How I use AI to build a 9% reply cold email sequence from scratch

Most reps open ChatGPT, type "write me a cold email sequence" and wonder why it reads like everyone else's.

The problem is the inputs. Give AI nothing to work with and it writes the same generic email every other rep is sending.

This is the exact process I use to build a cold email sequence from scratch. It's how I get a 9% reply rate, and it's the same process I walk reps through on my coaching calls.

Seven steps, then where AI actually comes in. Let's get into it.

Before you touch AI, look at who actually bought.

Their title. The trigger that was there when they bought. The pain they said yes to.

Then map the pains. One persona, one pain, one cost of inaction.

"It takes a lot of time" is too vague. Who cares? Go one level deeper and ask "which means what?" until it hits a number they're measured on.

That number is the KPI you tie the pain to.

I explain it with a band-aid. If I offer you a huge band-aid for a tiny paper cut, you'll shrug. If that paper cut is over your femoral artery and you'll bleed out in three minutes, you'll take it.

The gap between where they are and where they want to be is what gets someone to respond.

And don't try to cover everyone. Five ICPs with five personas is 25 sequences, and nobody maintains that. Pick your core two and nail those first.

When you nail the pains, the messaging is easy.

A trigger is the reason you're reaching out to this person right now.

The ones I use most:

Job change: They just started a new role.

Headcount growth: The team is expanding.

Open roles: They're actively hiring.

Closed lost: They looked at you before and didn't buy.

Downloaded a resource: They raised their hand.

Here's the part most reps miss. For each new trigger, you duplicate the sequence and change the first line.

Everything else stays the same.

One sequence. One line changes.

Not every account deserves the same effort.

Three things decide where an account goes: does it fit your ICP, is there a trigger, and how big could the deal be.

Tier 1: Manual, multichannel, high context. I only go this personal when the deal could be at least double my normal deal size.

Tier 2: The sequence.

Tier 3: Waits until the signals show up.

Accounts move. A Tier 3 with a new trigger can be a Tier 1 next week.

So re-tier every week.

Your first email uses T.I.P.S.: trigger, implication, pain, social proof, solution, soft CTA.

Trigger: Why you're reaching out, right now. A new hire, a new office, a webinar they attended. Lead with it.

Implication: Plant the seed of what's probably on their mind. "Curious how you're thinking about..." Hold the pain for the next line.

Pain: The problem and its cost of inaction, tied to a KPI.

Social proof: Who you've helped and the outcome they got.

Solution: How you got them that outcome. Keep it brief, the detail is for the call.

Soft CTA: "Worth a chat?" Never ask for 15 minutes. That's too much friction for a stranger.

Here's an opening one of my reps on a North American expansion team used: "Noticed you opened three new offices last quarter. Curious how you're tracking payroll for the new hires."

Then the pain: "Companies usually run a separate payroll provider for each country, which often leads to fragmented processes and 18% higher costs." After that comes one line of proof, one line on how they help, and a soft CTA.

Keep the whole email under 125 words. Write it simply, because the lower the reading level, the more replies you get.

Then the subject line. Its only job is to get the email opened, so make it boring enough to look internal.

Whatever the pain of the email is, that's the subject line. When I sold to CFOs, mine were things like "exchange rates".

One email. One pain. One cost of inaction. One solution.

A thread is one subject line plus every reply stacked under it. A new subject line starts a new thread.

My rule is a maximum of 4 emails in one thread. Past that it feels like you're hammering them, and a long chain they've already ignored makes a reply less likely.

So after the first thread, start a new one with a different pain.

Every bump needs a new reason to reply. Never just "thoughts?"

The bumps I use:

Resource bump: Share a relevant article tied to the pain and nod back to your first email.

Thoughtful bump: Add context first, then bump.

Case study bump: A quick breakdown of how you helped someone with the same problem.

Focus bump: "Saw you've hired multiple SDRs in EMEA. Usually that means a focus on scaling outside the US. Is that the case for you?"

Referral bump: "Assuming this doesn't fall under your scope, would it make more sense to talk to someone else?"

Most reps still send "any thoughts?" as a follow-up. That's exactly why this still works.

Now put it together. Seven emails across two threads.

Thread one is pain 1:

Day 1: The T.I.P.S. email.

Day 3: Resource bump.

Day 5: Thoughtful bump.

Thread two is pain 2, with a new subject line:

Day 12: A new T.I.P.S. email on pain 2.

Day 15: A value bump on pain 2.

Day 18: Focus bump.

Day 21: Referral bump.

Your Tier 1s get calls and LinkedIn on top of this.

Then run it on at least 100 prospects before you judge it. On 50, a couple of replies either way is the difference between 5% and 10%.

Seven emails. Two pains. 21 days.

So where does AI come in? Only once you've done the first part: your closed-won, your pains, your triggers and your list.

Here's how I use it:

Treat what comes back as a base to work off.

You still need to know how to write it without AI. Otherwise you can't tell a good email from a bad one.

Without the inputs, AI just writes slop faster.

And remember, the only job of a cold email is to get a response. Even a no gives you feedback, and a lot of the time you can just pick up the phone and call them.

AI writes the email. You do the thinking.

Now this is all you need to win today.

But having the time to build this is something else.

So if you do want our support, check out Outbound OS. Book a call

Do you know the trigger and the pain behind your closed-won deals? If not, go pull them today.

Does your first email follow T.I.P.S. in under 125 words? If not, go rewrite it today.

Does every follow-up give them a new reason to reply? If not, go split your sequence into two threads today.

Do those 3 things before you open ChatGPT, and AI will finally write something worth sending. Go build it today.