How the Toronto Star Uses Promotional Emails to Grow Their Lists Fast

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Working for a publication that’s as established as the Toronto Star has some advantages you’d expect — and some you wouldn’t. 

When I started running their newsletter program in 2018, I knew I had scale on my side like I never had at the startups and upstarts I’d come from. History, too: The Star was founded in 1892, and it’s not even the oldest in the fleet of regional newspapers owned by its publisher, Torstar. (That’d be the Perth Courier, established in 1834.) I took for granted that our audience would be big and loyal, and that I’d have a head start introducing anything new.

What I didn’t realize is what else all that got me: email addresses. Thousands upon thousands of them — longtime print subscribers, site visitors who’d created accounts to read articles before we added a paywall and digital subscribers who’d opened their wallets thereafter. Canada’s strict anti-spam protections, also known as CASL, ensured that all those email addresses belonged only to readers who wanted to hear from us, too.

When I joined the Star, newsletters had been around for about two decades, and we had tried a few ways to sign readers up for them, like ads in the print paper of smiley stock-photo people relaxing on couches with iPads. If they ever worked, they didn’t anymore, and I did not like them. 

What we needed were new ways to grow our newsletter audience. The cheapest and easiest tactic turned out to be one in front of us all along: drawing on the relationships we already had with readers in our email database.

Using email to grow email

While my colleagues in marketing were regularly emailing those addresses with things like article recommendations and subscription offers, it didn’t immediately occur to me to use them for anything else. But when we pulled out all the stops to launch a new pop-up election newsletter in 2019 we called The Lead, one of the things we thought to try was a dedicated promotional email to some of the readers in our database. They’d click a button to be taken to the newsletter page, where they’d select The Lead, enter their email address, and be signed up.

This was that first email:

It broke everything immediately. So many readers visited the sign-up page at once, so many more than had ever visited it at once, that our platform’s API overloaded and crashed, taking our ability to do anything else down with it.

It was a huge pain in the ass, and a very good sign that we’d figured something out. It made an awful lot of sense, too, that people who liked getting one kind of email from us were especially open to another.

What we’ve learned about what works best

We’ve kept going ever since with every new newsletter launch, every big newsletter change, and any other excuse we could think of that would get people excited. I’ll admit that we haven’t A/B tested much, nor segmented, though we probably should have. Still, we’ve learned a lot about what works to get the most out of these promotional email messages. Here’s what’s been most important:

1.) Make it really easy to sign up

The fewer steps between someone going “Hey, this sounds good!” and signing up, the better. Even the best promo email loses people after they click a button to head to a sign-up page, or after they find and select the newsletter on that page, or even after they’ve done all that and started filling in their email address.

We’ve got it down to just one step. When we launched new email alerts for the Beijing Winter Olympics in 2022, two of our developers, Terrence Wong and Jiehao Zhu, figured out how to record someone’s sign-up as soon as they clicked a button in a message. Our email marketing lead, Jason Rudniski, figured out ways to prevent our API overheating again, and one of our lawyers, Cathy Nicholson, helped us nail the language for a super-clear CTA button: rather than “SIGN UP FOR MEDAL ALERTS,” it now read, “START GETTING MEDAL ALERTS.” (We don’t send confirmation emails requiring a final click to officially opt in at the end, either, but recipients can unsubscribe from the welcome email they get.)

Here’s how that final email looked:

Because our old emails lost about half of our clickers before they signed up — many readers clicked to the sign-up page but never entered their email and subscribed — switching to a one-click sign-up doubled the effectiveness of each message. Before, a good email would get 3,000 to 4,000 people onto a newsletter offering; now, with a larger pool of email addresses and a superior conversion rate, a good one gets us 10,000 sign-ups. All of them come far cheaper than paid marketing and faster than any on-site drivers. 

2.) Pin down the purpose

It’s easy to think about how a product like an email newsletter serves you or your bosses. What’s way harder is figuring out what it’ll do for the people considering signing up. At the Star, the better we’ve been at defining a newsletter’s purpose for a would-be recipient, the greater our success.

Here’s the promo email we sent about a pop-up holiday newsletter, for which members of our newsroom baked their way through our cookie-recipe archive:

You can see the purpose to would-be recipients right under the surface: This is here to help you find something to bake for Christmas. Sherina Harris, who always writes these emails for us and coordinates deployments with Yang Chen on our email team, really aced the copy. 

3.) Target the right audience

We know our readers well enough to make educated guesses about what will interest them. Those rah-rah alerts for Canadians medalling at the Olympics, a brilliant idea from the Star’s digital editor Christine Loureiro, were a guaranteed hit for us, but wouldn’t have been elsewhere.

Here’s one version of an email promoting the Star’s flagship morning newsletter, First Up, that performed unexpectedly poorly:

It’s a good email. I know that because the month before we sent it, we sent a successful copy to a different segment of our audience. 

This message, though, went to people we knew far less well — readers who’d signed up for promotional emails from Wonderlist and Save.ca, a contests and deals site respectively, both owned by the Star’s parent company. 

When we sent this message to those 750,079 people, just 979 signed up. Quite bad, and pound for pound, 23 times worse than what we’d just sent to Star subscribers. Even a great email won’t be a successful one without the right audience.

4.) Make it urgent 

Timely emails for timely offerings do best, and timeliness can be about what’s going on in the wider world (a thing that just happened) or simply in someone’s head (a thing they’re thinking about now). We’ve found reasons to send people emails about offerings that aren’t new anymore but are new to them, or simply newly urgent. 

Here’s an example of an email promoting an alert we set up to let readers follow our coverage of an awful unsolved murder — one we knew they’d be especially interested in at the time because of a hit podcast we’d just launched:

5.) Frame the pitch carefully 

Readers don’t see much before they open — just a subject line and preheader text — and there’s no guarantee they’ll read much if they do open, so we fuss over every word outside an email and in it to make them count.

Here’s one example for Food Crawl, the weekly newsletter by the Star’s food reporter Karon Liu. This one had the subject line “Where should you eat next?”, and preview text that read “Find out with the Star’s free food newsletter”:

This is where everything comes together. Is it ridiculously easy to sign up? Did we nail a purpose? Will the audience care? Do they need what we’re pitching them? And do they need it now? 

If the answer to any of those questions is “no,” we could have a bigger problem with what we’re offering than insufficiently snappy copy. But if it’s “yes” to all of them, we know our success in their inboxes won’t end when they click that big blue button.

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