17 Tactics to Engage New Paid Subscribers, Members, Donors, or Customers

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From the moment a reader chooses to support your work through a paid subscription, membership, donation, or purchase, the clock starts ticking. If you don’t build an engagement habit with them within the first few weeks, they may never return to support your work again.

So those first 100 days after someone pays are crucial. They’re your chance to do a few things:

• Get those supporters into the habit of reading your work or your newsletter.
• Establish trust with them and tell them more about you.
• Get to know them better.
• Drive them to take a next step.
• Integrate them into your community.

It’s a lot to do — but if you do it well, they may support your work for years to come.

Whether you’re a newsroom trying to keep its subscribers, a non-profit asking readers to continue to donate to support your work, or an independent operator trying to get readers to pay for access to your newsletter, products, or community, there are a lot of steps you can take to build habit, establish trust, and drive engagement in those first 100 days.

I recommend automating many of these steps so that a reader automatically receives a series of emails — each with a next step to take — in the days and weeks after payment. But this sort of strategy goes beyond just sending a few emails after they pay. There are other tactics you can try to make sure you keep these readers engaged and get them to support your work in the long term in various ways. Here’s where I’d recommend trying in those first 100 days.

1.) Immediately offer a next step

A reader may never be more engaged than in the moments after they pull out their credit card and pay to support your work. And yet, so many newsletters and organizations miss out on that moment. Sure, they’ll send a follow-up email or two later, but they don’t take advantage of the moment right after that credit card payment goes through.

Instead, drive readers to take the next step as soon as they make their payment. I love how Puck, a newsletter-first publication, does this. Once you’ve paid for a subscription, they immediately funnel you to a confirmation flow where readers can:

• Share more information about themselves.
• Sign up for new newsletters.
• Click through to top-performing stories.

But you don’t have to build a super-sophisticated payment flow like theirs. A good thank you page — featuring a call-to-action, or CTA, to read a story, subscribe to a newsletter or podcast, or answer a few questions might be enough.

2.) Thank them for their support

Whether they pay $1 a month or $500 a year, make sure readers understand that you appreciate their support. Don’t just send them a generic email. Write a letter to them — maybe that comes from you, if you’re an indie newsletter operator or your boss, if you work at a larger org — thanking them and reminding them what they’ll get for their support. (An easy subject line: “Thanks for supporting our work!” That always drives a high open rate.) Make sure it comes from a real person, and add a sign-off from them — and maybe their headshot or a replica of their signature — below that. If you can, add a little nudge at the end, too. Maybe you want them to reply to your newsletter to answer a specific question, or maybe you want to point them toward ways they can engage with your content. (You can also do this in later emails, as I’ll explain later in this piece.)

This is the kind of message you should send in the first 24 hours after someone subscribes. A 2022 report from Piano, a subscription platform, found that, on average, 8.6% of readers cancel their subscription in the first 24 hours. (In some cases, Piano found that as many as 33% of readers cancel in the first 24 hours.) If you wait more than a day to take initial steps like sending a thank you email, you may have already lost a percentage of your supporters.

3.) Make sure they get your flagship newsletter

One of the best ways to keep readers engaged with your work is to send them your flagship newsletter — whatever the main daily, weekly, or monthly email is at your org. But how do you get them on your list? You’ve got a few choices. (By the way, if you’re an indie newsletter operator, and readers paid specifically to get your newsletter, then you can ignore this part — your newsletter is the flagship!)

• You can auto-enroll them in your newsletter — Before you do, check to make sure this tactic is allowed in your region. It’s totally fine in the U.S., but European-based companies tend to be restricted by General Data Protection Regulation, or GDPR. If you do auto-enroll new supporters, make sure you tell them that they’ll do that on the checkout page when they subscribe, become a member, or donate. Also, ensure you’ve got a preference center where readers can easily opt out of unwanted emails, and then remind them in confirmation emails that they can change their preferences if they want. 
• Let them enroll on the checkout page — Instead of automatically adding them, give readers the chance to opt-in via a checkbox on the form where they pay. (Some teams will have this box pre-checked — again, what you can do may depend on where your newsletter or business operates.) But a checkbox is a good way to make sure every reader can opt in or out as they pay.
• Give them the chance to opt-in via a follow-up email — The other option: Send a follow-up email encouraging them to sign up for the newsletter. This won’t drive as many new sign-ups as the other tactics, but it will make sure only readers who absolutely want your newsletter opt-in.

However you do it, getting them onto your newsletter list is a key step to building a regular engagement habit.

4.) Tell them more about you and your mission

Too many newsletters don’t take the extra moment to establish trust with their readers. Yes, these readers have already decided to support your work, but you shouldn’t assume that they know everything about you already. Use this as an invitation to continue to build the relationship.

That starts with a letter from you to your reader. Send this a few days after the initial “Thank You” email. (Some teams like to A/B test the timing of these emails, but I’ve found that the timing doesn’t make a huge difference in performance. Feel free to send this email two to five days after the “Thank You.”) In this letter, tell them about who you are and why you do the work you do. Remind them of your mission and what makes your work different. If you’ve got co-workers, introduce them in this email — include a detail or two they wouldn’t get in the bio on your site.

This email doesn’t need to have a fancy design — in fact, a text-only version of an email might perform even better than one with many design elements! The goal here isn’t to sell something or drive a next step. If a reader walks away feeling like they know you a little bit better, this email has done its job.

5.) Drive a +1

Part of the reason you don’t need to focus on driving a next step in the previous email is that you will save it for a dedicated email — something I call the +1 email. Why the +1? Because you’re trying to get readers to take one more step.

Some teams like to promote multiple things in a +1 email — a podcast, an event series, newsletters, social media, etc. That’s totally fine, but you can also use it to promote just one thing.

This type of email is more important than you think. I’ll give you an example: At the New Yorker, we discovered a curious thing about our podcasts. I was under the impression that all our readers knew about our podcasts, including “The New Yorker Radio Hour.” Our editor-in-chief, David Remnick, hosted the podcast. We promoted it in just about every magazine issue, on our website, in our newsletters (including a newsletter all about our podcasts), and via our radio partners. To me, our podcast promotion was absolutely inescapable!

And yet, when we included a +1 email in our series to new readers, I regularly got emails from readers who said, “This is so exciting about the brand new podcast you launched!” — even though the show launched two years earlier.

The point is: It never hurts to promote and continuously promote your work. Many readers might be hearing about it for the first time. This is the type of email I’d put into your post-payment automation and send in the first one to two weeks after a reader makes that payment.

6.) Learn about them and their interests

The more you know about what a reader cares about, the better you can tailor specific emails to their interests. That’s where progressive profiling comes in.

Progressive profiling is when you slowly collect additional information about a user. Some newsletters will ask for this information immediately after you sign up. They’ll show a little survey where readers can answer a few questions, and that data will be added to your email profile. Other teams might tag a user based on the response to a poll or collect a bit more information when a reader registers for an event. Knowing a little bit more — who a reader is, which topics a reader most cares about, what they do for work, or where they live — might help you down the road. If you’re trying to target a specific part of your audience with a specific CTA, you’ll have the information you need to identify the right readers. (Knowing only an email address or first/last name won’t be enough.) Let’s say you’re launching a new newsletter all about sports — if you know which readers care about sports already, you can target them with an opt-in message and drive lots of sign-ups at once.

I’ve even seen examples where orgs might ask about a reader’s interests and then later send a welcome email to those readers customized from that data. Imagine you’re a local newsroom covering three big topics: City government, schools, and local restaurants. In your welcome series, you might ask readers which of those three topics they care about — and then the next email in the series could come from the editor of the section you selected.

Also, this data could be used to send personalized newsletters to readers featuring content you already know they’ll be interested in. Personalization is a more advanced tactic, but collecting this data early on allows you to set up personalized messages down the road.

7.) Showcase your best work

Just as readers may be unfamiliar with many of your product offerings — like events, podcasts, or newsletters — they also might not know about some of the great content you’ve produced. Don’t just hope they’ll find something from your archives. Deliver it directly to them.

If you’re a local news outlet, that might mean rounding up a few of your best stories from the previous year or two and highlighting them in an email. Don’t pick anything too time-sensitive. The goal is to find evergreen pieces that aren’t pegged to a specific moment in time.

If you cover another topic — cooking, marketing, pickleball, whatever — create a list of the best-performing stories you’ve ever written, and craft an email showcasing these stories.

This email could come from a specific writer or editor on your team, but I’ve also seen cases where three or four writers might each highlight one story they love within a single email. And if you want to send multiple emails like these — for instance, one from your business editor and another from the sports editor a week or two later — that’s fine, too!

Readers have paid to see your best work, so bring it to them right away.

8.) Ask them questions

You can ask questions one of two ways. The first is to do it right there in your emails. I’ve found that the more specific the question, the better. “Hit reply if you’ve got any comments for us!” won’t get you much feedback, but a more interesting question might get lots of replies. Ask something like:

• What’s one local restaurant you’ve tried recently that we should review?
• What’s one big challenge you’re facing at work?
• What’s one book you read recently that you couldn’t put down?

The better the question, the more replies you get. And if you get lots of replies, you might be able to turn those into content ideas. For example, those replies about a local restaurant might lead to a crowdsourced post: “15 Restaurants Our Readers Say They Love.”

As a bonus, those reader replies often lead to an improvement in deliverability.

The other strategy is to send a reader to a form where you collect feedback or ideas from readers. Ask your question — “Who makes the best burger in town?” — and then send readers to a form where they can enter their answer and hit submit. (A bonus of this strategy: For busy teams, there’s a bit less of a commitment to reply to each email, though you lose out on some of the deliverability benefits.)

9.) Invite them to events

Speaking of exclusivity: If you run events, make sure your paying supporters know about them first.

Don’t you hate it when you hear about an event a little too late and find out that it’s already sold out or you can’t get a babysitter in time? It’s especially annoying if you’re paying to support the writer or org behind the event. Shouldn’t you have heard about the event before the rest of the list?

This should be an easy win for you: Make sure the announcement email for any event goes out first to your paying supporters. Give them a pre-sale window to buy their tickets, and make sure to tell them that as paying supporters, they get the first chance to buy. Even if they don’t make a purchase, you’ve still reminded them of the value of their support.

You could also consider running events just for paying supporters — you have to be a subscriber, member, donor, or customer to get access. Some businesses even offer these exclusive events as a premium tier, so readers have to pay a little bit more to get access.

10.) Get them to engage on social media

One of my biggest pet peeves is when a newsletter casually throws this line into an email: “Follow us on Facebook, Instagram, or YouTube!”

There’s nothing wrong with asking readers to follow you on other channels — more touchpoints with a reader give you more chances to drive engagement or revenue. But if you tell them to follow you, you should also give them a reason why.

I’ll give you two examples — first bad, then good:

❌Follow us on LinkedIn.

✅Every weekday, I’m sharing new marketing tips and tricks on LinkedIn. Make sure you follow me there for the latest marketing advice!

The latter gives readers a clear sense of “why.” Lots of people operate both a newsletter and on a social media platform. Don’t just tell them that you’re on a platform — tell them why it’ll be worth following you.

11.) Remind them of the exclusive things they’re receiving

Here’s a hypothetical: Let’s say you’re flying somewhere. You’re on Delta in one of their upgraded seats. A flight attendant will pop by your seat a few minutes into the flight to ask you a question. “Thanks for flying with us in Delta Comfort,” they’ll say. “Can I interest you in a complimentary cocktail or maybe one of our complimentary premium snacks?” It’s a nice touch — maybe you paid for the upgrade just to get the roomier seat, but now you’re reminded of the other perks that come with it. Even after you’ve paid for the product, they make sure you see the full value of your purchase. (After all, you might need to fly somewhere else soon!)

The same is true for your paying supporters or customers. Sure, they paid for a subscription or bought a digital course from you, but what you need to focus on next is that they actually use the product to its fullest. So send them reminders about what they paid for. Maybe that’s a nudge a week after they buy an ebook with reminders of all the good stuff they can still learn when they reopen the book. Maybe it means adding a label on premium stories within your newsletter to show them that they get access to content like this (i.e., “Just for paying subscribers like you”). Maybe it’s a note at the top of an email reminding them of their supporter-only benefits.

Your job isn’t just to get them to pay once. As soon as they’ve purchased that membership, the clock starts ticking until their membership is up for renewal. The more you can add these small nudges about the exclusive access, content, and benefits they’re receiving, the likelier they’ll use these perks and renew their support down the road.

12.) Take them behind the scenes

One of my favorite non-profit tactics is when they send a regular behind-the-scenes update to their donors. This sort of email could go out anywhere from once a month to once a quarter, and it’ll often include a few sections:

• A big update on something they’ve been working on lately.
• News about new hires or initiatives.
• Popular stories, blog posts, or videos published since the last update.

These typically come from someone senior on staff, and they feel like a letter to readers. The design is often fairly minimal; the goal is to make it feel like someone’s taken the time to tell you a bit about what’s going on in their world. (If you’ve ever had a friend who sends you a letter around the holidays — “Life is good here in California! Jenny is starting second grade and loves to read, and Billy is just starting to walk.” — you know the vibe of these letters.)

You never want a reader to approach their next payment and ask, “I wonder what this org has been doing with my money lately?” These sorts of letters are designed to keep them in the know so they can see exactly where you’ve been investing your time and their money.

Here’s a great example of this from the Salt Lake Tribune. Their email comes out on the last Thursday of the month. Their editor-in-chief, Lauren Gustus, sends a note about something they’ve been working on. Maybe it’s the results of a recent survey — they’ll walk through what they learned and what they will do next. Or maybe they’ve been publishing a series of investigative stories, and they’ll use this email to pull back the curtain and talk about why they’ve made certain choices during their reporting. Readers who read it feel like they’re a part of the discussion about the future of the Tribune.

Plus, they do something I love: Every email includes an additional call to action to donate. 

Now, the Tribune has an unusual business model: They’re a non-profit with a subscription strategy, so readers can pay for access to exclusive Tribune content and make tax-deductible donations to the Tribune. Everyone who gets this behind-the-scenes email has already paid to support the Tribune’s work. But what I’ve seen from orgs like theirs is that these emails drive additional donations — readers get that behind-the-scenes peek, like what they see, and decide to give a little bit more.

(And I’ll note: Many non-profits even have a more exclusive update for donors who give above a certain amount. Those “major” donors deserve an even more personal touch.)

However, anyone, not just non-profits, can deploy this tactic. Pick a cadence for this email, and make sure to keep your supporters in the loop about everything you’ve been working on.

13.) Introduce new features or benefits

Any time you launch a new feature or product, tell readers about it. Maybe it’s a feature you know readers will love, like a new crossword puzzle. Maybe you hired a new staff writer to cover a topic you haven’t been able to cover before. Maybe it’s for a feature readers have been begging for, like push alerts on your app or audio versions of articles.

Make sure they always know about what you’re making for them. Yes, you might also tell them about these features or benefits in a regular newsletter, but they might not see it if it’s alongside other content. I think it’s also worth sending a dedicated email about these announcements.

14.) Encourage them to join your community

Community might mean joining a private group — like a Discord or Slack group just for supporters. (Those types of communities can be an incredible resource but also an incredible amount of work. We wrote all about the pluses and minuses of a paid community in this piece.) But it also could mean something smaller, like inviting readers to join the discussion in the comments section or to attend a free webinar where they can ask questions and be part of the conversation. 

Convincing them to renew their support might be a lot easier if they feel like they’re a part of something bigger than your newsletter.

15.) Remind them of the value of their support

You’ve already thanked them right after they made that first payment, and that’s a great step. But I’d encourage you to thank them again.

Pick a day, maybe 60 or 90 days after they chose to support you, and send them another thank you. (You can automate this email so it goes out at exactly the right time.) Unlike your initial thank you, with this email, you can focus less on the benefits they receive and more on why their support matters to you. Make sure this letter feels personal — it should come from someone on your team who can make the case for why each supporter truly matters. Tell them about the work you’ve been able to do thanks to their support. Remind them that you can’t do this work without them.

I know this type of message sounds a little cheesy. But there’s real power in being told, “Thank you! You matter to us!” And that’ll make a difference the next time you ask that reader to subscribe, donate, or buy.

16.) Celebrate your wins with them

When you do something great, tell your supporters about it.

Won a big award? Announce it in a dedicated email.

Hit a big anniversary or milestone? That’s a great time to send a dedicated email.

Achieved a big goal, like reaching your fundraising goal in an end-of-year campaign? You should send an email about that, too.

Tell them the news — and remind them you couldn’t do this great work without them.

17.) Check-in to see how they’re doing

I subscribed to a new site a few weeks ago, and I’ll confess: The site is a bit of a mess. I have to log in over and over again. There are videos on the site that autoplay and are basically impossible to close, which messes with the reading experience. Their website crashes constantly when I try to read it.

I’d tell them this directly — except for the fact that they haven’t asked.

Check-in with these readers a few weeks after they pay to support your work. Ask them how things are going. Ask them what you can do to help them get more from their subscription, membership, donation, or purchase. You can send an email asking them to reply with their feedback or direct them towards a survey. Either route is OK.

You’ll find that many supporters will tell you that it’s great — keep up the good work! But others will help you identify bugs or issues that need to be fixed. By creating that feedback loop, you know what needs improvement instead of just guessing.

Imagine how happy those readers will feel when you write back a few months later with this news: “Readers like you have been telling us for months that they’re struggling to log into our website. Good news: We fixed the bug that caused the issue, and now you shouldn’t have to log in again every day!”

You’re going to get a lot of happy replies to that message, and those readers are absolutely going to renew their support the next time you ask.

What should you do with all these tactics?

I don’t expect you to implement each of these ideas. A large newsroom might implement more than a dozen of these tactics; an indie newsletter might try just three or four. Whatever you do is better than nothing — as long as you do something in the first 100 days after readers pay.

My advice: Automate as much of this as you can. Many teams will build out a series on the first day that might look like this:

• Immediately after a reader supports your work: Thank you email
• Day 2: Tell them about you and your mission
• Day 4: Drive a +1 
• Day 7: Showcase your best work
• Day 15: Learn about them and their interests
• Day 30: Check in to see how they’re doing
• Day 60: Remind them of the value of their support 

But you could adjust the timing or add more to that series if you wanted.

Other teams do less with automation and focus instead on sending regular communications — like the behind-the-scenes letter — that go out to their entire paying audience. That’s also fine.

Don’t just assume that what I’ve outlined above is what will work best for you, too. Test out different ideas and see what drives the best results with your audience. As long as you make a point to get in front of these readers to tell your story, remind them of the value of your work, and thank them for their support, you’ve got a chance to keep these supporters for a long time.

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