Two Ways to Automate Skool DMs
Pick your approach: activate a pre-built template in 2 minutes, or build custom DM workflows from scratch with our visual builder.
Pre-Built Templates
11+ ready-made DM workflow templates. Pick one, customize the message, activate. Done in under 5 minutes.
- Welcome sequences
- Trial conversion series
- Churn prevention
- Course nudges & celebrations
- Win-back campaigns
Best for: Getting started fast
Custom Workflow Builder
Build unlimited DM workflows from scratch. Pick triggers, add conditions, chain actions with delays. No code required.
- Any trigger + any action
- Conditional logic (AND/OR)
- Multi-step sequences with delays
- DM + email + CRM combos
- Unlimited workflows
Best for: Complex member journeys
11+ Pre-Built DM Workflow Templates
Every template is designed for a specific Skool use case. Just customize the message and activate—no technical setup required.
Onboarding Templates
New Member Welcome
Auto-DM within minutes of joining. Introduce them to the community, share getting-started resources, and ask what brought them here.
- Triggered instantly when someone joins
- Personalized with their first name, community name, and more
- Optional: also send welcome email (DM + email combo)
- Optional: notify your team on Slack
- Optional: add to CRM automatically
Day 3 Check-In
Follow up 3 days after joining to see how they're settling in. Catch confusion early before disengagement sets in.
- Auto-triggers X days after joining (configurable)
- "How's it going so far? Need help with anything?"
- Share resources they may have missed
- Cooldown prevents duplicate messages
New Member Post Boost
When a new member makes their first post, automatically boost it with a like and welcome comment. Makes them feel seen.
- Triggered when a new member makes their first post
- Auto-like their first post
- Send encouraging DM or comment
- Dramatically increases Day 7 retention
Conversion Templates
Trial Conversion Check-In
Check in with trial members at strategic moments. Ask what brought them here, highlight key features, build the relationship.
- Triggered when a member starts their trial
- Day 2: "What brought you here?"
- Mid-trial: "Have you explored X yet?"
- Custom timing based on your trial length
- Sync responses to CRM
Trial Ending Soon
Automated reminder when trial is about to expire. Configurable: 3 days before, 48 hours, or last day.
- Triggered automatically before trial expires
- You choose how many days before expiry to trigger
- "Your trial ends in X days—here's what you'll lose"
- Can send DM, email, or both simultaneously
- Priority 1: always sends, never deprioritized
Retention Templates
Churn Prevention
Instant DM when cancellation is detected. Your one shot to save a member who's about to leave.
- Triggered the moment a cancellation is detected
- "What's not working for you?"
- Priority 1: bypasses daily caps—critical messages always send
- Cooldown prevents harassment
- Optional: alert team on Slack/Discord
Access Ending Soon
Last-chance message before a member's access expires. Final opportunity to save them.
- Timed trigger before access expiration
- "Your access ends soon—we'd hate to see you go"
- Highlight what they'll miss
- Can include special retention offers
Win-Back Campaign
Re-engage churned members. Reach out after they've left with a compelling reason to return.
- Triggered after a member's access ends
- Configurable delay after churn (7 days, 14 days, 30 days)
- "Here's what you've been missing..."
- Lower priority: respects member space
- Cooldown: won't re-contact for X days
Engagement & Course Templates
Level-Up Celebration
When a member levels up in Skool, automatically congratulate them. Recognition drives continued engagement.
- Triggered on level change detection
- "Congrats on reaching Level 3!" (auto-fills their level)
- Personalized with their achievement
- Optional: tag as "engaged" in CRM
Course Completion Celebration
When a member finishes a course, celebrate and guide them to the next step.
- Triggered when a member finishes a course
- Personalized with the course name
- "Huge congrats on finishing [Course Name]!"
- Suggest next course or community action
Course Nudge
Members who started a course but haven't progressed get a gentle nudge to continue.
- Triggered when course progress stalls
- "You're X% through the course—keep going!"
- Configurable inactivity threshold
- Motivational without being pushy
Course Upsell
After completing one course, suggest the next. Automated cross-sell at the perfect moment.
- Triggered after a course is completed
- Delay configurable (1 day, 3 days, etc.)
- "Loved that course? Check out..."
- Lower priority: respects member inbox
What the DMs Actually Look Like
These aren't robotic. They feel personal because they are—dynamically filled with each member's name, community details, course info, and more.
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?
Just a heads up—your trial at ends in 3 days.
Here's what you'll lose access to if you don't convert:
• All community discussions and resources
• Upcoming live events and workshops
• Direct access to me and the team
Would love to keep you around. Hit reply if you have any questions!
I noticed you're thinking about leaving . 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.
You just completed — that's a serious accomplishment!
I'd love to hear what your biggest takeaway was. And if you're ready for the next step, check out our advanced course that builds on everything you just learned.
I saw your recent post and wanted to check in personally. It sounds like you might be frustrated with .
I totally get it. Would it help if I walked you through some of the features that might address that? Just reply here and we can set up a quick call.
Custom DM Workflow Builder: Build Anything
Templates not enough? Build unlimited custom DM workflows with our no-code builder. Pick any trigger, add conditions, chain multiple actions with delays.
How the Custom Builder Works
Pick a Trigger
New member joins, someone cancels, trial is ending soon, course completed, member tagged, AI detects churn signal—choose from 15+ event triggers
Add Conditions (Optional)
Filter who receives DMs with simple rules: "Only if member is on a free trial AND joined more than 3 days ago" or "Only if member is Level 3+ OR tagged as VIP"
Chain Actions with Delays
Send DM now → wait 2 days → send follow-up DM → wait 1 hour → tag member → add to CRM → notify team on Slack
Activate and Monitor
Full audit trail: every DM sent, skipped, or failed. Track responses, monitor delivery, and optimize over time.
Example: Trial Member Welcome Journey
Trigger: New member joins
Condition: Only if they're on a free trial
Step 1 (immediately): Send welcome DM — "Welcome, Marcus! Here's how to get started..."
Step 2 (1 minute later): Tag them as "onboarding"
Step 3 (5 minutes later): Add them to HubSpot as a new contact
Step 4 (5 minutes later): Notify your team on Slack — "New trial member: Marcus"
Step 5 (3 days later): Send follow-up DM — "How's Day 3 going?"
Step 6 (7 days later): Send DM — "Here's what you might have missed this week"
Multi-Step DM Sequences (Not Just Single Messages)
Chain multiple DMs with delays to create complete member journeys. Each action can include DMs, emails, tags, CRM updates, and team notifications—all in one workflow.
Welcome Onboarding Sequence
Welcome DM + add to CRM
Check-in DM: "How's it going?"
Resource DM: "Here's what you missed"
Milestone DM: "Congrats on your first month!"
Trial Conversion Sequence
DM: "What brought you here?"
DM: "Have you explored these features?"
DM + Email: "Trial ending soon"
DM + Email: "Last chance to keep access"
Churn Recovery Sequence
DM: "What's not working?" + Slack alert
DM + Email: "Last chance to stay"
Win-back email: "Here's what you're missing"
Final win-back: Special offer
DM + Email Combos: Reach Members on Every Channel
Don't just send a DM. Send a DM and an email. Reach members where they're most likely to see your message.
DM Only
Send a Skool DM only. Best for casual check-ins and community-specific messages.
92% open rate inside Skool
Email Only
Send email via Gmail, SendGrid, Mailchimp, ConvertKit, or Beehiiv. Best for longer content.
Reaches members outside Skool
DM + Email Together
Send both at the same time. Best for critical messages like trial expiry and churn prevention.
Maximum reach for must-see messages
Why DM + Email Combos Matter
DMs have 92% open rates—but some members don't check Skool daily. Emails have lower open rates but reach members outside the platform. For critical messages (trial ending, cancellation), sending both channels simultaneously ensures your message gets seen. StickyHive lets you set the channel per action in your workflow.
How DM Automation Actually Works
Choose Your Trigger
Member joined, trial started, cancellation detected, 3 days before trial ends, or any custom event. Runs on schedule or real-time.
Write Your Message
Write your DM and drop in personalization variables—member's first name, community name, their level, and more. Each message auto-fills with real member data.
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.
It Runs on Autopilot
Messages send automatically. Track every sent DM, skip reason, and member response. Full audit trail.
15+ Event Triggers for DM Workflows
Trigger DMs based on what members actually do—not just time-based schedules. Every event in your Skool community can become a workflow trigger.
Membership Events
Member Joined
Welcome new members instantly
Member Cancelling
Reach out before they leave
Member Churned
Win-back campaigns after departure
Trial Ending Soon
You choose how many days before to trigger
Engagement Events
First Post Created
Boost new member's first post
Member Tagged
Trigger on VIP, at-risk, or custom tags
Member Untagged
Respond when tags are removed
Note Added
Follow up when you add internal notes
AI & Course Events
Churn Signal Detected
AI spots at-risk members before they cancel
Testimonial Detected
AI spots positive testimonials
Course Started
Welcome to the course experience
Course Completed
Celebrate and suggest next steps
Moderation & Support Events
Post Flagged
Auto-respond when posts get flagged
Comment Flagged
Handle flagged comments automatically
Ticket Created
Auto-respond when support tickets come in
Scheduled (Cron)
Time-based triggers: daily, weekly, custom schedules
Dynamic Personalization Variables
Drop these variables into any DM template and they'll automatically fill in with each member's real data. Messages feel personal because they are.
About the Member
- First name → "Marcus"
- Full name → "Marcus Johnson"
- Email address → "marcus@..."
- Skool level → "Level 3"
- Points earned → "1,250"
- Join date → "Jan 15, 2026"
Community & Content
- Community name → "Founders Club"
- Community URL → link to Skool
- Course title → "Growth 101"
- Post title → "My First Win"
- Post link → direct URL
AI-Detected Context
- Detected pain point → "pricing confusion"
- Pain category → "billing"
- Sentiment score → "negative"
- Current date → "Feb 15, 2026"
- Current timestamp → "2:30 PM EST"
Built-In Safeguards (So You Never Spam)
| Feature | How It Protects Members |
|---|---|
| Global Daily Cap | No member receives more than 2 DMs per day across all your workflows combined. If the cap is reached, higher-priority messages (like churn prevention) always get through first. |
| Per-Workflow Limits | Each workflow has its own daily send limit (e.g., max 50 welcome DMs per day). Prevents any single workflow from flooding your members. |
| Cooldown Periods | Don't re-contact the same member within X days (you set the number per workflow, minimum 1 day). Once someone gets a welcome DM, they won't get another one. |
| Granular Opt-Out | Members can opt out of everything, just DMs, just comments, or just likes—their choice. Preferences are respected across every workflow automatically. |
| 5-Level Priority System | Critical messages (welcome, churn prevention) are Priority 1—they always send and get reserved capacity. Conversion and engagement are Priority 2-3. Upsells and win-backs are Priority 4-5 and wait their turn if things are busy. |
| Duplicate Prevention | Built-in locks ensure the same member never receives duplicate messages, even if multiple workflows fire simultaneously. No double-sends, ever. |
| Full Audit Trail | Every action is logged before it sends and updated when it completes. See exactly what was sent, when, to whom, and whether it succeeded or failed—with timestamps and error details. |
| Smart Rate Limiting | Your account has overall sending limits that prevent abuse. Critical workflows get reserved capacity so they always send; lower-priority workflows share the remaining bandwidth. |
All Actions You Can Chain in DM Workflows
DMs are just one action type. Chain DMs with emails, CRM updates, team notifications, tags, notes, and data logging—all in a single workflow.
Messaging
- Send a Skool direct message
- Attach images to your DMs
- Send DM + email at the same time
- Send email only (skip the DM)
- Send as a different team member
CRM Sync
- Add members to HubSpot automatically
- Push to GoHighLevel pipelines
- Sync with ActiveCampaign
- Create contacts in Ontraport
- Trigger CRM workflows on any event
Team Notifications
- Alert your team on Slack
- Send notifications to Discord
- Message your team via Telegram
- Send to custom webhooks
- Real-time visibility for your whole team
Member Management
- Add tags (VIP, at-risk, onboarded, etc.)
- Remove tags when conditions change
- Add internal team notes on members
- Track where members are in their journey
- Segment members for future workflows
Data & Reporting
- Log new rows to Google Sheets
- Track member events in spreadsheets
- Connect to any tool via webhooks
- Full audit trail of every action
- See what was sent, skipped, or failed
Email Marketing
- Send via Gmail or your own email server
- SendGrid for high-volume sending
- Sync members to Mailchimp lists
- Trigger ConvertKit sequences
- Add subscribers to Beehiiv
Multi-Channel by Design: One Workflow, Multiple Actions
A single workflow can: send a Skool DM → wait 5 minutes → send an email → add to HubSpot → tag as "onboarded" → notify team on Slack → log to Google Sheets. All actions chain together with configurable delays (minutes, hours, or days). Build complete member journeys, not just isolated messages.
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. Activate a pre-built template or build a custom workflow in under 5 minutes.
✓ 11+ pre-built DM workflow templates
✓ Custom workflow builder with conditional logic
✓ Multi-step sequences with delays
✓ DM + email combos for critical messages
✓ CRM sync, team notifications, Google Sheets logging
✓ 5-level priority system and built-in safeguards
No credit card • First workflow live in minutes • Cancel anytime
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