Mailchimp success story · Online estate planning company

How an online estate planning company converted 18x better with automated Mailchimp emails.

Willful helps Canadians write a legally binding will from home. Many customers paused halfway through. Stage-based automated emails, timed to the exact step where each person stopped, brought them back to finish.

Business
Willful
Market
Toronto, Canada
Goal
More customers finishing their will
Couple at a kitchen table reviewing documents together over breakfast

The results.

Automated emails compared with the company’s bulk sends.

  • 18xconversion rate of automated emails
  • 1.7xopen rate of automated emails
  • 40%of Mailchimp-driven revenue from automations

Customers who had dropped off now often come back to finish within days of a follow-up. Figures as reported in the story; Mailchimp does not publish how they were measured.

The challenge.

Willful’s product is simple, but the decisions are not. Customers often paused at key moments, such as naming an executor, to talk with family or think things over, and many never came back.

Reaching each person with the right message at the right moment by hand was not possible at scale. Mass emails could not speak to where someone had stopped, so the gap between intending to write a will and finishing one stayed open.

  1. Track progressEach customer’s step on the website flows into Mailchimp.
  2. Spot the pauseSegments show who stopped, and where.
  3. Send the right helpAn educational email about that exact step.
  4. Test and repeatMultivariate tests improve timing and tone.

What they did.

Marketing automation flows · Segmentation · API integration

Website data in Mailchimp
Mailchimp’s open API brought each customer’s progress from Willful’s website into Mailchimp, so the email system knew exactly where each person had paused.
One flow per stage
Segmented, stage-based automation flows sent educational emails about the step each customer was stuck on, from naming an executor to final signatures.
Hundreds of segments
Willful runs hundreds of segments through dozens of automation flows.
Constant testing
Multivariate tests across the flows showed which timing and tone brought people back, and each journey informed the next version.

Why it worked.

Our read on the decisions behind the numbers, and what any business can take from them.

Timing beats volume
An email that arrives when someone is stuck on a decision is help, not marketing. The same email sent to everyone is noise.
Education builds trust
For a serious purchase, explaining the next step does more than a discount. Customers came back because the emails made the decision easier.
Data makes it personal
Connecting the website to the email platform is what made stage-based messages possible. Without it, every customer looks the same.
Automations keep earning
Once built, the flows run for every new customer. That is why 40% of Willful’s Mailchimp-driven revenue now comes from automated campaigns.

How we would run this play for your business.

You do not need a national budget to use the same ideas. This is how Overtop Media Digital Marketing puts them to work in our mailchimp email marketing.

Map where people stall
Quote requests, applications, bookings and carts all have drop-off points. We find yours in your analytics first.
Connect your systems
Your website, booking tool or CRM sends progress to Mailchimp, so each email matches what the customer has done.
Write help, not hype
Short, useful emails that answer the question behind each pause, tested for timing and tone.
Measure finished sales
We report completed purchases and applications, not opens, with accurate tracking across email and your site.

Who this play fits.

You do not have to be an online estate planning company to use the same approach. It is a strong fit for:

  • Legal and financial services
  • Insurance agencies
  • Online applications and sign-ups
  • Software and subscription businesses
  • Education and course providers
  • Any business with a multi-step sale

Want results like these?

Tell us about your business and your goals. We will show you where Mailchimp can bring you customers, and what it would take.

See how we run Mailchimp for our clients

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Results as published by Intuit Mailchimp in its Willful customer story (January 2026). Results for other businesses will differ. Analysis by Victor Bubuioc, MBA, Digital Performance and Growth Expert, published October 10, 2026.