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How we automated our own follow-up sequence
Follow-up is where most outreach dies. Here is how we designed the remembering and the drafting for our own outreach, while keeping a person on every send.
The problem we wanted to solve
Follow-up is where most outreach dies, and it dies for dull reasons: nobody remembers, the notes are in different places, and the second message never gets written. We wanted a system that handles the remembering and the drafting, and leaves the sending and the judgement to a person. We built it for our own outreach to local businesses, and it is also the sequence logic behind the reactivation design in how we design a lead reactivation sequence.
Three workflows
- Draft. Each day it picks about ten prospects, skips ones already contacted, researches something real to personalise on, and has the AI write a first message. It saves it as a draft in the mailbox. It never sends it.
- Detect sent. Every few hours it looks for drafts we have actually sent, and when it finds one it starts that prospect's sequence in a list in our CRM, so nobody has to log it by hand.
- Advance. Once a day it checks each prospect. If there has been a reply, the sequence stops. If not, it moves to the next step every three days: a further email or a WhatsApp task (always sent by hand), then a call task for a person, then the sequence completes.
We built and tested all three in August 2026. We are not publishing a reply rate because we do not yet have enough sends to say anything honest.
The decisions that matter
- Drafts, not sends. The AI writes the email; a person reads and sends it. WhatsApp and calls are always manual. Every message that leaves the business has been looked at. It slows us down slightly and removes the failure that matters most, a bad message sent to someone we wanted to impress. We take this stance for the reasons in what AI cannot do yet.
- A reply stops everything. The moment someone writes back, automation steps aside.
- Everything is written to the CRM, so the state of every prospect is in one place, as in our intake design.
What we would warn you about
The hardest part was not the automation but the message. A system that drafts quickly drafts a lot of mediocre messages quickly. The quality comes from what the AI is given to read about each prospect and from the rules for what it may say. We keep both short and review the drafts for the first weeks of any new list.
The same pattern, drafted by the system and sent by a person, is what sits behind our follow-up automation for Mallorca businesses.