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Suggesting relevant DMs to prospects

Suggestion based outbound

Oleg Sobolev avatar
Written by Oleg Sobolev
Updated over 2 weeks ago

Extrovert suggests DMs to prospects after they connect with you or when it's time to follow up. AI drafts messages based on their profile, recent posts, your conversation history, and your DM playbook. You review, edit if needed, and approve. Nothing sends without your approval.

Expected results

  • 2-5x reply rates compared to cold outreach

  • Touchpoints that feel timely and personal

  • 25%+ ghosted deals reactivated

  • 15-30 minutes daily instead of hours

How it works

Extrovert monitors your prospects and suggests DMs when certain conditions are met. You configure the triggers, and AI drafts messages when it's time to reach out. Nothing is sent without your approval—you always review first.

DM triggers

You can enable one or more triggers in Campaign → DMs tab:

First message after connected

Suggests a first DM to start a conversation after a prospect accepts your connection request.

  • Timing slider: 1 day to 2 months after connection

  • Best for: Conversation starters for new connections

☝️ Note: If you're already connected when adding a prospect, the DM will be suggested right away. As always, nothing is sent without your approval.

Follow up if prospect posts something relevant

Suggests a follow-up DM when the prospect shares something you can reference in your message.

  • Timing slider: Minimum interval since last DM (1 day to 2 months)

  • Best for: Relevant, timely follow-ups that reference their recent activity

What counts as relevant: Posts containing facts about the prospect—attended an event, shared a personal update, posted about a challenge they're facing. General thought leadership posts don't qualify because there's nothing specific to reference.

Follow up regardless after X days

Suggests a follow-up DM after a set number of days even if no relevant post was found.

  • Timing slider: 1 day to 2 months since last message

  • Best for: Ensuring you never lose touch with prospects

  • How it works: AI uses your DM playbook to find new angles and won't repeat previous conversation topics

Loops, not sequences

Traditional sequences run for 2-4 weeks and then stop. Extrovert creates an ongoing loop—it keeps suggesting DMs based on what's happening in your prospects' world. Your messages are always timely and adapted to their signals. The loop continues until they buy or you remove them from the campaign.

Learn more about the complete warm outreach workflow.

Setting up DMs

For new campaigns

When creating a new campaign with the "Reach out to prospects and nurture pipeline" goal:

  1. Click Create campaign

  2. Select Reach out to prospects and nurture pipeline

  3. Choose a preset:

    • Warm outreach - DM after connection and follow up

    • Nurture pipeline - Send monthly nurturing DMs

  4. Adjust the DM settings if needed

For existing campaigns

  1. Go to your campaign

  2. Click DMs tab

  3. Toggle on Suggest relevant DMs to prospects

  4. Configure your triggers

  5. Set your daily limit at the bottom of the page

  6. Click Save

The DM suggestions page

Find DM suggestions in the left sidebar under DM suggestions.

Filtering suggestions

Use filter dropdowns to focus on specific segments:

  • User - Filter by campaign owner (for teams with multiple users)

  • Campaign - Filter by campaign

  • Prospect list - Filter by list

Suggestion tabs

  • Need approval - DMs waiting for your review

  • Pending - DMs approved and queued to send

  • Error - DMs that failed to send

  • Sent - Successfully sent DMs

What each suggestion shows

  • Prospect name, title, campaign/list tags

  • Last messages history (expandable with "Show more")

  • Time since last message

  • Reason for suggestion - Why the DM was triggered (e.g., "shared relevant post 4 days ago" or "35 days since last message")

  • The drafted DM text

Actions you can take

  • Approve - Send the DM as drafted

  • Skip/Snooze - Postpone this suggestion (see below)

  • Customize DM - Edit the draft before sending

  • Regenerate - Get a new AI-drafted version

Skip vs Snooze

The action you see depends on why the DM was suggested:

Skip (for event-triggered DMs)

Appears when the DM was triggered because the prospect posted something relevant.

  • What it means: "I don't want to respond to this specific post/event"

  • What happens: You'll still get a suggestion when the time-based trigger fires later or when another relevant event happens

  • No date selection needed

Snooze (for time-triggered DMs)

Appears when the DM was triggered because of the "follow up regardless" time trigger.

  • What it means: "Not now, remind me later"

  • Options: 1 day, 3 days, 7 days, 14 days, 30 days, Custom

  • Smart reappearance: DM suggestion will reappear on your chosen date OR if the prospect posts something relevant before that date

DM quality

DMs are drafted using multiple data sources to make them relevant and personal:

  • Conversation history - AI sees previous DM exchanges to avoid repeating itself

  • Prospect's profile - Job title, company, background

  • Recent posts - What they've been sharing on LinkedIn

  • Your DM style - How you want to sound

  • Your DM playbook - Templates, talking points, product info

Setting up your DM style

Go to Settings → Style Library → [Style Name] → DM style instructions.

This is separate from comment style because you DM differently than you comment. Include:

  • How direct or indirect you want to be

  • How salesy or non-salesy

  • Formal vs informal language

  • Use of emojis, lowercase, sentence fragments

  • Length preferences

Learn more about improving draft quality.

Setting up your DM playbook

Go to Settings → Context Library → [Campaign] → DM playbook.

This is separate from Comment Insights Library because you want to mention different things in DMs vs comments. Include:

  • Templates for conversation starters

  • Product descriptions

  • Booking links / calendar links

  • Links to resources

  • Objection handling scripts

  • Value propositions

  • Company news and updates

  • Pricing information

Plan limitations

DM suggestions are available on Business and Pro plans:

  • Light plan: DM suggestions not available

  • Business plan: 10 DMs per day per seat

  • Pro plan: Unlimited DM suggestions

Daily limits

You can set daily limits for DM suggestions in Settings → Daily limits or at the bottom of the campaign DM settings page.

If you approve more DMs than your daily limit, Extrovert postpones them to the next day. Learn more about limits and working hours.

Common questions

Do I need to be connected to send DMs?

Yes. DMs can only be sent to prospects you're connected with on LinkedIn. Enable automatic connection requests to connect with prospects after warming them up with comments.

What if the prospect replies?

Extrovert doesn't pause DM suggestions—all triggers keep applying as long as the prospect is in the campaign. You chat with them in LinkedIn as usual. Extrovert helps you stay consistent with follow-ups so no one falls through the cracks.

I don't want to send DMs to a specific person

Move them out of the campaign. If you want to keep commenting on their posts without DMs, create a separate campaign with only commenting enabled and move them there.

Can I see the conversation history?

Yes. Each DM suggestion shows previous messages. Click "Show more" to see the full history.

How is this different from AI SDRs?

AI SDRs send messages autonomously without your input. Extrovert keeps you in control—every suggestion needs your approval. Your prospects get DMs that actually sound like you.

What if I already use a sequencer?

You can use Extrovert just for warming up and connection requests, then push connected prospects to your sequencer via webhooks. Or switch to Extrovert DMs for ongoing engagement that doesn't stop after 2-4 weeks.

Best practices

  • Set up your DM playbook first: Better context = better drafts

  • Review and edit: AI gets you 80% there, your touch makes it perfect

  • Keep commenting: DMs work best combined with ongoing engagement

  • Don't rush first DMs: Wait at least a few days after connection for better results

  • Use relevant post triggers: DMs that reference their recent activity get higher replies

  • Snooze strategically: If timing feels off, snooze rather than skip

For nurturing existing relationships, see pipeline + customer nurturing.

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