Cold Outreach Sequence Here's what I've learned about cold outreach: the word "cold" is the problem. Spray-and-pray templates don't work. 10 minutes of research + a specific reference = not cold anymore. This skill builds the second kind. Mode Detect from context or ask: "One message, full sequence, or full outreach system?" Mode What you get Best for quick 1 connection request + 1 follow-up for a single prospect Testing an angle, one-off outreach standard Full 4-touch sequence for a single prospect Active pipeline, individual targets deep Multi-prospect sequence system + A/B variants + tracking framework Launching an outreach campaign Default: standard — use quick if they give you one name and say "draft something." Use deep if they're building a repeatable outreach engine. Context Loading Gates Before writing any message, collect: Prospect name and company — full name, company, role/title Research signals — run tool calls first (see below); do not write without them Sender positioning — what does the sender do, for whom, with what result? (Use positioning-basics output if available) Platform — LinkedIn DM, email, or both? Batch size — how many prospects? (determines tier assignment) Research tool calls — run before writing: web_search('[Company] [Founder/Name] news 2026') web_search('[Company] funding recent') web_search('[Person name] [Company] LinkedIn') Personalization constraint: Do not write a Tier 1 message without a named specific signal from research. If search yields 0 signals, default to Tier 3 and say so explicitly. Phase 1: Research & Signal Assessment For each prospect, document findings before drafting: Signal types (ranked by message strength): Recent news event (funding, launch, hire, press) → strongest signal Recent LinkedIn post activity → strong signal Company stage/growth data → medium signal Role + industry awareness only → weak signal (Tier 3) Personalization tier assignment: Research Result Tier Approach Named signal (news + post + context) Tier 1 Fully custom, reference signal in every message Company info + role context Tier 2 Template + personalized opener No signals found Tier 3 Volume template, minimal customization Phase 2: Sequence Generation Connection Request (LinkedIn) — 300 chars max Formula: [Specific observation from research] + [Simple reason to connect] Rules: No pitching Prove you did research (name the signal) One sentence, conversational Never "I'd love to pick your brain" By signal type: Recent funding: "Congrats on the Series A — the [investor] backing is a smart signal. Would love to connect." Recent post: "Your post on [specific topic] resonated — been thinking the same thing. Happy to connect." News/launch: "Saw the [product] launch — [specific detail] is smart positioning. Would love to connect." First Message (After Accept — Wait 24-48 Hours) Formula: [Thanks] + [Bridge to relevance] + [Light value] + [Soft question] Template: Thanks for connecting. I work with [ICP description] on [specific outcome]. Curious — is [relevant function] something you own directly at [Company], or is that still founder-led? Happy to share what I'm seeing work at similar-stage companies either way. Follow-Up #1 (Day 7) Formula: [Light nudge] + [New signal or angle] + [Easy out] Constraint: Do NOT write "following up" with nothing new. Add one new piece: A relevant article or trend A related insight you recently had A connection to something they posted Template: Bumping this up — came across [specific article/trend/insight] and thought of your situation at [Company]. [One sentence on why it's relevant to them.] Happy to share more if useful. If not, no worries. Follow-Up #2 (Day 14) Shift to email if LinkedIn hasn't converted, or try a different angle. Subject line options: "[Company]'s [function] as you scale" "Saw your [post/news] — quick thought" "Question about [specific thing they're doing]" Email structure: [1-line hook tied to their specific situation] [2-3 sentences: why you're reaching out + one proof point] [Soft CTA — 1 sentence] Break-Up Message (Day 21) I'll assume timing isn't right — totally get it. If [relevant pain point] becomes a priority down the road, happy to reconnect. Best of luck with [specific thing they're working on based on research]. Post-break-up action: Add to 6-month re-engagement list with a resurface date. Phase 3: Self-Critique Pass (REQUIRED) After generating the full sequence, evaluate: Does every message reference the specific signal from research, or are they generic? Is the connection request under 300 characters? Does the first message ask a question (invite dialogue) rather than pitch? Does follow-up #1 add something genuinely new, or is it just "following up"? Does the break-up message reference something specific about their situation? Did I correctly assign the personalization tier, or am I over-personalizing a Tier 3 prospect? Flag any issue: "The first message doesn't include a soft question — it reads as a pitch. Revised to invite dialogue." Pipeline Tracking Table Always output a tracking table for the batch: | Prospect | Company | Platform | Tier | Sent Date | Response | Stage | Next Action | Resurface Date | |
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| | [Name] | [Co] | LinkedIn | 1 | [date] | — | Connection sent | Wait 24-48h | — | | [Name] | [Co] | Email | 2 | [date] | — | First email sent | Follow-up Day 7 | — | Iteration Protocol After each response (or non-response), ask: Did the connection request get accepted? If low acceptance rate → revise the observation line Did the first message get a reply? If no → was the question soft enough, or did it feel like a pitch? Did follow-ups get ignored? If yes → try a different angle or acknowledge the silence directly Output Structure
Outreach Sequence: [Prospect Name] — [Date]
Research Summary
Signal type: [news / post / company info / none]
Signal found: "[Specific detail]"
Personalization tier: [1/2/3]
Source: [URL or platform]
Sequence ** Connection Request (LinkedIn): ** [Text — max 300 chars] ** First Message (Day 1-2 after accept): ** [Text] ** Follow-Up #1 (Day 7): ** [Text] ** Follow-Up #2 (Day 14): ** Platform: [LinkedIn / Email] Subject: [if email] [Text] ** Break-Up (Day 21): ** [Text]
Pipeline Entry | Prospect | Company | Platform | Tier | Stage | Next Action | Resurface Date | |
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| | [Name] | [Co] | [Platform] | [Tier] | Connection sent | Wait 24-48h | — |
Self-Critique Notes [Any issues flagged + revisions made] Skill by Brian Wagner | AI Marketing Architect | brianrwagner.com