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Review first.How a Wingman goes live.

Every Wingman starts by asking permission. Here’s how the first weeks go, and when to let it fly.

The Wingman team · · 3 min read

You wouldn’t hand your customers to a new hire on day one, however good the interview went. A Wingman is no different. Every Wingman starts in review mode: drafts wait for a person. It writes every reply and every follow-up, and nothing reaches a customer until someone on your team approves it.

Here’s how the first weeks usually go, from the setup call to the day you switch autopilot on. The examples come from Ridgeline Roofing, whose Wingman is called Dawn.

The setup call

It starts with a short call about your business: what you do, where your leads come from, and how you like to sound. Then we do the setup. We connect your number, calendar and CRM, give your Wingman its name and voice, and write its Knowledge with you.

It only picks up leads that arrive after you switch it on, so your old contacts won’t get a surprise text.

Writing the Knowledge

The Knowledge is what your Wingman knows about your business, in plain language: your services and service area, how a job happens from the first call to the finished work, the questions people ask, how you sound, and what it should never say. It also says when to hand off, like “Exact prices, insurance claims and complaints go to Tom.”

Your Wingman is told to state business facts only from the Knowledge. If yours doesn’t mention financing, it won’t offer any; it hands the question to you instead of guessing. You own the Knowledge, and you can edit it whenever something changes.

Testing replies

Before anyone is texted, you test it. In the Knowledge settings, “Test Dawn” (it carries your Wingman’s name) lets you text as a lead and see what it would send back, with the reason it chose that reply. Nothing there is sent or saved.

Try the questions your leads really ask, including the awkward ones: the price question, the complaint, the “are you a real person?”. When an answer is off, the fix is usually a sentence in the Knowledge, and you can test again straight away.

Review mode

Then your Wingman starts working. When a lead texts, it drafts the reply. In the inbox, the draft is pinned above the composer and the conversation shows “Dawn drafted”. Everything waiting also collects in Approvals, grouped by person, with the lead’s last text quoted above each draft.

Approvals is built to be cleared from the keyboard: J and K move to the next and previous draft, A approves, D discards and E edits. An approved reply sends when you approve it, at any hour.

Approvals in review mode. Drafts wait, grouped by person, until someone approves, edits or discards them.

This stage is where you tune it. If you find yourself making the same edit again and again, that’s a line for the Knowledge.

What changes on autopilot

When the drafts you’re approving are the ones you’d have written yourself, switch autopilot on. Replies and follow-ups then send on their own, inside texting hours, and at most 4 automated texts per person a day.

Some drafts still wait for a person, autopilot or not:

  • Anything that mentions a price
  • A text that runs longer than a text should
  • A link to anywhere but your own website
  • A draft that claims to be a person, or names a time your calendar didn’t offer
  • Handoffs and closing lines
  • Anything it isn’t confident about

Booking has its own setting. Your Wingman can suggest a booking for you to approve or, once autopilot is on, book on its own. Either way, it offers only times that are really open on your calendar, and the confirmation goes out after the booking is on the calendar.

The per-person switch

Autopilot is one switch for your whole Wingman. There’s a second one on every conversation: the switch at the top of a thread turns your Wingman on or off for that one person, so you can take over a delicate customer without changing anything else. And if you text a lead yourself, your Wingman steps back from that conversation on its own.

You can also go back. Switching back to review stops anything already queued, and every new draft waits for you again. Review mode isn’t a phase you graduate from. It’s there whenever you want it.

The Wingman team · Sep 25, 2026

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