11 Things Smart Newsletters Do to Convert Readers to Supporters and Customers

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As you build out your email strategy, you’ll start thinking about ways to better monetize your newsletter, like selling ads, including affiliate links for products you recommend, or experimenting with tools such as Beehiiv’s Boosts feature to get paid to promote other newsletters.

Now, you’re ready to go further — by asking readers to support your work directly. Maybe you’re a creator building out a series of courses to teach readers new skills and want to sell these to your newsletter audience.

Or maybe you’re a newsroom or non-profit that’s already established a reader revenue model and now aim to supercharge your growth.

How can you monetize your newsletter directly? Most newsletters try to drive their readers to become either supporters or customers:

Supporter business models

• Sell a subscription — This is typically where a reader pays, on a monthly or annual basis, for access to exclusive content. 
• Offer a membership — Members pay for access to content, conversation, community, or a combination of the three.
• Ask readers to donate — Readers give an amount of their choosing to support you and your work.

Customer business models

• Sell products — Readers pay for access to a product, like a book or digital course.
• Sell merch — You’re marketing T-shirts, artwork, or another physical product to readers.
• Sell services — Readers want to learn from you or work with you and pay for consulting, training, or other services.
• Sell tickets — You’re selling tickets to an event or conference from your newsletter.

The good news is that whatever your strategy, you’re on the right platform already. Email is an unusually powerful tool for converting readers into supporters and customers. At the New Yorker, internal research revealed that the no. 1 way they turned readers into paying subscribers was through their newsletter — and nearly every newsroom, non-profit, and indie newsletter I’ve worked with has seen identical results. 

There isn’t just one way to convert readers into supporters and customers. Best-in-class newsletters deploy many different tactics to drive revenue. So, let’s discuss 11 tactics I see smart newsletters use. From this list, I hope you can identify a few new tactics to try with your newsletter.

1.) Start small

When it comes to driving revenue, the little things matter — and it takes a lot of little things working together to make a difference. So start small. A newsroom like WBUR in Boston monetizes through donations from readers, and they have two brief asks in every newsletter: A donate button with a heart at the very top of every email, and then a donate button in the footer.

These calls-to-action (CTAs) aren’t very aggressive, but over the course of a year, they drive a steady flow of new donations.

Don’t stop with the header and footer. You could embed small asks within the body of a newsletter, like The Know does.

House ads work, too. These are popular with newsrooms and publishers — in a text-heavy email, an eye-catching ad like this one from The Information might really stand out to readers:

These CTAs can be subtler if that works better for you. When Capital Daily, a local publisher in Canada, gets a new paying member, they say “thank you” in their intro note and then link out to their membership page. It’s a small thing, but it offers social proof that others choose to join in and support their work.

Here’s an example from David C. Baker, who runs a consulting business. His newsletter is rarely self-promotional, but he does include this ask in every footer as a way to nudge readers toward his services.

2.) Put an ask in the welcome series

I’ve written before about the importance of a welcome series — they’re crucial for building trust with readers and are a key tool to help with email deliverability. But they’re also a valuable way to convert readers into supporters and customers. Klaviyo data from Q3 of last year showed that 2.4% of readers who opened a welcome email became paying customers — compared to a 0.08% rate for regular email campaigns.

At the beginning of the welcome series, start small. Add a line or two to that initial welcome email about how readers can support your work, but don’t push too hard. Readers are just getting to know you.

As the series progresses, you can get a bit more aggressive with the CTAs. Here’s a note that Unpretentious Palate, which covers restaurants in Charlotte, North Carolina, sends a few days after sign-up. The majority of the email is a note from Kristen Wile, their founder, but they do include a CTA to become a member towards the bottom.

Later on in the series, you can send an entire email to drive readers. These emails, known as a Hard Sell, attempt to get readers to click, pull out their credit cards, and take the next step. If you sell a product, you might include a discounted offer in the email. If you’re driving readers to donate, you might focus on the value of your work, as The Hechinger Report does in this email.

If you sell something — whether it’s a coffee mug or a paid subscription — I recommend including at least one Hard Sell email in your welcome series. You might even send multiple emails over the course of a few weeks to drive readers to take that next step.

3.) Target specific audiences

Imagine for a second that you work at the Philadelphia Inquirer, and you’re about to send out this subscription offer timed to the NFL Draft. With the actual season still months away, only the most loyal fans are plugged into the entire draft process.

The question is, do you send this offer to your entire email marketing list? Or would you rather target it to non-paying subscribers in your daily sports newsletter — ideally, readers who regularly click on Eagles content?

The latter is almost certainly going to have a much higher conversion rate.

Now, you might be thinking: Is there harm in sending to the full list? What if there are Eagles fans who don’t read the sports newsletter?

That’s certainly valid — you might be leaving some of those readers out! But here’s the flip side: You might also be annoying a reader who doesn’t care about the Eagles, and by sending them this message, you’ve missed out on the chance to send them a targeted email that would be more likely to convert them.

(A brief note: I’ve yet to meet a Philadelphian who didn’t care, almost obsessively, about the Eagles. But for the sake of a discussion around conversion tactics, let’s assume that someone somewhere in Philly cares exclusively about local politics and not the Eagles.)

The other place you might want to utilize this kind of targeting is in your welcome series and regular emails. Your email service provider (ESP) may allow you to show or hide certain content based on whether a reader is an active member or customer. You can show some sections of a newsletter, like an ad promoting a special offer, only to readers who have not yet chosen to pay. (There’s no need to tell your paying customers to pay since they already have!)

4.) Include personal stories

Here’s something I often do with my clients, particularly large newsrooms: I copy and paste the text from one of their recent subscription or membership offers into a Google Doc. Then, I copy and paste the text from a competitor’s offer into the same Doc and remove all mentions of each brand’s name.

Then I ask that client: Can you tell me which email is yours and which is your competitor’s?

You’d be shocked at how often these teams can’t tell which one is theirs.

Most of the Hard Sell emails I see are, truthfully, pretty generic. But readers don’t want to pay for something generic — they want a product that will make a difference in their lives or bring additional value to their work. 

Start by writing emails in a clear, personal voice. I think one of the best examples of this is The Baffler, a left-leaning magazine covering U.S. politics and culture. Their voice is wry and often off-beat, and they lean into that with everything they do, including their subscription offers.

Take a look at one of their messages below. Very few publishers can get away with a subscription offer as ironic as: “Breaking news, fair consumer: simply by being on The Baffler’s mailing list, you (and everyone else on the mailing list) have unlocked an exclusive (to everyone on the mailing list) discounted subscription to our magazine.”

Here’s another good example from Ben Collins, who writes a newsletter about Google Sheets. In Ben’s weekly emails, he takes complex subjects and peels away the layers, bringing his readers tutorials that anyone can use. So it makes sense that the offers for his courses, like the one below, lean into that established format:

• Here’s something about Google Sheets that’s not easy to understand.
• Here’s how I learned it and started to utilize it in my work.
• Buy my new course, and I’ll help you understand it, too.

Whatever your voice, here’s one more copywriting tip: Try to utilize the words “you” and “I” throughout your emails. You’re not broadcasting to a giant audience — write to one reader.

5.) Send one-off campaigns

Throughout the year, you should send one-off emails to try to convert readers to supporters or customers. 

Here are a few ideas for these emails:

• Send an email tied to an important date, like a public holiday or an anniversary, for your newsletter (so long as it makes sense with your newsletter’s content and readership; no need to send a Labor Day email if your newsletter delivers tips on digital detoxing). These emails are often a great opportunity to promote a special sale.
• Send an email when you’re recognized for your work — for instance, after you win an award. Thank readers and ask them to support you so you can keep producing strong content they’ll love.
• Send an email highlighting great content you’ve published recently, and use that as a way to explain what readers get when they support your work.
• Send an email with a personal letter. Tell them a story, then add your CTA.
• Send an email with a limited-time offer. This might be a good opportunity to experiment with a countdown clock so readers can see how long they have before the offer expires.

Here’s a lovely example from Mission Local. Their managing editor, Joe Eskenazi, sent this email out to readers in 2023. At first, it doesn’t really look like a fundraising email. It begins with a personal anecdote about parenting — when you’re a busy parent with multiple kids, you don’t run into the room to check on your kids until you hear “a thud, a crash, and a scream” — but then he ties that back to a larger story about his newsroom, which covers local news in San Francisco.

One-offs like this can be very effective. Make them part of your regular sending strategy. You don’t want to overdo it — if you sent this type of email several times a week, readers would probably tire of them and unsubscribe — but try sending something like this once or twice a month to start.

One more suggestion: You may want to avoid sending these to new readers since they’ll get a few offers through your welcome series. Once they’ve received the full welcome series, you can make the readers eligible to receive one-off marketing messages.

6.) Try larger campaigns

Non-profits have always relied heavily on fundraising campaigns. This may look like a big end-of-year campaign involving a dozen or more emails sent over a few weeks. Non-profits often secure matching funds to encourage donations — for every dollar individual readers donate, the donation might be matched by a generous donor, like in this example from The Leakey Foundation.

These sorts of campaigns usually follow a template: 

• A kickoff email announcing the campaign and the goal.
• Letters from key staff members telling their stories.
• Updates as the campaign progresses, including reminders as the campaign comes close to its end.
• A thank you message when the campaign is over.

These campaigns can run for weeks, and they can raise tens or hundreds of thousands of dollars. But they can also be flash campaigns lasting a few days with a smaller fundraising goal.

There’s a misconception that only non-profits can take advantage of these campaigns. Any newsletter can run these — as long as you first think about the larger story you want to tell.

Maybe your newsletter is celebrating a big anniversary, and you want to convert readers to paying supporters by sending a multi-email campaign that tells the story about the work you’ve done in the past year, with each email including a CTA.

Maybe your campaign is tied to a specific milestone. Let’s say you’re just 50 paying subscribers away from having 1,000 paid subscribers on your list. That might be a good opportunity to send a handful of emails about hitting that big goal.

Or maybe you’re an independent operator who’s just launched a brand-new paid product, like Ellen Donnelly at The Ask. That’s a great opportunity to put together a campaign to drive sales. Announce the product in one email, use the next to answer key questions from readers, and the third to create urgency to buy. (You, of course, are free to send as many emails in a campaign as you like.)

(A bit of transparency: A number of the teams cited in this story, including The Leakey Foundation and The Ask, are Inbox Collective clients.)

7.) Get the most out of your ESP’s features

Your email platform may offer a few tools to help you sell stuff. Every platform is a little different, so check out their feature set to figure out which you can utilize.

Take Beehiiv, for instance. (Yes, they’re this quarter’s sponsor, which is why I’m listing them first!) If you set up a subscription or membership using Beehiiv, they take 0% of any payments — compared to up to 10% for other platforms. Since everything’s inside one system, you can target non-paying readers with specific messages, A/B test different messages, trigger automations based on subscription status, or even paywall certain stories from within a newsletter.

AWeber lets you sell products like books or ask for donations from readers. With ConvertKit, you can set up complex automations to target specific types of readers, like those on a free list, with messages about why they should pay. Substack lets readers pledge a subscription before you’ve turned on subscriptions — those readers only get charged when you eventually turn on the paid subscription function. Ghost allows you to customize your payments page. A newsletter using both Mailchimp and WooCommerce can see, within Mailchimp’s dashboards, exactly how much revenue a specific email drove.

Most ESPs also offer integrations with third-party tools that let you sell stuff, like Memberful or Podia. (These might be direct integrations, or you can use Zapier to connect things.) Take advantage of those integrations so you can clearly track who’s converting — and who you’ll want to target with messages to convert.

One more thing: Take advantage of the metrics your ESP provides. Readers who regularly open and click are far more likely to support your work or buy something than readers who don’t, and you can use those engagement metrics to identify which readers you want to target with a specific email or campaign.

8.) Get strategic about pricing

One mistake I see, particularly in the subscription business, is when newsletters set the price of their subscription based on the price they see others charging. It’s why so many paid newsletters charge $5 a month or $50 a year for their subscription — it’s a fairly common price point.

But it may not be the right price for your newsletter.

Before you set a price for a subscription, I’d encourage you to consider some key factors:

How big is your potential audience? Do you write for a massive audience or a niche one? How easy is it to find the content you create? Be brutally honest with yourself: Are there lots of other writers or creators in this space, or will readers find this content exclusively in your newsletter?

Hard-to-find content for a niche audience, like a business-focused newsletter, might be worth hundreds or even thousands of dollars per year. Content that’s easy to find elsewhere and that’s intended for a massive audience might be worth less than $100 per year. Think about where your newsletter falls on the spectrum below, and use that as a starting place to price your offering.

Smart newsletters often start with a slightly higher price point and then offer occasional discounts, or they’ll use free trials where a reader enters their credit card upfront but is not charged until the end of a specific window, which could be as short as a week or as long as a month. 

Don’t make the mistake of always presenting readers with the same offer. The smartest operators look at the lifetime value of a subscriber or member and then calculate that metric over the course of three to five years. I worked with one team that ran a test to try to learn whether they would generate more revenue over three years if they offered readers a discount of 20%, 30%, or 50% on the first year of the subscription. (The rate increased to the full price of the subscription after that first year.) They found, unsurprisingly, that the 50% discount converted great, but many of those readers failed to renew for a second year. It was the middle offer — 30% off — that generated the most revenue in the long run since readers were far more likely at that price point to renew their subscription for a second or third year.

More resources if you want to go deeper on pricing: 

• I created a guide to pricing strategies you can find here.
• The Membership Puzzle Project put together this resource about how to price a membership.
• Reid DeRamus has written extensively about pricing and retention in his newsletter.

9.) Run A/B tests

As I covered in our big guide to A/B testing, there’s a lot you can test when it comes to driving revenue. You can test out:

• The offer in the email
• The message of the email
• Who the email comes from
• The CTAs within the email
• Whether the email should be text-only or include design elements

Any email that has the chance to drive revenue is one that’s worth testing since even a small increase in conversion rate may drive significant revenue in the long run.

Here’s the advice I give clients, particularly anyone sending to 50,000 or more readers on a regular basis:

You never know which email will convert well and which will be a dud. So, instead of blindly sending an email to your entire audience, run an A/B test on a small percentage of your list. Test out some of the ideas below — the copy, the offer, the personality the email comes from — and see if one version performs better than the other. And compare the results to your historical benchmarks for similar sorts of emails. If the email underperforms those benchmarks, go back to the drawing board and run another test until you find an email that really works.

You only get so many chances in a given month to convert a reader. Don’t waste one of those chances with a mediocre email. Instead, commit to running a few tests to see what works before you send it to your larger list.

10.) Focus on your CTA

The CTA is the final piece of your larger message — it’s the thing that convinces a reader they should click through to your email to support your work or buy something. (It’s often displayed in a button in an email.) You can write a great email, but if the CTA doesn’t motivate the reader to take the next step, your email doesn’t do its job.

Look to the nonprofit world for inspiration with CTAs. As Ephraim Gopin wrote in his guide to email marketing for non-profits, many orgs have moved away from dull CTAs, like “click here” or “read more”:

Instead, think about different ways to drive readers to that next step:

• Save a turtle
• Plant a tree
• Help save nature, Dan
• Be the change
• Contact your congressperson here

I’ll add a few more ideas to the mix based on work I’ve done:

• Try the “Yes, and” approach — The reader’s just finished reading an email that they agree with — they’re already nodding their head “yes.” Now give them the CTA to have them take the next step: “Yes, I’ll support your work!” or “Yes, I believe in this mission!”
• Identify the value that readers care about most — There are a lot of things readers might value about your newsletter — this list can help you identify a few ideas — so mention those right in the CTA. For instance, if you’re selling a course or ebook designed to help readers overcome an obstacle, mention that here: “Let’s take the next step together!” or “Get the solutions you need!”
• Tie it back to a specific number — Let’s say you’re giving readers a special half-off discount. A great CTA might mention that: “Get 50% off now!” Or if you’re a non-profit offering matching funds, mention that in the CTA: “Triple your impact today!”
• Utilize two CTAs together — If there are multiple purchase options, try stacking two buttons on top of each other. An org driving donations might have one button with a link to donate monthly and another for one-time donations. A newsletter selling tickets to an event might have a button for general admission tickets and a VIP offer.
• Add an emoji or icon to the CTA — Don’t overdo it (too many 🚨🚨🚨 emojis might annoy readers), but an emoji that adds a bit more context could drive more clicks. You could also try adding something small, like an arrow emoji (→), as a reminder that there’s a next step.
• Adjust the design of the CTA — Test out different colors or button sizes to see if any make a difference. Or see what happens if you embed the CTA within a paragraph instead of using a button. (Just beware of magic fixes — purple buttons don’t always lead to higher conversion rates!)

11.) Don’t make the same ask over and over

If readers see the same message in every email, they’ll tire of it. A new message may convert well at first, but as readers see it more frequently, they’ll start to tune it out. It’s so important to keep trying new asks within your email.

I love how Crikey, an Australian newsroom supported by paying members, always rotates through different CTAs in their newsletter. One week, they’ll have a straightforward discount on their membership.

The next week, they’ll lean into a message about how each reader can make a difference by becoming a member, with no price point or offer listed.

The next week, they might rotate in a limited-time offer, like this 50% off sale for Boxing Day.

And the next week, readers might get an unexpected message that makes them stop and read: “Don’t agree with everything we publish? Good.”

Maybe a reader will convert the first time they see one of these CTAs. More likely, they’ll need to see a few messages over the course of a few days or weeks before they decide to pay. But by rotating through different messages, Crikey can give that reader several reasons to become a member — they’re not relying on one pitch or one offer to convert.

Plus, they’re incorporating many of the tactics listed in this guide, like sending one-off emails, using house ads in their newsletter, and adding an ask to their welcome series. Smart teams don’t get stuck with one approach or let a CTA get stale. The best organizations and newsletter operators always mix in new approaches. Over time, those teams and writers will be able to identify which tactics work and which don’t, and then lean into the most effective strategies to maximize revenue.

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