Relay Software: Three Workflows, One Inbox Disaster
Relay Software sells a $180/month project tool. Marketing runs two contact workflows: 'Demo Request Follow-Up' (5 emails over 12 days, trigger is submission of the demo form, re-enrollment switched on) and 'Free Trial Nurture' (9 emails over 30 days, trigger is lifecycle stage equals Trial). A quarterly promotion workflow, '20% Off Upgrade', triggers on any contact whose trial end date falls within 14 days. Last month 830 trial users received nurture email #6 and the promotion email on the same day; 340 recipients were existing paying customers who had opened a second trial workspace; 47 contacts received the demo follow-up sequence twice within a month after re-submitting the form; and 2,100 contacts who had opted out of the Promotions subscription type still received the discount email, because that email was set to the Marketing Information type. There is no suppression list anywhere, and none of the three workflows has a goal defined.
1. Diagnose why the collisions happened and restructure the automation so they cannot recur.
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Root cause is architectural, not copywriting. HubSpot allows a contact to be enrolled in multiple workflows at once, so three workflows with overlapping audiences will collide by design. Nothing coordinates them: no suppression list, no goal criteria, no branch that checks whether the contact is already a paying customer.
Restructure:
- Add one suppression list per state that should never receive acquisition messaging: 'Active Customers' (lifecycle stage = Customer or an active subscription property), 'Open Opportunities', and 'Recently Contacted (7 days)'. Attach it as a suppression list to every acquisition workflow rather than remembering to filter inside each one.
- Define goals so contacts exit on success, not on the end of the sequence. Demo follow-up: goal = meeting booked or lifecycle reaches Opportunity. Trial nurture: goal = subscription activated.
- Add a branch or an if/then at the top of the promotion workflow: if lifecycle is Customer, route to an expansion path or unenroll.
- Stagger timing: the promotion email should not be able to land on the same day as nurture email #6. Either suppress the nurture for contacts in promotion, or add a one-day send delay and a 'received email in last 48h' check.
Test before re-enabling by sending to an internal list and checking the contact timeline for simultaneous sends.
2. The demo follow-up workflow has re-enrollment on. What are the consequences and how would you decide whether to keep it?
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What re-enrollment does. With it on, any contact who submits the demo form again re-enters the workflow at step one, resets their position, and can receive the entire five-email sequence again - 47 contacts did exactly that within a month. It also restarts the sequence for someone who is mid-conversation with a rep, which reads as a broken CRM to the buyer.
Decision framework - is re-entry a real state change? Re-enrollment is right when the trigger represents a genuinely recurring event and the message is still true the second time: registering for a different webinar, or requesting a demo after a six-month gap. It is wrong when the trigger is the same action repeated within a short window, or when the contact's state has since changed (they already booked a meeting, they already bought).
Recommendation. Turn re-enrollment off for the five-email sequence and create a short, separate 'Second Demo Request' workflow - two emails, different copy, enrollment capped to once per 90 days. That preserves the signal without the repetition. Add a goal of meeting booked so anyone who converts exits immediately, and add the Active Customers suppression list so a customer who submits the form goes to an account-management path instead of a sales pitch.
Monitor: count of contacts enrolled more than once per quarter, and unsubscribes on step two, which is where repetition damage shows first.
3. 2,100 contacts received a discount email after opting out of Promotions. Explain the mechanism and the fix, and say what else subscription-type misconfiguration can break.
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Mechanism. Unsubscribing is per subscription type, not global, unless the contact uses the global unsubscribe link. A contact who opts out of Promotions remains marketable for Marketing Information, and the discount email was set to the wrong type - so the send respected the type it was assigned, not the preference the contact expressed. It is one of the most common compliance-adjacent bugs in HubSpot because it is a per-email setting that nobody audits.
Fix. Audit the subscription type on every promotional email and default new marketing emails to Promotions, with the type set at template level so it cannot be forgotten per send. Make Marketing Information genuinely informational - product updates, service notices - not a back door for offers. Add a pre-send check: for any offer email, confirm the type matches the offer and that the opt-out list for that type is excluded.
What else breaks. Transactional emails (receipts, password resets, trial expiry notices) should have their own type so unsubscribing from marketing does not silence account-critical mail. Conversely, if trial-expiry warnings sit under Promotions, contacts who opted out stop being warned and then complain at conversion. And reporting: open and click rates by subscription type are meaningless if types are assigned arbitrarily, which quietly corrupts any dashboard built on them.