If you're in B2B sales and dealing with enterprise prospects, you already know that canned, spray-and-pray messages don’t get replies. You need to follow up—thoughtfully, personally, and at the right moments. The trick is doing it without drowning in manual work or coming off like a robot.
This guide is for sales pros, marketers, and anyone who wants to set up personalized follow-up sequences in Manychat that actually help move enterprise deals forward. I'll show you how to build sequences that feel human, make sense for complex sales, and don’t burn bridges with bad automation.
Let’s cut the fluff and get into the nuts and bolts.
Why Most Automated Follow-Ups Flop (Especially for Enterprise)
Before you build anything, a reality check: Most follow-up automations are ignored or deleted. Here’s why:
- Over-automation: Prospects can spot a generic sequence a mile away.
- Lack of context: Enterprise deals are rarely one-size-fits-all. Automation that ignores deal stage or stakeholders will flop.
- Wrong channel: Manychat is built for chat messaging (think Facebook Messenger, Instagram, WhatsApp, SMS). If your enterprise prospects only live in email, don’t force-fit chat just because it’s shiny.
That said, when done right, Manychat sequences can help you nudge deals forward—if you keep it personal, contextual, and respectful.
Step 1: Get Clear on Your Goals & Audience
Don’t skip this. If you automate without a plan, you’ll annoy people and waste your time.
Ask yourself:
- What action do I really want? (Book a meeting, get a reply, share info, etc.)
- Where do my enterprise prospects actually communicate? (Messenger, SMS, Instagram DMs, WhatsApp?)
- What’s their buying process like? (How many stakeholders, how long is the cycle, what info do they need?)
Pro tip: If your prospects hate chatbots, don’t force it. Manychat works best when there’s already some buy-in to messaging channels.
Step 2: Segment Your Prospects (Don’t Treat Them All the Same)
Blanket sequences don’t cut it for enterprise. You need to segment.
Ways to segment in Manychat:
- By company size: “Enterprise” means different things. A 500-person firm isn’t the same as a Fortune 100.
- By stage: Early interest vs. mid-funnel vs. legal/procurement.
- By persona: Technical, economic, or end-user buyer.
How to do it in Manychat:
- Use custom fields for company name, deal stage, and role.
- Tag prospects based on their responses or how they entered your funnel.
- If integrating with your CRM, sync fields so you always have the latest info.
Why this matters: Your messages should reference their company, role, and stage. That’s what makes it feel personal, not robotic.
Step 3: Map Out Your Follow-Up Sequence (On Paper First)
Don’t start building in Manychat yet. Sketch your sequence first.
Key questions to answer:
- How many follow-ups will you send?
- What’s the timing between them? (Don’t be the daily spammer.)
- What’s your escalation path if you don’t get a reply? (Escalate to a human? Try a different channel?)
- What content actually helps at each stage? (Case study, demo video, invite to call, etc.)
Keep it short: Enterprise buyers are busy. Three to four touchpoints is usually plenty.
Step 4: Personalize Your Messages—But Don’t Fake It
The fastest way to lose trust is to pretend your message is manual when it’s clearly automated. Use personalization only where you actually have the data.
In Manychat, you can:
- Insert custom fields like {First Name}, {Company Name}, or {Role}.
- Reference previous interactions (“You mentioned X in our last chat…”).
- Trigger different flows based on how they responded before.
What to avoid:
- Don’t overdo the {First Name} trick—people see through it.
- Don’t make up details if you don’t have them.
- Don’t pretend to be “checking in” if it’s just scheduled spam.
Sample message:
Hi {First Name}, just wanted to follow up on our discussion about {Relevant Topic}. If you still have questions about how we help {Company Name} with {Pain Point}, happy to jump on a quick call.
If you can’t fill in the blanks honestly, don’t send the message.
Step 5: Build Your Sequence in Manychat
Now it’s time to get your hands dirty.
Create a Flow
- In Manychat, go to Automation > Flows.
- Start a new Flow for your enterprise follow-ups.
- Map out each message as a step in the Flow.
Add Personalization
- Use Dynamic Fields for names, company, etc.
- Add Conditions to branch the flow based on responses or tags.
Set Timing
- Use the “Delay” step to space out messages (e.g., 2–5 days between follow-ups).
- Don’t go overboard—spamming daily isn’t smart.
Handle Replies
- Always give a clear way for prospects to reply, ask questions, or opt out.
- Use “Smart Delay” or “If/Else” logic to change the sequence if they respond.
- If you get a positive reply, trigger a human handoff (e.g., notify your sales team).
Integrate with Your CRM (if possible)
- Use Manychat’s native integrations, Zapier, or webhooks to sync with Salesforce, HubSpot, etc.
- Update lead status, notes, or other fields automatically.
- This helps keep your data clean and avoids double-messaging.
Pro tip: Test the entire sequence on yourself and a teammate before going live. Watch for awkward phrasing, timing issues, or broken logic.
Step 6: Don’t Set It and Forget It—Monitor & Improve
Automation is not magic. If you aren’t tracking replies (and drop-offs), you’ll never know what’s working.
What to watch:
- Open/read rates (if the channel supports it)
- Reply rates and positive responses
- Where prospects drop off or get annoyed
What to ignore:
- Vanity metrics like “messages sent” or “sequence completed” don’t matter if you aren’t getting real engagement.
How to improve:
- Tweak timing (are you following up too soon or too late?)
- Rewrite messages that get ignored
- Cut steps that aren’t adding value
Pro tip: Ask a friendly customer or colleague to review your messages. If they cringe, so will your prospects.
Real Talk: What Works (and What Doesn’t)
Works:
- Short, direct, personalized messages
- Clear next steps (not just “checking in”)
- Opt-out options (respect people’s time)
- Integrating with CRM so you don’t double-message
Doesn’t Work:
- Overly clever or “funny” bots (keep it professional)
- Sending too many messages
- Ignoring replies or not handing off to a real person when asked
- Treating enterprise deals like low-ticket e-commerce
Ignore:
- “AI-powered personalization” that’s just mail merge
- Any vendor promising “10x replies overnight”
Quick Troubleshooting
- Not getting replies? Your message might be too generic, too frequent, or hitting the wrong pain point.
- Getting opt-outs? Rethink your timing. Maybe your prospects don’t want messages on that channel.
- Breaking things in Manychat? Start simple. Don’t get lost in crazy logic before you’ve proven your sequence works.
Keep It Simple and Iterate
Don’t try to automate your entire enterprise pipeline on day one. Start with one or two touchpoints for a single segment. See what works, then add complexity if (and only if) you need it.
Remember: The goal is to help your prospects, not just “move them through a funnel.” Personalization is about respect, not just using their first name.
Set up your first sequence, test it, and keep tweaking. That’s how you’ll actually see results—with a lot less busywork.