Letting the AI SDR send: messages, follow-ups and replies

Step 1Switch actions on one at a time

An AI SDR drafts, sends, follows up, reads replies, books meetings and writes to the CRM. A mistake costs something different in each, so switch them on one at a time, as in support part 7. Example Software, an invented company that sells to finance teams, uses this order:

Booking is two actions. HubSpot’s prospecting agent shares a meeting link you choose, and the contact picks the time. Instantly’s reply agent, when a prospect confirms a time, “schedules the meeting directly in Calendly”. Switch the link on first.

Step 2Approve the first message, let follow-ups go

A HubSpot user asked for exactly this on HubSpot Ideas:

The agent would then send the follow-ups on schedule until the contact replies, books a meeting or reaches the send limit. A rep reading the first message checks what no follow-up can fix: the person, and the reason to write.

What to set: in HubSpot, choose “Review emails” on the prospecting agent’s Automation tab; it covers every email, follow-ups included. In Artisan, keep a campaign’s Full Autopilot switch off until its first messages need no edits; once it’s on, Ava sends without approval but leaves replies to you. In Instantly, run the AI Reply Agent in Human-In-The-Loop mode. In Reply.io, start each reply handler on Draft, then move them to Auto one by one.

Once follow-ups go alone, nobody reads them first, so each send is one action: the contact rules checked before it (part 8), a record after it (part 13), and a key, so a retry doesn’t send twice (support part 7).

Step 3Give each kind of reply its own action

Reading a reply is an action too, since the label decides what follows: in Smartlead, a category can start a subsequence, such as a “Send more info” drip for a lead marked “Requested info”. So write down what follows each kind:

An interested reply ends the sequence and goes to the contact’s owner (part 9).

“Please remove me”, in any words, is an unsubscribe: record it in the CRM, which holds who unsubscribed, so every sequence and person sees it (part 6). HubSpot’s sequences page lists the unsubscribe link and a reply among the reasons a contact leaves a sequence, and says nothing of a written request becoming an opt-out: set that up yourself, and test it (part 10).

Step 4Tell an auto-reply from a reply

An out-of-office taken for a reply can end a sequence early. HubSpot’s sequences page names one gap: “Gmail out-of-office replies sent to Outlook inboxes aren’t recognized and therefore contacts will be unenrolled from the sequence.” So read the header first:

It says SHOULD, so when the field is missing, read the words.

Hold follow-ups until the return date, and check whether your tool can read it. Reply.io’s page says its system “cannot detect the days mentioned in the email”, so it resumes everyone after the same set number of days. Outreach found in 2019 that resuming by a set rule restarted nearly 16% of sequences too early, and almost 60% after absences of over two weeks.

Then read the contact’s next message afresh. Smartlead’s page says that before a fix, once a lead was marked out of office, “any subsequent replies from that lead would still be categorized as OOO”.

When an auto-reply names a colleague, AiSDR’s page says it adds that address to your campaign and “sends a personalized message to the suggested contact”, without telling you each time. That colleague hasn’t written to you: contact rules first (part 8), and a rep approves the first message (step 2).

Next in this series

Part 8: contact rules: unsubscribes, frequency caps and who never to contact. See all 13 parts.

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