Proactive Chat Triggers Playbook

Condition: On the pricing page for [30] seconds, or scrolled past the plan comparison.

Do not fire if: the visitor already started checkout, or this trigger fired earlier today.

Opening message: Picking a plan? Happy to help you figure out which one fits [team size / monthly volume].

Follow-up if they reply: Quick question, are you mostly comparing on price or on the [specific feature]? That usually decides it.

If they ask about discounts: We can talk through annual billing and any options for [startups / nonprofits]. Want me to pull that up?

Fallback if no reply in [20] seconds: No rush. I will leave this open if a question comes up.

Condition: Items in cart and no progress for [45] seconds, or the visitor reopened the cart twice.

Do not fire if: a payment attempt is in progress, or the order already completed.

Opening message: Stuck at checkout? Happy to sort out anything with shipping, payment, or a code that is not applying.

If they mention a coupon issue: Drop the code here and I will check whether it is active for [your cart / your region].

If they mention shipping cost: Want me to show the options for [destination]? Some are faster, some are cheaper.

Soft exit: Need a minute? Totally fine. I am here when you are ready to finish up.

Condition (desktop): Mouse moves toward the browser top bar or back button on [pricing / product / signup] pages.

Condition (mobile / touch): No cursor exists, so use a touch-equivalent signal instead, like a fast scroll back to the top followed by [3] seconds of inactivity, or a detected back gesture, on those same pages.

Do not fire if: the visitor already messaged you this session, or they are on a confirmation page. On touch devices, do not fire on the cursor-only rule, since it never triggers there.

Opening message: Before you go, did you find what you were looking for?

If they were comparing options: Want a short summary of [plan A vs plan B] by email or [WhatsApp], if you share where to send it? That way you have it for later.

If they hit a blocker: What got in the way? Even a one-word answer helps me point you in the right direction.

Capture line: Want me to save your spot? Leave a [name and email or WhatsApp number] and I will follow up, no spam.

Setup note: This capture and channel switch both need the visitor to opt in with a contact handle, which lands in [your CRM] for follow-up, so connect it first or there is nowhere to save the lead.

Setup filter: Skip this trigger on thin pages under [300] words, since there is not enough to engage with there.

Condition: On a [feature / integrations / demo] page for [40] seconds with active scrolling.

Do not fire if: the visitor is clearly skimming and leaving fast, or this trigger already fired for them today.

Opening message: Reading up on [feature name]? I can answer anything specific or show you how it works with [your tools].

If they ask how it works: Tell me your setup and I will walk through the exact steps for [your case].

If they want to see it live: Want a quick [demo / call] booked, or should I just answer right here? Whichever is easier.

Channel offer: Prefer to continue on [WhatsApp / Telegram / Instagram]? Reach out from there and I will pick it up, so I have a handle to reply to.

Setup note: This trigger needs visitor history and open-ticket status from your CRM or helpdesk, so wire up [your CRM / helpdesk] first or it has nothing to read.

Condition: A repeat visit within [7] days, or a logged-in or previously identified contact returns.

Do not fire if: the last conversation ended under [1 hour] ago, or there is an open human ticket.

Opening message: Welcome back. Want to pick up where we left off on [last topic], or is this something new?

If they had an open question: Last time you asked about [topic]. Did that get sorted, or should I dig in?

If they are further along now: Looks like you are closer to a decision. Want me to line up [next step] for you?

Personalized nudge: I still have your notes on [need / use case], so we can skip the intro and get to it.

Setup note: The escalation line below hands off to a human, so connect [your CRM / helpdesk] for ticket routing or there is no team inbox to pass them to.

Condition: On a [help / docs / troubleshooting] article for [60] seconds, or the same article opened twice.

Do not fire if: the visitor came from a successful action, or they dismissed this trigger today.

Opening message: Stuck on this one? Tell me what you are trying to do and I will give you the short version.

If they describe an error: Paste the exact message or screenshot and I will tell you what it means and the fix.

If it is a feature request, not a bug: Got it, that is not built in yet. I will log it for the team [and follow up if you leave an email].

Escalation line: This looks like one for a human on our team. Want me to hand you off now or set up a callback?