOS if
Mac professionals who want a private voice agent, dictation and meeting notes in one app they pay for once.
- One-time licence with all future updates and no subscription
- No account and no sideOS server between you and the model
- Dictation and meeting transcription stay on the Mac
Look elsewhere if: Windows or mobile users and teams that need shared meeting notes or admin controls (Granola, Raycast).
Glean vs sideOS pricing
Glean
- EnterpriseCustom quoteSales-led, seat-based; Search, Assistant and Agents via demo
sideOS
- Lifetime licence$89.90One-time; one Mac at a time, every future update included
- AI model usageVariesPaid to your own provider, about 2 to 5 cents per command
Glean · Key features
- Permission-aware enterprise search across 275+ connected apps
- Glean Assistant answers questions with citations to company sources
- Glean Agents that automate multi-step tasks from plain-language instructions
- Enterprise Graph mapping people, content, projects and activity
- Near real-time permission sync so users only see what they may access
- Model routing across 40+ open and frontier models
Cons
- No public pricing and no self-serve trial
- Priced for enterprises; reported seat minimums put off small firms
- Answer quality depends on tidy permissions and content in sources
sideOS · Key features
- Hold-to-talk agent that reads the screen, clicks, types and runs AppleScript
- On-device dictation into any app in 62 languages at no extra cost
- Meeting recording for Zoom, Meet and Teams with on-device Whisper and speakers
- Background tasks with web search, file access and approved shell commands
- Reminders that can complete a task before they fire
- One-click MCP connections for Gmail, Calendar, Notion, Slack and GitHub
Cons
- Apple Silicon Macs with macOS 14 or later only
- Agent use adds API costs unless you run a local model
- No free trial or refund window stated on the site
Glean vs sideOS: FAQ
Do Glean and sideOS have a free plan?
Glean has no free plan. sideOS has no free plan.
Which is better for small businesses, Glean or sideOS?
sideOS lists small businesses as a core audience, while Glean is aimed more at enterprise.