Tips & Tricks from the OrangeMage Spellbook
Workflows are one of HubSpot’s most powerful tools, but when it comes to enrollment triggers, the path isn’t always straightforward. What seems obvious in your head can hit a wall in practice, leaving you staring at grayed-out options or puzzling error messages.
At OrangeMage, we’ve seen these obstacles countless times. That’s why we’ve pulled together a set of tips and tricks for tackling the less-obvious sides of workflow enrollment. From re-enrollment loops, to clever “Dippy Bird” properties, to association tracking with rollups, these are the spells we keep in our back pocket when HubSpot says “no” but the business need says “yes.”
Why This Matters (and Where AI Helps, But Not Always)
Yes, HubSpot’s new AI workflow trigger helper makes things easier, but it won’t always get you exactly what you want. And sometimes, what you want just isn’t possible inside the standard workflow tool. That’s why we’re cataloging these “simple solves” here, so you can keep crafting with confidence.
Re-Enrolling on Potential Loops (Without Summoning Chaos)
HubSpot does its best to protect us from infinite loops. I didn’t appreciate this safeguard until I accidentally sent a co-worker 40,000 emails while she was on vacation, which was just enough to drain her battery completely. Oops... Deep down, I think she probably enjoyed the freedom.
....Anywhozle....
Sometimes you actually do want people to re-enroll, and HubSpot blocks you. The fix? Use a segment (formerly known as a list).
✨The Solve
-
Build a segment using the same criteria you wanted to use for workflow enrollment.
-
Instead of enrolling directly, set your workflow trigger to “List Membership.”
This clever detour bypasses HubSpot’s wall, while still giving you control.
The Dippy Bird Property (A Self-Resetting Trigger)
Named after those bobbing birds that keep dipping their beaks into water, this trick creates a repeatable, structured motion inside your workflows.
Use Case Example: Running a loyalty program and sending recurring reminders.
✨ Conjure the Dippy Bird
-
Create a custom date property: Date Last Loyalty Reminder.
-
At the end of your workflow, set this property to today’s date.
-
Build a segment: Date Last Loyalty Reminder is more than X days ago.
-
Use that segment as your enrollment trigger.
🎁 Bonus Tip: You can make sure this only runs on weekdays (or a specific day of the week) using workflow settings. Perfect for campaigns that shouldn’t hit inboxes on Sunday at midnight.
Tracking Association Changes with Rollup Properties
This is more advanced magic; less common, but critical if you’re managing data across multiple objects.
The Problem: HubSpot doesn’t let you trigger workflows when associations change. Whether it’s:
-
A new deal linking to a company,
-
A contact picking up a new subscription, or
-
(For fantasy fans) Tim the Enchanter adopting a new goat 🐐 (or, tragically, losing one)…
Workflows just don’t see the association shift.
The Fix: Rollup properties.
✨ See the Hidden Association Changes
-
Create a rollup property of type Sum.
-
Point it at the object you’re tracking.
-
Select the Record ID field as the value to roll up.
-
(Optional) Add filters to narrow what you’re tracking.
When associations change, the rollup’s value changes too—giving you a magical “signal” you can use.
From there, just set your workflow to enroll when this property is known with re-enrollment enabled.
Wrapping Up
As we continue connecting with more users and exploring additional accounts, we’re always discovering new opportunities for workflow optimization. Until our next update, we hope these tips serve you well. If you encounter challenges that require more than a dash of practical magic, don’t hesitate to reach out. We’re here to help and happy to schedule time to talk through your toughest workflow puzzles.