Insaight — Draft Cold Outreach

Craft personalized cold messages from three inputs:

1. The intelligence brief from a prior research skill (conversation context).
2. The learned memory — insaight:get_memory() returns the distilled style guide (the user's voice) and playbook (strategies with reply-rate evidence).
3. The outreach ledger — prior-contact check via insaight:list_outreach().

All tools must be loaded first via tool_search(query="insaight").

Step 1 — Verify research exists

Look in the conversation for:

• 👤 Role & Context + 🪝 Outreach Hooks (person research), OR
• 🏢 Company Snapshot + 🎯 Prospect Evaluation (company research).

Without a brief there is nothing to personalize with, and a generic message sent under the user's name costs them more than sending nothing. Stop and offer the research instead:

"I don't have research on this person/company yet. Want me to run insaight-research-person or insaight-research-company first?"

Step 2 — Load the memory (STYLE + PLAYBOOK)

insaight:get_memory()

Read the memory rather than trawling raw sent history. The memory is what earlier reflection runs distilled from messages the user approved and from outcomes that actually landed; raw history is unfiltered and pulls a draft toward whatever the most recent message happened to sound like.

• If style_learned is true: treat the style file as the voice source of truth and follow it closely — it was distilled from real approved sends.
• If playbook_learned is true: prefer hooks and variants the playbook marks as working, treat its "hypotheses" as worth testing, and leave anything in its "Retired" section alone — it was retired because it stopped working.
• If neither is learned yet (fresh install): fall back in this order — (a) insaight:list_outreach(limit=10, full=true) to read recent real sends, (b) the user's Notion outreach log if one is configured (get_config() → NOTION_OUTREACH_LOG), (c) the fallback principles in Step 4. Mention once: "No learned style memory yet — after a few logged sends and outcomes, run insaight-reflect and drafts will match your voice."

Cache the memory for the whole conversation. Re-fetching between iterations adds nothing (it only changes on a reflection run) and slows the loop down.

Step 3 — Check for prior contact

insaight:list_outreach(target="name or profile URL or company")

Do this before drafting, not after. A second cold opener to someone already contacted reads as spam and quietly costs the user the relationship — and the ledger is the only place that remembers.

If records come back:

"⚠️ The ledger shows you messaged [Name] on [date] (outcome: [outcome]). Is this a follow-up? If yes, I'll draft a follow-up; if this is a mistake, tell me who you actually want to reach."

A follow-up is a different message from a first touch: acknowledge the earlier contact, point at what specifically changed since (new post, new funding, new role), and keep the ask smaller than last time.

Step 4 — Draft (matching the learned style)

Produce two variants, each in both formats:

Variant A — Warm / Story-led

Open with a specific observation or shared detail. Build before the pitch.

Variant B — Direct / ROI-led

Open with the pain or opportunity. Get to the point faster.

Two angles let the user pick by feel for the recipient, which they can judge better than you can. If the playbook shows one variant or hook type clearly outperforming on real numbers, say so and lead with it — but still offer both unless the user asked for one.

Formats per variant:

• LinkedIn DM — matching the typical DM length from the style memory.
• Email — matching the typical email length and subject-line style from the style memory.

Fallback principles (only when no memory and no history exists)

• Lead with a specific observation from their posts — not generic flattery.
• Name the pain at their scale, specifically enough that they think "this person gets my situation."
• One-sentence value prop tied to that pain.
• Social proof only when it's genuinely comparable.
• Soft CTA — a question, or fifteen minutes. Never a demo push.
• Peer-to-peer and confident: no apologizing for the message, no exclamation marks. Cold outreach is judged on whether the sender sounds like an equal.
• Match the language the person posts in.

Step 5 — Show your work

When presenting the drafts, note briefly:

• Which style signals you followed from the memory (1–2 lines).
• Which playbook evidence drove the hook or variant choice, if any.
• Which commonality or hook from the research you're leading with.

The user is about to send this under their own name, so make the reasoning checkable before they copy anything.

After drafting

• Offer to iterate: "Want me to adjust the angle, tone, or CTA?"
• When the user says they sent a message, log it immediately via the insaight-track-outreach skill (log_outreach with the exact sent text, variant, and hook_type). Unlogged sends are invisible to the prior-contact check and never teach the memory anything.
• Do not write to Notion.