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ClickUp vs Raycast AI

A feature-by-feature comparison of ClickUp and Raycast AI across 7 capability categories.

First tool

Try ClickUp (opens in a new tab)

Second tool

Try Raycast AI (opens in a new tab)

Modalities — Tie

Modalities: ClickUp compared with Raycast AI
Feature	ClickUp	Raycast AI
Text Input	Yes, requires free plan. Chat, docs, tasks, and Brain² take natural language. Free forever is advertised.	Yes, requires pro plan. AI chat in the Raycast launcher accepts text prompts.
Image Upload / Vision	Unknown. Whiteboards/clips exist. Vision on Brain² was not specified.	Partial. Screen capture and file context. General image upload was not separately documented.
Image Generation	No. You can attach images. ClickUp is not an image model.	Unknown. Whether image gen models are in the 32+ model list was not checked.
Voice Mode	Unknown. AI Notetaker and voice notes are named. A two-way voice loop was not documented.	Unknown. Voice input was not confirmed on the AI page.
Video Understanding	Unknown. Clips exist. Video-as-vision was not specified.	No. Not a video analysis product.
Video Generation	No. Not a video generation product.	No. Not a video generation product.
File Upload (PDF, DOCX)	Yes, requires free plan. Docs, attachments, and connected Drive/GitHub.	Yes, requires pro plan. PDF, CSV, and file context in AI chat.
Code Execution	Partial. Codegen Agent is advertised. That is agent code, not a user Python sandbox in chat.	Unknown. Whether AI runs code locally was not confirmed.
Audio Input	Partial. AI Notetaker and PRD-from-voice-notes are advertised.	Unknown. Speech input was not checked.
Canvas / Artifact Editor	Unknown. Overlapping columns disagreed (yes vs partial); left unverified rather than copying a no.	Unknown. Overlapping columns disagreed (no vs partial); left unverified rather than copying a no.
Screen Sharing / Computer Use	No. No computer-use desktop takeover.	Partial. Screen context for AI queries. Not live screen sharing to others.

Memory & Context — ClickUp Wins

Memory & Context: ClickUp compared with Raycast AI
Feature	ClickUp	Raycast AI
Persistent Memory	Yes, requires free plan. Brain²: infinite memory of tasks, docs, tone, and preferences. Multiplayer AI shares team context.	Partial. Chat history in Raycast. No cross-device cloud memory advertised.
Large Context Window	Unknown. No token window is published. Brain² “picks the best model”.	Unknown. Depends on the selected model (32+ providers).
Custom Instructions	Yes, requires free plan. Personality, sprint methods, and preference memory are the instruction layer.	Partial. Extensions and prompts customize behavior. No global system profile documented.
Conversation History	Yes, requires free plan. Chat, comments, and docs persist.	Yes, requires pro plan. AI chat history persists in Raycast.

Integrations — ClickUp Wins

Integrations: ClickUp compared with Raycast AI
Feature	ClickUp	Raycast AI
Web Search / Browsing	Yes, requires plus plan. Brain² “checks your workspace, apps, and the web.”	Yes, requires pro plan. Web search with inline references in AI chat.
Plugins / Extensions	Yes, requires free plan. 100+ products, GitHub/Figma/Salesforce, MCP, automations.	Yes, requires pro plan. Raycast extensions and AI Extensions ecosystem.
API Access	Yes, requires plus plan. API calls are listed among product capabilities.	No. Consumer launcher, not a public inference API.
Zapier Integration	Unknown. Integrations exist. A first-party Zapier listing was not checked.	Unknown. Zapier was not checked.
Custom GPTs / Bots	Yes, requires free plan. Build your own agent; Super Agent 24/7.	Partial. Custom AI Extensions act like specialized bots.
Real-time Collaboration	Yes, requires free plan. Multiplayer AI and shared workspace.	No. Single-user launcher.
Live Social Data Integration	No. No live social firehose.	No. No social firehose.
Live Citation Mapping	No. Not a cited-search product.	Partial. Web search shows inline reference links.

Developer — Raycast AI Wins

Developer: ClickUp compared with Raycast AI
Feature	ClickUp	Raycast AI
Function Calling	Yes, requires free plan. Agents with 500+ tool superpowers and MCP.	Yes, requires pro plan. AI Extensions invoke app actions and tools.
Streaming Responses	Unknown. Not specified on the homepage.	Yes, requires pro plan. AI responses stream in the launcher.
Fine-Tuning	No. Uses GPT/Claude/Gemini. ClickUp does not train those weights.	No. Routes to third-party models; does not fine-tune.
Embeddings API	No. Not an embeddings vendor.	No. Not an embeddings product.
Structured Output (JSON)	Partial. Tasks, custom fields, dashboards. Not JSON-schema chat.	Unknown. JSON mode depends on the selected model.
Reasoning / Thinking Mode	Partial. Brain² picks frontier models. Not a user Deep Think toggle.	Unknown. Overlapping columns disagreed (yes vs partial); left unverified rather than copying a no.
Local Execution	No. Cloud SaaS.	Yes, requires pro plan. Ollama local models run on-device.
Open Weights	No. Closed product wrapping frontier APIs.	Partial. Ollama routes to open-weight local models.
Multi-Agent Orchestration	Yes, requires plus plan. Intake, Assign, PM, Live Answers agents and more.	No. Single chat session, not multi-agent.

Platforms — ClickUp Wins

Platforms: ClickUp compared with Raycast AI
Feature	ClickUp	Raycast AI
Web App	Yes, requires free plan. clickup.com.	No. Native macOS app, not a web chat.
iOS App	Yes, requires free plan. Native iOS listed.	No. No iOS app for Raycast AI.
Android App	Yes, requires free plan. Native Android listed.	No. No Android app.
Desktop App	Yes, requires free plan. macOS and Windows listed.	Yes, requires pro plan. Raycast is a macOS desktop launcher with built-in AI.
Chrome Extension	Unknown. Not confirmed on the homepage.	No. No Chrome extension.

Privacy — ClickUp Wins

Privacy: ClickUp compared with Raycast AI
Feature	ClickUp	Raycast AI
GDPR Compliant	Unknown. SOC 2 Type II is claimed. A GDPR statement was not isolated on the homepage.	Unknown. Privacy policy was not re-read.
Opt Out of Data Training	Yes, requires free plan. Homepage: agreements ensure zero data training and retention on all third-party model providers.	Yes, requires pro plan. Raycast states it does not train on your data.
Enterprise Privacy Mode	Yes, requires enterprise plan. SSO, SOC 2 Type II, 24/7 support. Seat dollars were not extracted.	Partial. Team plans exist. Enterprise DPA not read.

Workspaces — ClickUp Wins

Workspaces: ClickUp compared with Raycast AI
Feature	ClickUp	Raycast AI
Projects / Folders	Yes, requires free plan. Spaces, folders, lists, and projects.	Partial. Extensions and snippets organize workflows, not chat project folders.