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Making the most of your funnel: the ‘Hail Mary’ email

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This is a lifecycle email success story.

At Vero we’ve recently switched from Zendesk to Help Scout. There are a number of reasons for this but, honestly, the main reason is that Help Scout gave me the opportunity.

That’s right…Help Scout asked me to sign up and sign up I did!

If you want to learn how to reactivate customers for your online business then this is a golden example.

Let’s start with a little story

I first signed up to Help Scout on behalf of Vero on 17 June 2012. Here’s me logging my first test ticket in Help Scout, within a few minutes of signing up:


At this point, in metrics-speak, I have pretty much activated immediately. It’s looking like I’m going to be a golden customer!

…and yet, due to time, a Knowledge Base we’d already built up in Zendesk and a few other decisions (Zendesk’s customer triggers are cool) we never got into Help Scout.

We became inactive trial users and, alas, Help Scout sent me this 15 days later:


I went on with my life. Help Scout went on with theirs…but then, 12 days later, I got this:


Oh yeah.

Help Scout asked me for feedback and, not only did I fill out their feedback form providing lots of great tips and useful feedback but I sought out Nick Francis’ email address (Help Scout’s founder) and got in touch personally.

Perhaps I’m a little more interested in lifecycle emails than the average punter but this email clearly had an impact.

“You switched at this point, right?”


Even after having spoken with Nick and being thoroughly impressed with the simplicity and consistency of Help Scout’s lifecycle emails, I had my head down working my butt off on other things…so the status quo remained.

This is my inbox from June 2012 to February 2013.

Firstly, the team at Help Scout provide some awesome content. You can see that, almost without missing a beat, I was getting a nice little update, eBook or blog post in my inbox every seven days.


I’ll admit I didn’t read all of these but I read a great deal and they were always killer thanks to Gregory Ciotti’s great insights. Go see their blog for yourself.

The hail mary, AKA the money maker

20 December 2012. Let’s set the scene.

Right now I’m a customer who signed up way back in June (six months ago), I actived my Help Scout mailbox quickly but never sent or managed any HelpDesk tickets. I did provide some feedback and have been back to visit the blog a bunch of times but I havne’t logged in or even tried to.

I sound like I could easily be a customer that is lost for good at this point.

Yet Help Scout sent me this:


I like to call this the ‘Hail Mary’ email. Six months after my last in-product interaction I get a a full 45 day free trial. That’s a massive three times the standard trial. It’s super generous.

So I take them up on their kind offer and 45 days later, I get this in my inbox:


Hook, line and sinker…HelpScout got me!

So, why’d it work?

I was what we might call a ‘high quality’ customer right from the word go.

As the wonderful Lincoln Murphy over at Sixteen Ventures writes:

lincolnCustomers rarely wake up one morning and decide to leave you… in fact, chances are the seeds of their churn were planted before they were even a customer.

– Lincoln Murphy, SaaS optimization expert

Similarly, the seeds of quality customer are planted from the beginning. As I signed up and activated super quickly the writing was on the wall that I was interesting. I had signed up and invested time in getting started. Help Scout could also have tracked my regular email opens, my blog post skimming and other minor interactions to detect that the interest remained.

Track this good stuff. Know where your customers are at any given time. Can you pull up their name and see each action they’ve taken? I hope so!

They also provided an offer that was too good to refuse. The truth is I was never in love with my other solution (I did sign up for Help Scout whilst I was a ZenDesk user, after all) and an offer like this seemed too good to pass up.

Test different offers and ideas to find the sweet spot for customres at different points in your product’s lifecycle.

Around the world in 180 days…

It took me 244 days to choose a plan with Help Scout. That is massive, ridiculous, frustrating, infuriating…it is certainly a long time, if nothing else.

The fact of the matter is that I am now a paying customer. Even better, I’m a quality customer.

SaaS is a tricky game: it takes a long time to get the balling rolling but once it’s rolling it can really snowball. Another 45 days by way of a generous free trial isn’t much of an investment when Help Scout had already waited around 200.

Help Scout were really smart to keep in touch as they did and even smarter to give me such a great offer at that particular moment in time.

lincolnWe generally get around 10-20% of abandoned trials signing up a second time. This email is a big part of that. Personally, I’m always thinking about how we can create a lasting impression and, for that, this sort of email is simply the right thing to do!.

– Nick Francis, CEO Help Scout

I think you can agree that it has certainly paid off now.

Plan for the long term. You’re going to be in business for a while. Plan ahead, it’s worth it.

What YOU should do right now


This is an excellent example of a full lifecycle email marketing campaign from start to finish.

You should use it as inspiration.

To keep things simple: where in your business can you use a similar campaign? If you’re a SaaS company I’d recommend emailing customers that sign up, begin activation and don’t convert with an email like this 60-100 days after their trial ends. Give them something really generous. Something they won’t expect at this point in time.

You’ve spent countless hours and lots of money to get these customers in the door. Don’t miss an opportunity to see a return on your investment.

If you’re an eCommerce store, or have a similar business model, consider the same: track customers that almost purchase, or even do purchase, and haven’t returned in 60-100 days. Email them a special offer. Make it feel personal: perhaps offer previously loyal customers a sneak peak at a new collection or similar.

This email will reduce your churn and increase your revenue. Try it today on customers you know haven’t been back in a while and, when it works, set it up permanently!

Would you have converted with an email like Help Scout’s? What other companies have you seen doing lifecycle emails this well?

PS – If you want a hand getting setup with a campaign like this, just drop me a line at chrish@getvero.com.

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