Building automated upsell workflows in Mailchimp Journeys for B2B clients

If you’re a B2B marketer or consultant, you know that getting the initial sale is just the start. Upselling—nudging clients to upgrade, add seats, or buy related services—can be a goldmine. But let’s be honest: most B2B upsell emails are either ignored or annoy people. That’s where a smart, automated workflow can actually help.

This guide is for anyone who wants a practical, no-nonsense way to set up automated upsell campaigns in Mailchimp Journeys. You’ll get step-by-step instructions, tips, and some hard truths about what works (and what’s just noise).

Why Bother Automating Upsells in B2B?

Let’s get real: B2B buyers are busy. They don’t want fluffy “upgrade now!” emails in their inbox. But if you time it right—say, after they reach a key milestone, or when their contract is up—automation can do what no manual campaign can: catch them at the perfect moment, with the right nudge.

Automated upsell workflows:

  • Save you time (no more one-off emails).
  • Catch revenue you’d otherwise miss.
  • Make your sales team look good (or keep them out of the loop until someone bites).

But: automation won’t fix a crummy offer or a bad product. And it won’t magically turn cold leads into warm ones. You need to start with a solid reason for someone to upgrade or add on.

Step 1: Clarify Your Upsell Trigger

Before you even log in to Mailchimp, get clear about what will trigger your upsell. This is the most common place people screw up—if you get this wrong, nothing else matters.

Some B2B-worthy triggers:

  • Contract renewal coming up: e.g., 30 days before expiration.
  • Customer hits a usage milestone: e.g., uses 80% of their seats, storage, or API calls.
  • Successful onboarding: e.g., 14 days after a client’s first successful campaign.
  • New feature release: only for customers on lower plans.

What to ignore:
Random date-based triggers (“it’s been 60 days!”) rarely work, unless you have a clear reason for following up. Don’t send upsell emails just because you feel like you should.

Pro tip:
Talk to your sales or support team. They often know the real moments when a customer’s ready for more.

Step 2: Segment Your Audience

Don’t lump all your clients into one list. Intelligent segmentation is what separates useful automation from spam.

Useful segments for B2B upselling:

  • Account size: Small business vs. enterprise (they’ll care about different upsells).
  • Current plan or product: Only upsell what they don’t already have.
  • Engagement level: Active users vs. folks who haven’t logged in for months.

How to set this up in Mailchimp:

  • Use Tags to mark key attributes (e.g., “Pro Plan,” “Basic Plan”).
  • Import custom fields for contract dates, usage, etc.
  • Use Groups for industry or region if your upsell is location-specific.

What to ignore:
Most demographic data (like company size ranges) is too broad for upsells. Focus on behavior and current product.

Step 3: Map Out Your Upsell Journey

Now, sketch your workflow before you touch Mailchimp. This keeps you from building a mess you’ll hate later.

A basic B2B upsell journey might look like:

  1. Trigger: Contract ends in 30 days.
  2. Email 1: “Your renewal is coming up—see what’s new in [Product].”
  3. Wait: 7 days.
  4. Email 2: “Upgrade now and get [incentive].”
  5. Wait: 7 days.
  6. Email 3: “Last chance to lock in your current rate/offer.”
  7. End: Tag as “Upsell Attempted.”

Pro tip:
Less is more. Three emails is usually plenty. Don’t pester people—they’ll just tune you out.

Step 4: Build Your Journey in Mailchimp

Time to put it all together in Mailchimp Journeys:

  1. Create a New Journey:
  2. Go to Automations > Customer Journeys.

  3. Start from scratch or use a template (the “Renewal Reminder” template is a decent starting point, but you’ll want to customize it).

  4. Set Your Entry Point (Trigger):

  5. Use a tag, group, or a custom field (like “Contract End Date”) as your trigger.

  6. For date-based triggers, you’ll need to set up a rule like “30 days before Contract End Date.”

  7. Add Email Steps:

  8. Drag in Email steps after your trigger.
  9. Write clear, benefit-driven subject lines (e.g., “Unlock new features before your renewal”).

  10. Personalize using merge tags (like company name, current plan).

  11. Add Wait Steps:

  12. Space out your emails (usually 5-7 days is good for B2B).

  13. Apply Exit Rules or Tags:

  14. If someone upgrades, tag them so they exit the journey and don’t get more upsell emails.

  15. If not, tag as “Upsell Attempted” for future reference.

  16. Test Your Journey:

  17. Send test emails to yourself and a colleague.
  18. Double-check that triggers and segmentation rules work—Mailchimp’s preview tool is helpful, but don’t trust it blindly.

What to ignore:
Mailchimp’s pre-written upsell content. It’s usually too generic for B2B. Write your own emails.

Step 5: Write Upsell Emails That Don’t Suck

Here’s where most B2B upsell automation falls flat: emails are either too pushy, too vague, or just plain boring.

What actually works:

  • Be direct. “You’re nearing your renewal—here’s what you’ll miss if you don’t upgrade.”
  • Make it relevant. Reference their actual usage or past behavior (“You’ve used 85% of your API calls”).
  • Show clear value. Bullet out the benefits of upgrading, not just features.
  • Offer something real. A discount, extended trial, or free consultation goes further than generic “priority support.”

What doesn’t:

  • Overly casual or “fun” copy (“Ready to level up?!”) — B2B folks usually see right through this.
  • Vague promises (“Unlock your potential!”).
  • Guilt trips or fake urgency.

Pro tip:
Include a clear CTA, but don’t make it the only thing in the email. Sometimes, a secondary CTA (“Talk to sales”) works better for bigger accounts.

Step 6: Measure, Iterate, and Don’t Overcomplicate

You’re not done after launching. Most B2B upsell journeys need tuning.

What to measure:

  • Open rates: If these are low, your subject lines or timing are off.
  • Click rates: If clicks are low, your value prop isn’t clear.
  • Actual upgrades: This is the only metric that really matters.

Iterate by:

  • Testing different triggers (maybe 60 days before renewal works better than 30).
  • Tweaking subject lines and email content.
  • Shortening or lengthening the journey (sometimes one email is enough).

What to ignore:

  • Vanity metrics like “reach” or “impressions.”
  • Overly complex branching journeys. Keep it simple unless you know you need more complexity.

Common Pitfalls (and How to Dodge Them)

  • Triggering too early or too often: People tune out if you upsell before they’re ready.
  • Bad data: If your segmentation fields are wrong or out of date, you’ll send the wrong message to the wrong person.
  • Not excluding recent upgraders: Always set rules to kick folks out of the journey if they buy.
  • Ignoring replies: Sometimes people will actually respond—don’t let those land in a black hole.

Keep It Simple—And Start Small

Automated upsell workflows can absolutely boost B2B revenue, but only if they’re relevant, timely, and respectful. Don’t get sucked into building something complicated just because you can. Start with one or two clear upsell triggers, write a couple of good emails, and see what works. Iterate as you go.

The best upsell journey is the one you’ll actually maintain—and the one your clients don’t mind getting.