8 HubSpot Slack Workflows Every CS Team Needs to Reduce Churn in 2026

Customer Success Managers are responsible for ensuring customers achieve their goals, stay healthy, renew their contracts, and expand their usage. The average CS Manager is juggling 50-100+ customer accounts simultaneously.

Here's what happens: You're focused on active deals and loud customers while quiet ones slip through the cracks. Someone stops logging in. Usage drops 40%. And you don't notice until they mention they're "exploring other options." By then it's too late. Manually monitoring 75+ health scores, engagement patterns, and renewal dates while doing actual CS work is impossible.

This is where HubSpot Slack workflows change everything for CS teams.

In this guide, we'll walk through 8 workflows that top CS teams use to catch churn risks early, drive expansion revenue, and turn customer retention into a system instead of daily chaos.

But before we dive into workflows: if you're using Slack Connect to talk to customers, Sidekick's Auto-Log Slack feature might be worth checking out. It automatically captures those conversations and logs them to HubSpot.

What Are HubSpot Slack Workflows (And Why CS Teams Need Them)

Traditional HubSpot Slack integrations send notifications. You read the alert, then open HubSpot to do something about it. You're still switching contexts.

Bi-directional workflows are different. They bring your customer data into Slack AND let you take action without ever opening HubSpot. Update customer status, flag at-risk accounts, create follow-up tasks, and add notes documenting what you're seeing. All with button clicks in Slack.

This is how CS teams automate customer health monitoring in HubSpot without checking dashboards all day.

For CS teams managing 50-100 accounts, this means:

• Churn signals don't hide: Workflows catch health drops, engagement gaps, and renewal risks before they become emergencies

• You act in hours, not days: When someone stops engaging, you respond immediately

• Expansion windows stay open: Usage growth signals get caught while customers are actively scaling

CS teams using workflow automation save 8-12 hours per week on customer monitoring. They redirect that time to actual relationship building.

We built Sidekick's bi-directional workflow system to solve exactly this problem. It works with HubSpot's four main objects (Contacts, Companies, Deals, and Tickets) so CS teams can monitor everything that matters. You can set up any of these workflows in under 10 minutes.

Let's dive into the 8 workflows that make this possible.

1. Customer Health Score Drop Alert

The CS Challenge

A customer's health score drifts from 85 to 75 over two weeks. Then 75 to 65. Then 65 to 52. But no one notices because you're busy with the 40 other accounts on your plate. By the time you catch it (usually during your monthly check-in when they mention they're "evaluating alternatives"), you have days, not months, to salvage the relationship.

How the Workflow Works

This workflow triggers when a customer's health score property drops below your defined threshold. Typically a 15-20 point drop or falling below 60 out of 100.

You receive a Slack DM:

"⚠️ Health Alert: [Customer Name] health score dropped from 85 to 58"

For each alert, you see:

• Customer name and current health score

• What's driving the decline (usage drop, support tickets, low engagement)

• Days since last meaningful interaction

• Contract value and renewal date

Action buttons let you respond immediately:

• "Flag as At-Risk" - Updates customer status property

• "Add Note" - Log what you're seeing and next steps

• "Create Task" - Schedule health check call

• "Assign to Senior CSM" - Updates owner property to escalate

Everything you click updates HubSpot automatically.

Real Impact for CS Teams

• Early intervention: Catch problems 6-8 weeks earlier than quarterly reviews

• Higher save rates: Addressing concerns at health score 60 vs. 30 dramatically improves outcomes

• Less stress: No more discovering critical issues during renewals

One Sidekick customer reported catching churn risks an average of 47 days earlier after implementing health score alerts. Those extra weeks translated to a 34% improvement in save rates.

Ready to catch churn risks early? Learn more about health monitoring workflows →

2. No Activity in 14 Days - Engagement Alert

The CS Challenge

The most dangerous customers are the quiet ones. They don't complain. They don't reach out for help. Everything seems fine on the surface. But they stopped logging in three weeks ago, and you don't notice until renewal time when you learn they moved to a competitor eight weeks ago.

How the Workflow Works

This workflow uses time-based filters to identify customers with no logged activity for 14+ days while their status is still "Active."

Every Monday at 9 AM, you receive a Slack message:

"🔕 Engagement Alert: 4 customers haven't had any activity for 14+ days"

For each customer, you see:

• Customer name and days since last activity

• What their last interaction was (meeting, email, support ticket, product login)

• Health score and contract value

• Renewal date (if approaching)

Quick action buttons help you re-engage:

• "Flag as Low Engagement" - Updates health score component property

• "Add Note" - Log the situation and your plan

• "Create Task" - Schedule check-in call

• "Enroll in Sequence" - Add to re-engagement email sequence

Real Impact for CS Teams

• Catch disengagement early: Identify quiet customers while there's still time to reconnect

• Reduce silent churn: Many quiet customers are just busy. A timely reach-out reignites engagement.

• Build systematic habits: Weekly check-ins become automatic

CS teams using engagement alerts reduce silent churn by 23% on average.

Never let a customer go silent again. Set up engagement monitoring →

3. Support Ticket Volume Spike

The CS Challenge

You get a support ticket notification. Then another. Then three more. All from the same customer over three days.

Is this a product bug that's about to cause churn? Or is it a sign they're expanding usage and hitting complexity walls? Either way, it's a CS moment. But most CSMs don't see ticket patterns until someone from support mentions it in passing a week later.

How the Workflow Works

This workflow monitors the HubSpot Tickets object and triggers when a customer account hits defined thresholds: 3+ open tickets simultaneously OR 5+ tickets created within 7 days.

You receive an immediate Slack alert:

"⚠️ Ticket Spike: [Customer Name] has opened 5 tickets this week"

For each alert, you see:

• Ticket volume and trend comparison

• Ticket subjects and themes (bug reports? feature requests? how-to questions?)

• Severity levels and current status

• Whether this is unusual for this customer

Action buttons let you triage appropriately:

• "Update Status" - Flag as "Support Escalation" or "Expansion Opportunity"

• "Add Note" - Document the ticket pattern and your assessment

• "Create Task" - Schedule proactive call with customer

• "Assign to Product Team" - Update owner to loop in engineering

Real Impact for CS Teams

• Turn problems into opportunities: Proactive CSM outreach transforms support experiences

• Identify expansion signals: High ticket volume sometimes means growth, not dissatisfaction

• Reduce support-to-churn conversion: Catch frustration before it escalates

One Sidekick customer reduced support-to-churn incidents by 34% simply by having CSMs call customers within 24 hours of ticket spikes.

Get alerted to support patterns. Learn about ticket spike workflows →

4. New Customer Onboarding Kickoff

The CS Challenge

A deal closes. The sales team celebrates. The customer is excited. Then... silence.

Two days pass. Then three. The customer starts wondering: "Did they forget about me?" Meanwhile, you're busy with existing customers and don't even know the new customer exists yet. By the time the handoff happens five days later, excitement has turned to doubt.

How the Workflow Works

This workflow triggers the instant a deal reaches "Closed Won" status or when the Deal Type property equals "New Business."

You receive an immediate Slack notification:

"🎉 New Customer: [Company Name] just signed - $50K ARR"

For each new customer, you see:

• Company name and contract details (ARR, contract length)

• Who sold the deal and any handoff notes

• Expected use case and goals from the sales process

• Team size and anticipated go-live date

Action buttons eliminate handoff delays:

• "Assign to Me" - Updates CSM owner property

• "Update Status" - Change to "Onboarding - Kickoff Scheduled"

• "Create Task" - Schedule kickoff call within your SLA

• "Enroll in Sequence" - Add to welcome email sequence

Real Impact for CS Teams

• Zero handoff delays: Customers receive kickoff outreach within 24 hours

• Higher onboarding completion: Fast kickoffs lead to 2.7x higher completion rates

• Faster time-to-value: Immediate engagement reduces time-to-value by 18 days on average

Perfect your onboarding handoff. See how new customer workflows work →

5. Onboarding Milestone Tracking

The CS Challenge

Customer onboarding has clear milestones: first integration complete, team training done, initial workflows configured, first success metric achieved. But without tracking, you have no idea if customers are on pace, stuck, or racing ahead.

The result? Some customers fly through onboarding in three weeks. Others stall at "first integration" for six weeks without anyone noticing.

How the Workflow Works

This workflow triggers whenever custom onboarding milestone properties update in HubSpot: "First Integration Complete" = Yes, "Team Training Done" = Yes, "Success Criteria Defined" = Yes, etc.

You receive a celebration message:

"🎯 Milestone Hit: [Customer Name] completed their first integration! (Day 15 of onboarding)"

For each milestone, you see:

• Which milestone was achieved

• Days since onboarding kickoff

• Remaining milestones and typical timeline

• How this customer's pace compares to average

Action buttons maintain momentum:

• "Update Milestone Status" - Mark as complete in HubSpot

• "Add Note" - Acknowledge the achievement and document next steps

• "Create Task" - Schedule progress call if needed

• "Enroll in Sequence" - Send next milestone guidance email

Real Impact for CS Teams

• Celebrate wins: Acknowledge progress, build momentum

• Catch stuck customers: Identify blockers before they derail onboarding

• Reduce time-to-value: Tracking reduces average TTV by 18 days

• Improve completion rates: Visibility increases onboarding completion from 67% to 89%

Track onboarding systematically. Learn about milestone workflows →

6. Renewal Kickoff (90 Days Before Contract End)

The CS Challenge

Most CS teams start renewal conversations 30-45 days out. At that point, if the customer has concerns (about pricing, product gaps, ROI, or anything else), there's barely time to address them. Let alone position upsells or conduct an executive business review.

Renewals become transactional and stressful. You're operating on their timeline, not yours.

How the Workflow Works

This workflow triggers 90 days before contract end date for any deal where Deal Type = "Renewal" or based on custom contract end date properties.

You receive a Slack alert:

"⏰ Renewal Runway: [Customer Name] contract ends in 90 days - $50K ARR at stake"

For each upcoming renewal, you see:

• Customer name and contract value

• Renewal date and days remaining

• Current health score and 90-day trend

• Usage patterns over the past quarter

• Support ticket summary

Action buttons kickoff renewal planning:

• "Update Stage" - Move deal to "Renewal - In Progress"

• "Add Note" - Document renewal strategy and concerns

• "Create Task" - Schedule QBR with customer

• "Flag Concerns" - Update property to escalate known risks

Real Impact for CS Teams

• Strategic renewals: Transform transactions into partnership conversations

• Higher upsell rates: 90-day runway enables expansion positioning (23% lift)

• Faster renewal cycles: Decisions happen faster when you start early (41% faster)

• No surprises: Never walk into a renewal and discover the customer has been unhappy for months

Start renewals the right way. Set up renewal tracking →

7. Upsell/Cross-sell Opportunity Signal

The CS Challenge

The best expansion opportunities hide in usage data. A customer's active users grow 45% this quarter. A company just raised a Series B. A team is hitting seat limits.

But you miss these signals because they're scattered across product analytics, HubSpot properties, and casual conversation snippets. By the time you notice the expansion potential, the moment has passed.

How the Workflow Works

This workflow triggers when usage or firmographic indicators signal expansion potential:

• "Active Users" property grows by 40%+ (signals increased adoption)

• "Seats Used" approaches "Seats Purchased" (signals need for more capacity)

• Company properties update (headcount growth, revenue increases, funding rounds)

You receive a Slack alert:

"📈 Expansion Signal: [Customer Name] active users up 45% this month"

For each signal, you see:

• What metric changed and by how much

• Trend over time (sudden spike or steady growth?)

• How close they are to product limits

• New use cases emerging from support tickets or feature requests

Action buttons help you capitalize:

• "Update Property" - Flag as "Expansion Opportunity"

• "Add Note" - Document the usage growth and opportunity size

• "Create Task" - Schedule expansion conversation call

• "Enroll in Sequence" - Add to upsell nurture campaign

Real Impact for CS Teams

• Higher NRR: Capture expansion while customers are actively growing

• Faster expansion cycles: Reduce median time from signal to closed deal from 94 to 47 days

• Better timing: Catch buying signals while they're still relevant

Capture expansion revenue systematically. Learn about expansion workflows →

8. At-Risk Renewal Alert (30 Days Before Contract End)

The CS Challenge

Despite your best efforts, some renewals enter the final 30 days with red flags everywhere. Low health score. Minimal engagement over the past month. Unresolved support tickets. Executive sponsor changed and you haven't built a relationship with the new one.

At this point, standard CS motions won't work. You need emergency protocols, executive escalation, and decisive action. But most CS teams don't have systems to treat at-risk renewals differently from healthy ones. So they get the same automated "renewal coming up!" email at the same time.

How the Workflow Works

This workflow triggers when multiple risk factors align within 30 days of renewal:

• Deal Close Date < 30 days away AND

• Health Score < 60 OR

• Last Activity > 30 days OR

• Open critical support tickets

You receive an urgent Slack alert:

"🚨 URGENT: [Customer Name] renewal in 28 days - Health Score 45/100"

For each at-risk renewal, you see:

• Contract value in jeopardy

• Specific risk factors (low usage, support issues, pricing objections, champion changes)

• Recent interaction history

Action buttons enable emergency response:

• "Update Status" - Flag renewal as "At Risk - Urgent"

• "Add Note" - Document all risk factors and save plan

• "Create Task" - Schedule executive save call

• "Assign to VP CS" - Escalate owner for senior involvement

Real Impact for CS Teams

• Last-chance interventions: Give at-risk renewals appropriate urgency

• Executive alignment: Ensure senior leaders engage on critical accounts

• Save rate improvement: Recover 1-in-4 customers who would otherwise churn

Teams using at-risk renewal alerts save an average of $47K per recovered account.

Catch at-risk renewals before it's too late. Learn about renewal risk workflows →

Getting Started: Which Workflows Should You Implement First?

You don't need to implement all 8 workflows at once. Start with the 2-3 that address your biggest pain points:

If your biggest challenge is churn prevention:

Start with:

1. Customer Health Score Drop Alert (#1)

2. No Activity in 14 Days (#2)

3. At-Risk Renewal Alert (#8)

These three create an early warning system that catches problems before they become emergencies.

If your biggest challenge is proactive engagement and onboarding:

Start with:

1. New Customer Onboarding Kickoff (#4)

2. Onboarding Milestone Tracking (#5)

3. No Activity in 14 Days (#2)

These workflows ensure smooth handoffs, systematic onboarding progression, and no customer falls through the cracks.

If your biggest challenge is revenue retention and expansion:

Start with:

1. Renewal Kickoff 90 Days Out (#6)

2. Upsell/Cross-sell Signals (#7)

3. At-Risk Renewal Alert (#8)

These workflows turn renewals from reactive transactions into strategic revenue opportunities.

Workflow automation compounds. Each workflow you add makes your day a little easier, your customers a little healthier, and your retention metrics a little better.

The Bottom Line: Focus on Customers, Not Dashboards

Customer Success professionals didn't sign up to be dashboard monitors. You became a CSM to help customers succeed and build real relationships.

These 8 workflows give you that time back. They eliminate the constant dashboard checking, the forgotten follow-ups, the panic when you realize someone's been quiet for three weeks, and the stressful renewals that could have been prevented months earlier.

The result? You spend less time monitoring systems and more time doing what you do best: helping customers win.

Ready to transform how you work?

Try Sidekick free - set up your first workflow in less than 5 minutes. No credit card required. Or book a personalized demo to see these workflows in action and discuss which ones would have the biggest impact on your team's retention metrics.