Mailchimp Trial Onboarding & Lifecycle Automation

RecMan is an Oslo-based applicant tracking and workforce management platform serving recruitment agencies and in-house talent teams across Norway and beyond. The company offers three product tiers, from a standalone ATS to a full recruitment CRM to a complete workforce management suite covering staffing, time tracking, and payroll. As RecMan grew its trial-based signup model across all three tiers, they needed an email system that could nurture prospects through their free trial period and route them cleanly into either the customer base or ongoing lead follow-up, without adding manual work for the sales team.

The Challenge 

RecMan offers three product tiers (ATS, Recruiter, Workforce), each with its own 14-day free trial. Their Mailchimp instance needed email automations that could welcome trial users, encourage them to engage with resources and sales staff, and then separate converted customers from those who didn't convert, all without manual intervention from the sales team.

The existing contact list also needed cleanup and proper segmentation before any automation could run reliably.

The Approach

I led the strategy, tagging architecture, and segmentation logic, then built it out in Mailchimp.

Contact segmentation and list cleanup
Audited and reorganized the existing contact database, building a tagging structure that could track trial status, plan tier, and conversion state without creating duplicate or conflicting segments.

Three parallel trial automations
Built 5-email nurture sequences for ATS, Recruiter, and Workforce trials, each tailored to that plan's specific features and value proposition. Each sequence:

• Welcomes the contact and confirms trial end date
• Encourages recipient to book a demo with sales staff
• Surfaces plan-specific feature highlights and testimonials
• Communicates trial extension at the 14-day mark
• Sends a final-day reminder before trial expiration

Automation Structure

Conversion Logic

Built an IF/THEN check before every send: if a contact converted to a paid plan during the trial, a tag value would be sent from the RecMan CRM to Mailchimp. This was coordinated with the client DEV team. IF the contact had one of these conversion tags, they'd be pulled from the automation, re-tagged as a converted customer, and removed from the "do not email" suppression. If they didn't convert, they flow through to the next touchpoint, and at the end of the sequence get tagged as a non-converted lead for separate follow-up.

We recommend using a "Marketing | Do Not Email" tag to exclude contacts who are in onboarding automations from receiving standard marketing messages. This ensures that new contacts are reviving the most relevant messages based on their funnel stage and reduces the chance they may receive more information that complicates their buying decision.

Email Templates
Designed and built the email templates, including merge-tag personalization, CTAs, feature bullet blocks, and testimonial modules that could be swapped per plan tier. We worked with the RecMan staff designer to create whimsical branded images that matched the subject matter of each email.

Content Production
Wrote the email copy and built a content production doc to keep subject lines, preview text, and body copy consistent across all three trial tracks while still differentiating messaging by plan.

The Result

A self-running onboarding email system across three product lines that requires no manual tagging or list management from RecMan's team. Contacts that converted from trials to customers are automatically removed from nurture sequences and routed into the customer list, while non-converted leads are cleanly segmented for retargeting.

This entire system, from contact segmentation through the final trial-expiration email, was built and tested ahead of RecMan's platform launch. Every automation path, tag trigger, and conversion check ran through validation before a single real trial contact entered the flow, so the nurture sequences were live and working from day one rather than being patched together after launch.

Because this build was completed and validated ahead of launch, performance data wasn't yet available at project hand-off.