Skool DM Automation That Actually Converts

Welcome new members, convert trials, and prevent churn—all on autopilot. Send personalized direct messages at scale without being online 24/7.

92%
DM open rate (vs 20% for email)
67%
Members reply to automated DMs
3x
Higher trial conversion with check-ins
40%
Churn reduction with timely outreach

Three Workflows That Change Everything

These aren't just automated messages. They're retention machines that work while you sleep.

ONBOARDING

Welcome Sequences

New members join at all hours. You can't be online 24/7. But your welcome message can be.

  • Send welcome DM within minutes of joining
  • Day 3 check-in: "How's it going so far?"
  • Day 7 resource share: "Here's what you might have missed"
  • First post boost: Auto-like and welcome comment
  • Personalize with member name, join date, level
CONVERSION

Trial Conversion

Trials expire quietly. By the time you notice, they're gone. Automate check-ins at critical moments.

  • Day 2: "What brought you here?"
  • Mid-trial: "Have you explored X feature yet?"
  • 3 days before expiry: "Trial ending soon"
  • Custom timing based on trial length
  • Track responses, sync to CRM
RETENTION

Churn Prevention

The moment someone clicks cancel, you have one shot. Don't miss it. Automated outreach at the most critical time.

  • Instant DM when cancellation detected
  • "What's not working for you?"
  • Last-chance message before access ends
  • Win-back campaign for churned members
  • Cooldown periods to avoid spam

What the DMs Actually Look Like

These aren't robotic. They feel personal because they are personal—dynamically personalized with member data.

Welcome Sequence (sent 4 hours after joining)
Welcome to Startup Founders Club, Marcus! 🎉

I'm so glad you're here. Here are a few things to get you started:

1. Introduce yourself in the community—we'd love to get to know you!
2. Check out our getting started guide
3. Don't hesitate to ask questions—that's what we're here for

What brought you to join us?
Trial Check-In (Day 2 of trial)
Hey Sarah! 👋

How are you finding Startup Founders Club so far?

I wanted to check in and see if you have any questions. Your trial is a great time to explore everything we offer.

What's been the most valuable part for you so far?
Churn Prevention (triggered on cancellation)
Hi James,

I noticed you're thinking about leaving Startup Founders Club. I'd love to understand what's not working for you.

Is there anything I can help with? Sometimes a quick chat can make all the difference.

How DM Automation Actually Works

1

Choose Your Trigger

Member joined, trial started, cancellation detected, 3 days before trial ends, or any custom event. Runs on schedule or real-time.

2

Write Your Message

Use variables like , , . Messages feel personal because they are personal.

3

Set Smart Limits

Daily caps (50 DMs/day max), cooldown periods (don't re-contact within X days), and opt-out respect. Never spam. Always respectful.

4

It Runs on Autopilot

Messages send automatically. Track every sent DM, skip reason, and member response. Full audit trail.

Powerful Event Triggers

Go beyond scheduled DMs. Trigger messages based on what members actually do.

👋

Member Joined

Welcome new members instantly

⚠️

Cancellation Started

Reach out before they leave

💔

Member Churned

Win-back campaigns

🏷️

Member Tagged

Trigger on specific tags (VIP, at-risk)

📝

Note Added

Follow up when you add internal notes

🎓

Course Completed

Celebrate achievements

Built-In Safeguards (So You Never Spam)

Feature How It Protects Members
Global Daily Cap Max 2 DMs per member per day across ALL workflows. Higher priority workflows win.
Workflow Daily Limits Each workflow has its own daily limit (e.g., max 50 welcome DMs/day). Prevents floods.
Cooldown Periods Don't re-contact same member within X days (configurable per workflow). Once welcomed, always welcomed.
Opt-Out Respect Members can opt out of all DMs, or granular (opt out of promotional, keep important).
Priority System Critical DMs (welcome, churn) always send. Low-priority (upsells) wait their turn.
Full Audit Trail See every DM sent, who received it, when, and why. Track skips and failures.

Connect Your Entire Stack

DMs are just the start. Sync to your CRM, notify your team, log to spreadsheets. Complete visibility.

CRM Sync

  • HubSpot contact creation
  • GoHighLevel pipelines
  • ActiveCampaign tags
  • Ontraport sequences

Team Notifications

  • Slack alerts (new member, cancellation)
  • Discord notifications
  • Telegram messages
  • Email digests

Data & Tracking

  • Google Sheets logging
  • Airtable records
  • Webhook callbacks
  • API access

Email Marketing

  • SendGrid campaigns
  • Mailchimp lists
  • ConvertKit sequences
  • Custom SMTP

Multi-Channel by Design

Send DMs inside Skool AND email to their inbox. Notify your team on Slack when critical events happen. Log everything to Google Sheets for reporting. All from one workflow.

Manual DMs vs Automated (The Real Difference)

Scenario Manual Approach Automated with StickyHive
New member joins at 2am They wait 8 hours for your welcome message. First impression: delayed. Welcome DM sent within 5 minutes. First impression: you care.
10 members cancel in one day You notice 3 of them. The other 7 churn silently. All 10 get personalized outreach instantly. Save 3-4 of them.
50 trials ending this week You manually message 12. The rest expire without contact. All 50 get check-in DMs 3 days before expiry. 3x higher conversion.
Member inactive for 2 weeks You don't notice until they cancel. Auto-DM on day 14: "We miss you! Need help with anything?"
Scaling to 500+ members Impossible. You can't DM everyone. Relationships break down. Every member gets personalized attention. Scales infinitely.

Start Automating DMs Free for 14 Days

No credit card required. Set up your first welcome sequence in under 5 minutes. See why 1,200+ community managers trust StickyHive for retention.

✓ Welcome sequences that convert
✓ Trial check-ins that feel personal
✓ Churn prevention that saves members
✓ Full audit trail and CRM sync

Start Free 14-Day Trial

Takes 5 minutes to set up • Cancel anytime • No credit card required

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