What this does

This is a Claude Skill: a set of instructions you upload once, after which Claude knows how to run your competitor-signal outbound program end to end.

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Prerequisite: Connect Letterdrop to Claude (via MCP)

It works in two parts.

Part 1 — Setup (once, ~20 minutes)

Claude asks you a short questionnaire, researches your ICP and buyer personas from your website and your Letterdrop data, and drafts problem-centric email templates for each persona. You review and edit every template in chat. Nothing is saved until you approve it.

Part 2 — Daily run (~2 minutes of your attention)

Each day, Claude:

Pulls new competitor signals from Letterdrop — people at target accounts who engaged with a competitor's reps

Decides who's actually worth reaching out to (ICP fit, signal freshness, no prior outreach)

Finds each person's email via your CRM record in Letterdrop, or your connected outreach tool

Writes a personalized subject line, email, and follow-up using your approved templates

Pushes each lead into your existing sequence in Smartlead, Apollo, or HubSpot

Sends you a summary of what went out

What you need before you start

Requirement	Notes
Claude plan	Pro, Max, Team, or Enterprise
Code execution enabled	Settings → Capabilities → Code execution and file creation
Letterdrop connector	Connected in Claude, with access to your competitor monitoring workspace
An outreach tool connector	Smartlead, Apollo, HubSpot, or similar
An existing sequence	Already built and configured in that tool — the skill never creates one

Step 1 — Enable skills in Claude

Team and Enterprise plans: Your organization owner goes to Organization settings → Skills and confirms both Code execution and file creation and Skills are toggled on.

Pro and Max plans: Go to Settings → Capabilities and confirm Code execution and file creation is on.

Settings → Capabilities with "Code execution and file creation" toggled on.

Step 2 — Upload the skill

Go to Customize → Skills (claude.ai/customize/skills)

Click the "+" button, then "+ Create skill"

Select "Upload a skill"

Upload signal-based-outreach.zip

The skill appears in your list — make sure its toggle is on

The Customize → Skills page with the "+" button.

The "Upload a skill" dialog with the ZIP file.

The skill in your list, toggled on.

Team and Enterprise: An owner can upload it once under Organization settings → Skills instead, which provisions it to everyone automatically.

Step 3 — Connect your tools

In Claude, connect:

Letterdrop — for competitor signals

See: Connect Letterdrop to Claude (via MCP)

Your outreach tool — Smartlead, Apollo, etc

Connectors page showing Letterdrop and the outreach tool connected.

Step 4 — Run setup

Start a new chat and say:

Set up /signal-based outreach

Claude will ask you nine questions:

Your company — name and website

Letterdrop workspace — confirm the workspace connected

Outreach tool — which connected tool holds your sequences

Sequence — which existing sequence to push leads into

Send mode — auto (sends on your tool's schedule) or review (drafts you release manually)

Daily cap — how many leads per day (25–50 recommended)

Who to target — which Letterdrop priorities, and whether to include buying-committee decision-makers

Digest — where to send the daily summary (a Slack channel, or just in chat)

Where to store settings — a Google Drive folder, or a local path

Tip: Choose review mode for your first week. Once the output looks right, switch to auto.

Step 5 — Approve your templates

Claude researches your ICP, defines 4–6 buyer personas, and drafts for each:

A signal-triggered email — for people who personally engaged a competitor

An evergreen email — for decision-makers who didn't

A follow-up

Every email ends with one concrete offer (a 15-minute walkthrough, a teardown of their setup — something specific).

Read them, ask for changes, and approve. Claude saves the approved set and uses only those from then on.

Step 6 — Schedule the daily run

The skill doesn't schedule itself. Set up a recurring daily task in Claude that says:

Run today's signal-based outreach

Or just run it manually each morning with the same message.

What a daily run looks like

Signal-based outreach — 17 Sep

Pulled:     34 new contacts from Letterdrop
Enrolled:   22 into "Competitor Signal — CS Leaders"
            14 signal-triggered (VP Customer Success persona)
             8 evergreen (Chief Customer Officer persona)
Skipped:    12
             6 no verified email
             4 stale signal
             2 already in an active sequence
Errors:     0
Send mode:  auto

Signal-Based Outreach in Claude