SimonTheSalesBooster Skill: Cold Email Sequence Builder
What This Skill Does
Builds a complete, ready-to-send cold email sequence for a specific ICP and use case — including subject lines with A/B variants, a multi-touch cadence (first touch through breakup), and personalization tokens for each message. Outputs copy that is short, specific, and designed to get replies, not opens.
When to Use
- You need to launch a new outbound sequence for a specific segment or persona
- Your current cold email reply rate is below 3% and you need a rebuild
- You're targeting a new vertical and need email copy from scratch
- You have an Apollo, Instantly, Lemlist, or Outreach sequence to fill
- You want to test a new value proposition or pain angle via email
Inputs Required
Before running this skill, ask the user for:
- ICP — exact title, industry, and company size of the person receiving the emails
- Core pain point — the single biggest problem you solve for this persona (one sentence)
- Your solution — what you do, in plain language, no jargon
- Proof point — one specific result you've delivered for a similar customer (e.g., "helped X company go from 20 to 60 demos/month in 90 days")
- Desired CTA — what action do you want from the reply? (book a call, reply with interest, intro to the right person, etc.)
- Sequence length — how many touches? (default: 5 over 14 days)
- Tone — direct/founder, warm/consultative, or challenger/provocative?
Step-by-Step Instructions
Step 1 — Define the Core Message Architecture
Before writing a single email, establish:
The Pain Angle: The specific, costly problem this persona loses sleep over. Not a generic industry trend — a concrete, felt frustration. Write it as they would say it internally, not as a vendor would describe it.
The Contrast: What does life look like before vs. after your solution? One clear before/after statement.
The Proof Anchor: The single most credible data point or customer story you have. This will rotate across the sequence.
The Objection to Pre-empt: What's the most common reason this persona doesn't reply? (Too busy, not the decision-maker, already have a solution, skeptical of vendors.) Build the sequence to address this silently.
Step 2 — Build the 5-Touch Cadence
Write each email separately. Every email must:
- Be under 100 words (75 is better)
- Have one clear CTA — never two
- Avoid attachments, case study links, or calendly links in touches 1–2
- Sound like it was written by a human, not generated by a template
Email 1 — Day 1: The Specific Hook Open with one hyper-relevant observation about their world (not a compliment). State the pain. Bridge to your solution in one sentence. Ask for a reaction, not a meeting.
Subject line: Write 3 variants — one curiosity, one direct, one pattern-interrupt.
Email 2 — Day 3: The Different Angle Do not repeat email 1. Come at the pain from a different direction — the cost of inaction, a trend their peers are responding to, or a question that makes them think. End with the same low-friction CTA.
Subject line: Reply thread (Re: [original subject]) OR a fresh subject. Write both options.
Email 3 — Day 7: The Proof Drop Lead with the customer result. Make it specific: numbers, timeframe, company type. One sentence. Then connect it to their situation. Offer the next step as "worth a 15-minute conversation to see if you'd get similar results."
Subject line: Write 2 variants — one that references the result, one that references the persona's goal.
Email 4 — Day 10: The Soft Challenger Ask a question that surfaces the cost of their current approach. Not confrontational — genuinely curious. Something that makes them think "actually, how ARE we handling this?" End with: "Happy to share how others in your position are solving this."
Subject line: Question-based. One variant only.
Email 5 — Day 14: The Breakup Short, honest, no-pressure. Tell them you won't follow up after this. Give them one last easy out (forward to the right person, reply "not now" and you'll check back in 6 months). Leave the door open permanently.
Subject line: "Closing the loop" or similar. One variant.
Step 3 — Build the Personalization Token Map
For each email, define the personalization tokens that make it feel 1:1:
| Token | Where to Find It | Which Emails |
|---|---|---|
| {{first_name}} | Contact data | All |
| {{company}} | Contact data | 1, 2 |
| {{trigger_event}} | LinkedIn / Crunchbase | 1 |
| {{their_industry_pain}} | Research or ICP assumption | 2 |
| {{competitor_or_current_tool}} | Apollo / ZoomInfo technographic | 3 |
| {{mutual_connection}} | Optional, Email 1 | |
| {{their_recent_post_or_news}} | Google / LinkedIn | Optional, Email 1 |
Flag which tokens are required vs. optional for each email. Sequences should send even if optional tokens are blank.
Step 4 — Write the Full Deliverable
Produce all 5 emails in send-ready format:
EMAIL 1 — Day 1
Subject A: [option 1]
Subject B: [option 2]
Subject C: [option 3]
Body:
[full email copy with tokens in brackets]
CTA: [exact ask]
---
Repeat for emails 2–5.
Step 5 — A/B Test Recommendations
Recommend 2 A/B tests to run on this sequence:
- Subject line test — which variant of Email 1's subject to split test first, and what metric to watch (open rate, not reply rate)
- CTA test — compare the current CTA against a softer or harder alternative, and which email to run it on
Output Format
Deliver:
- Message Architecture — pain angle, contrast, proof anchor, objection to pre-empt (one paragraph each)
- Full 5-email sequence — send-ready, with subject line variants
- Personalization Token Map — table showing required vs. optional tokens per email
- A/B Test Recommendations — 2 specific tests with instructions
- Sequence Setup Notes — recommended sending tool settings (send window, daily cap, reply detection, auto-pause on out-of-office)
Pro Tips
- The #1 reason cold emails fail is length, not copy. Cut every email by 30% after writing it. If it can be said in 60 words, don't use 90.
- Never put a Calendly link in Email 1. It signals "I send this to everyone." Ask for a reply first. Send the link only when they've expressed interest.
- The breakup email (Email 5) often gets the highest reply rate in the whole sequence. Write it like you mean it — not as a manipulation tactic. Real brevity and honesty lands.
- Rotate the pain angle between emails. If Email 1 focuses on lost revenue, Email 2 should focus on wasted time or team friction. Different angles hit different people.
- Subject lines under 5 words outperform longer ones in cold outreach consistently. Test: "Quick question, {{first_name}}" vs. "How [Company] handles [pain]" vs. "[Mutual connection] suggested I reach out."
- Pause the sequence automatically on out-of-office replies. Sending Email 3 to someone on vacation and Email 4 when they return creates negative first impressions.
Example Output Snippet
ICP: VP of Sales at B2B SaaS companies, 50–500 employees, Series A–C
Pain Angle: Reps are busy but the pipeline is thin. They're logging activity in the CRM but deals aren't moving. The VP can't tell if it's a hiring problem, a coaching problem, or a messaging problem — and they don't have time to figure it out.
EMAIL 1 — Day 1
Subject A: pipeline vs. activity Subject B: {{first_name}} — quick question about your team's pipeline Subject C: the gap between CRM activity and closed revenue
Body: "{{first_name}} — most VP Sales I talk to have the same problem: reps are busy, the CRM looks healthy, but the pipeline coverage isn't there.
We help B2B SaaS sales teams close that gap without adding headcount. Did it for [Customer] — took them from 1.8x to 3.4x coverage in one quarter.
Worth a 10-minute call to see if you'd see similar numbers?"
CTA: Reply with a yes or a time that works.