Knowledge Base

Click the "Add to Slack" button on our homepage or any page on the site. This opens Slack's OAuth screen where you authorize Caddie for your workspace. You'll need workspace admin permissions, or your admin will need to approve the install.

Once installed, Caddie appears in your Slack sidebar under Apps. Click it to open a DM and start the setup process.

When you first message Caddie, you'll go through a quick guided setup:

1. Your website — Paste your company URL. Caddie scrapes it to understand your business, products, and ideal customer profile.
2. Your profile — Share your LinkedIn URL or describe your role. This helps Caddie personalize everything to your voice and responsibilities.
3. Pick your path — Choose "I know what I want to automate" to browse and select specific skills, or "Just exploring" to pick the platforms you use and get personalized recommendations.
4. Connect tools — Based on the skills you selected, Caddie shows which tools to connect (Gmail, HubSpot, LinkedIn, etc.). Click to authorize each one.
5. Try it live — Caddie runs your first skill immediately so you can see it in action (e.g., "Give me a topic and I'll draft your first LinkedIn post").
6. You're set up! — Onboarding is complete. You can browse and install more skills anytime.

The entire process takes about 2-3 minutes.

You need permission to install apps in your workspace. If your workspace requires admin approval for new apps, an admin will receive a request. Once approved, any member can use Caddie by messaging it directly.

Caddie offers a free tier to get started. Visit our pricing page for details on plans and features.

There are two ways to interact with Caddie:

• Direct message — Find Caddie under Apps in your Slack sidebar and click it to open a DM. This is the primary way to use Caddie.
• Mention in a thread — In any channel or group DM, mention @Caddie in a thread and Caddie will respond in that thread with context from the conversation.

You can talk to Caddie in plain English. Here are some examples:

• "Draft a LinkedIn post about our latest feature launch"
• "Check my email and tell me what's urgent"
• "Prep me for my 2pm meeting with Acme Corp"
• "Find Reddit threads where people are asking about [your product category]"
• "Follow up with the leads I haven't contacted in a week"
• "Research this company: [URL]"
• "Give me my morning roundup"
• "Sync my last call notes to HubSpot"

Caddie uses the tools you've connected and the skills you've installed to take real action — not just provide suggestions. It will draft emails, update your CRM, post content, and more, always with your approval before anything is sent.

Caddie streams responses in real time directly in Slack. Responses are formatted with Slack-native markdown (bold, lists, links, code blocks) for easy reading.

At the bottom of each response, you'll see feedback buttons (thumbs up / thumbs down). Use these to help Caddie learn your preferences — it will adjust future responses based on your feedback.

Caddie never sends external messages (emails, LinkedIn messages, posts) without your explicit approval. When Caddie drafts something, it shows you the draft in Slack first. You review, edit if needed, and confirm before anything is sent.

For scheduled skills (like Morning Roundup), Caddie will post summaries to your Slack DM at the scheduled time. These are internal messages to you — not external communications.

When you start a new conversation with Caddie, you'll see suggested prompts based on the tools you've connected and skills you've installed. For example, if you have Gmail connected, you might see "Check my email." These are shortcuts — you can always type your own request instead.

A skill is a pre-built workflow template that tells Caddie how to perform a specific task. Each skill has a name, required tools, and a step-by-step process. For example, the LinkedIn Ghostwriter skill knows how to research topics, draft posts in your voice, and publish them.

Browse all available skills on the Skills Library.

There are several ways to install a skill:

1. From the Skills Library — Visit caddieagent.ai/skills, find a skill, click it for details, and use the "Copy to Slack" button. Paste the install command into your Caddie DM.
2. By messaging Caddie — Type install [skill-name] in your DM with Caddie. For example: install linkedin-ghostwriter
3. From App Home — Open Caddie's App Home tab in Slack to see available and installed skills. Click Install on any skill.
4. During onboarding — You'll be prompted to pick skills as part of the setup flow.

Each skill lists its required tools (e.g., LinkedIn Ghostwriter needs Slack + LinkedIn). If you try to install a skill and a required tool isn't connected yet, Caddie will tell you which tools are missing and offer to help you connect them right there in the conversation.

Just ask Caddie in natural language. You don't need to memorize commands. Caddie matches your request to the right skill automatically.

Examples:

• LinkedIn Ghostwriter: "Draft a LinkedIn post about [topic]"
• Morning Roundup: "Give me my morning roundup"
• Meeting Prep: "Prep me for my next meeting"
• Reddit Scout: "Find Reddit threads about [topic]"
• Smart Follow-Ups: "Draft follow-ups for my stale deals"
• CRM Sync: "Sync my call notes to HubSpot"

Say remove [skill-name] in your DM with Caddie, or use the App Home tab to uninstall skills. Removing a skill doesn't disconnect any tools — it just removes that workflow from your Caddie.

Yes. Just describe what you want Caddie to do in plain English, and if it involves a regular workflow, Caddie will offer to save it as a custom skill. For example: "Every morning, check my email and Slack, then give me a summary of what needs my attention."

Caddie integrates with the following tools:

Visit the Integrations page for full details on each tool.

There are several ways:

1. Message Caddie: Type connect gmail (or any tool name) in your DM. Caddie will show an authorization button.
2. During onboarding: Tool connection buttons are shown automatically based on the skills you pick.
3. When Caddie needs a tool: If you ask Caddie to do something that requires a tool you haven't connected, it will prompt you to connect it.
4. From App Home: The App Home tab shows all available tools with Connect/Disconnect buttons.

When you click Connect, a browser window opens with the tool's standard OAuth authorization screen (e.g., Google's "Sign in with Google" page). Authorize access, and you'll be redirected back. Caddie confirms the connection in your Slack DM.

Caddie requests only the permissions needed for your installed skills. For example:

• Gmail: Read and send emails on your behalf
• Google Calendar: Read and create calendar events
• LinkedIn: Read your profile, messages, and post on your behalf
• HubSpot: Read and update contacts, deals, and activities
• Slack: Read messages in channels you're in, send messages as Caddie

Caddie never performs actions on connected tools without your explicit approval. All drafts are shown to you in Slack before being sent.

Open Caddie's App Home tab in Slack and click Disconnect next to the tool you want to remove. You can also say disconnect gmail in your DM. Disconnecting removes Caddie's access immediately. You can reconnect anytime.

No. Each user's tool connections are completely private. Your Gmail, CRM, LinkedIn, and other tool data is only accessible to your own Caddie instance. Workspace admins cannot see your connected tools or the data Caddie accesses on your behalf.

Caddie builds a personal profile (called skills.md) that improves over time through three methods:

1. Tell it directly: Say things like "Remember that I prefer short paragraphs" or "Always include a CTA in my LinkedIn posts." Caddie saves these as Custom Rules that apply to every future interaction.
2. Use feedback buttons: Thumbs up and thumbs down buttons appear after every response. Your feedback is analyzed periodically to discover patterns (e.g., if you consistently downvote long responses, Caddie learns to be more concise).
3. Conversation learning: As you use Caddie over time, it extracts context about your role, company, and preferences from your conversations and saves it to your profile.

skills.md is your personal configuration file that defines how Caddie works for you. It includes:

• Role & Context — Your role, company, industry, and ICP
• Communication Style — Preferred tone, formality, and format
• Custom Rules — Specific instructions you've given (highest priority)
• Installed Skills — The workflows you've added
• Learned Preferences — Patterns discovered from your feedback

This file is injected into every interaction, so Caddie always has your full context. It's stored securely and is private to you.

Yes. Just tell Caddie what you want it to remember. Custom rules are the highest-priority instructions in your profile. Examples:

• "Always sign off emails with 'Best, [Name]'"
• "Never mention competitor X by name in posts"
• "When drafting LinkedIn posts, keep them under 150 words"
• "My calendar link is calendly.com/myname — use it when scheduling"

The App Home is Caddie's dashboard inside Slack. Click on Caddie in your Apps sidebar, then click the Home tab (not Messages). From here you can:

• See all your connected tools and connect/disconnect them
• View installed skills and install/remove skills
• See active scheduled workflows and pause/resume them
• Access quick links to the Skills Library and Integrations

Some skills run on a schedule instead of on-demand. For example:

• Morning Roundup — Runs every weekday morning and posts a prioritized briefing to your Slack DM
• EOD Recap — Runs every weekday evening with a summary of what happened and what's left
• Meeting Prep — Runs 30 minutes before each meeting with context on attendees and talking points
• Signal Detection — Runs every 2 hours during business hours to catch buying signals
• Weekly Pipeline Report — Runs every Friday afternoon

Install the skill (see above) and the schedule activates automatically. Caddie will post results to your Slack DM at the scheduled time. You can pause or resume scheduled skills from the App Home tab.

Yes. Tell Caddie something like "Every morning, check my email and summarize anything urgent" and it will offer to save it as a scheduled workflow. You can set daily, weekly, or business-hours schedules.

Tool authorizations can expire if the provider revokes access (e.g., you changed your Google password). Try disconnecting and reconnecting the tool:

1. Go to App Home and click Disconnect on the tool
2. Click Connect again and re-authorize

If the issue persists, contact support@caddieagent.ai.

Check the following:

• Make sure you're messaging Caddie in a direct message, not a channel (unless you're mentioning @Caddie in a thread)
• Check that Caddie is still installed in your workspace (look under Apps in the sidebar)
• Try sending a simple message like "hello" to restart the conversation

If Caddie is still unresponsive, there may be a temporary service issue. Contact support@caddieagent.ai.

Try these steps:

• Be more specific — Instead of "draft a post," try "draft a LinkedIn post about our new feature, targeting marketing leaders, casual tone."
• Use feedback buttons — Thumbs down on outputs that miss the mark. Over time, Caddie adapts.
• Set custom rules — Tell Caddie your preferences explicitly: "Remember: always use data and metrics in my posts."
• Check tool connections — If a skill requires multiple tools, make sure all are connected and active.

Go to Slack Settings → Manage Apps → Caddie → Remove. This removes Caddie for all users in the workspace. Individual users can stop using Caddie at any time by simply not messaging it — there's nothing to uninstall on a per-user basis.

If you want your data deleted, email support@caddieagent.ai and we'll process the request promptly.

Caddie is powered by large language models (LLMs) including Claude by Anthropic. When you send a message, Caddie combines your request with context from your connected tools and your personal profile (skills.md) to generate responses and take actions.

Yes. Like all AI-powered tools, Caddie can produce responses that are inaccurate, incomplete, or out of date. Large language models can sometimes generate content that sounds plausible but is factually incorrect (commonly called "hallucination").

For this reason:

• Always review AI-generated content before sending or publishing. Caddie shows you every draft before any external action is taken.
• Do not rely on Caddie for legal, medical, financial, or compliance-critical decisions.
• Verify facts, figures, and claims in AI-generated content against original sources.
• Use the thumbs-down feedback button when Caddie produces inaccurate output — this helps improve future responses.

Caddie is a productivity tool designed to assist you, not replace your judgment. You remain responsible for any content you choose to send or publish.

Your data is stored in a secure, encrypted database (Supabase). Tool connection tokens are encrypted at rest. Your personal profile (skills.md) and conversation context are private to your account — no other user or workspace admin can access them.

For full details, see our Privacy Policy.

No. Your conversations, tool data, and personal profile are not used to train or fine-tune any AI models. They are used only to generate responses to your requests in real time.