If you run support or CX, you already know: waiting for customers to message you is a losing game. By the time they reach out, they're frustrated or halfway out the door. Proactive messaging flips that script—done right, it keeps people engaged, solves problems early, and actually builds loyalty (instead of just talking about it).
This guide is for folks who use Freshchat—or are considering it—and want practical, no-nonsense ways to set up proactive messaging that actually helps keep customers around. I’ll skip the fluff, flag what’s worth your time, and call out what to ignore. Let’s get you set up without the headaches.
Step 1: Get Clear on Why You’re Sending Proactive Messages
Before you dive into settings, ask yourself: What’s the real point of messaging first? If your answer is “Because someone at a conference said it’s good for retention,” hit pause.
Here’s what actually works: - Preventing known issues (billing, outages, shipping delays) - Explaining tricky features or changes before users get confused - Nudging stuck customers back on track (e.g., abandoned carts, incomplete onboarding) - Offering help when you spot warning signs (like a drop in usage)
What to skip:
Don’t spam people with “check out our new blog post!” unless it genuinely helps their workflow. If your message feels like a marketing blast, it’ll get ignored—or worse, annoy people.
Step 2: Map Out Key Customer Moments
Proactive messaging only works if you send it when it matters. Take 15 minutes and jot down: - The points where customers typically get stuck or drop off - Common questions or complaints that come up over and over - Any “red flag” behaviors that signal someone’s about to churn
Examples: - Users who haven’t finished setup in 3 days - Customers about to renew but haven’t logged in for a month - Orders delayed more than 48 hours
This isn’t busywork—it’s the difference between helpful and annoying messages.
Step 3: Set Up Segments & Triggers in Freshchat
Here’s where Freshchat actually shines: it lets you build audience segments and set up automated triggers, so your messages only go to the right people at the right time.
How to do it:
- Create Segments
- In Freshchat, go to Contacts > Segments.
- Build segments based on user behavior, plan, or lifecycle stage. For example:
- “New signups, not completed onboarding”
- “High-value customers, inactive 14+ days”
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Use filters like last seen, plan type, or custom properties.
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Set Up Event-Based Triggers
- Head to Automations > Journeys (or Bots if you’re using them).
- Define triggers: “If user is in ‘Stalled Onboarding’ and hasn’t logged in for 3 days, send message X.”
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You can also trigger based on page visits, actions taken, or inactivity.
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Timing Matters
- Don’t trigger messages the second someone qualifies. Give them a little time—otherwise, it feels robotic.
- Space out repeat nudges. If someone ignores your message, don’t keep hammering them every day.
Pro tip:
Test your segments with small batches before rolling out to everyone. It’s easy to accidentally send the wrong message to the wrong people.
Step 4: Write Messages That Sound Human (Not Like a Bot)
Let’s be real: most proactive messages sound like they were written by a robot. If you want retention, write like a person.
Keep it simple: - Use the customer’s name. - Get to the point in sentence one. - Offer real help, not just a sales pitch. - End with an easy next step (“Reply here if you want a quick walkthrough.”)
Examples of what works: - “Hi Sarah, noticed you haven’t finished setting up your account. Anything I can help with?” - “Heads up: Looks like your last order is delayed. Let me know if you need a status update.” - “Saw you haven’t logged in lately—want a quick refresher on what’s new?”
What to avoid: - “Dear valued user, we would like to inform you…” (Nobody talks like this) - Anything that sounds like a canned promo or marketing blast.
Step 5: Choose the Right Channels
Freshchat lets you send messages via web chat, mobile push, email, WhatsApp, and more. Don’t use every channel just because you can.
Best bets: - Use in-app/web chat for quick tips or onboarding nudges. - Use email for things that need more context, or if they’re not currently logged in. - Use SMS or WhatsApp only for urgent stuff (outages, billing issues)—and only if customers expect it.
What to ignore:
Don’t default to “all channels, all the time.” That’s how you end up in spam folders or blocked.
Step 6: Track What’s Working (and What’s Just Noise)
You’re not done after launching a few messages. Pull reports in Freshchat—check: - Open rates - Response rates (do people reply, or ignore?) - Actual retention metrics (did your outreach move the needle on churn or repeat usage?)
If a message gets ignored:
Tweak the copy, try a different timing, or just kill it. No shame in cutting what doesn’t work.
If customers reply with “stop” or “unsubscribe”:
You’ve crossed the line. Dial it back.
Pro tip:
Ask your support team what messages get good replies (or complaints). The folks on the front lines hear what works and what ticks people off.
Step 7: Don’t Go Overboard—Less Is More
It’s tempting to set up a dozen automated messages and call it “customer engagement.” Resist that urge.
- Start with one or two key moments (like onboarding or renewal)
- Watch how they perform
- Add more only if you see positive results
Remember: one helpful ping is better than a dozen pointless nudges.
Step 8: Keep the Opt-Outs Obvious
Don’t make customers hunt for a way to mute proactive messages. Always include a “let us know if you don’t want these” option in your copy, or use Freshchat’s built-in unsubscribe features.
It’s not just about compliance—it’s about trust.
What Actually Moves the Needle (and What Doesn’t)
Worth your time: - Messages that genuinely prevent a problem or answer a common question before it’s asked - Timely nudges tied to real user behavior
Mostly noise: - Generic “check out our latest update!” messages - Over-personalized stuff that feels creepy (“We saw you clicked on the pricing page 5 times yesterday…”)
Flat-out bad: - Anything sent too frequently, or to the wrong segment
Wrapping Up
Don’t overcomplicate this. You don’t need a “proactive messaging center of excellence”—you just need a few useful, well-timed messages that sound like you actually care. Start simple, watch the data, and adjust from there. If a message feels annoying to you, it’s probably annoying to your customers, too.
Less noise, more real help. That’s what keeps people coming back.