Email marketing is not only cool advertising campaigns but also email newsletters that help build loyalty and engage subscribers in communication. How to do this so successfully that you can additionally get the opportunity to monetize your email newsletter? How to work in large teams? What trends in the email newsletter industry will be strong in 2024?
To talk about these topics, we invited Dan Oshinsky, an email marketing consultant and founder of Inbox Collective, who previously worked as Director of newsletters at BuzzFeed and The New Yorker.
Interview Expert
How experience in large-scale projects influences the approach to email marketing
Stripo: You've held key roles in many well-known organizations. How did your experience at BuzzFeed and The New Yorker influence your view on the email marketing landscape?
Dan Oshinsky: BuzzFeed and the New Yorker were both very important experiences for me working at those two organizations.
At BuzzFeed, I learned a lot about:
- how to test new newsletter products to measure success with newsletters;
- how to work with a large growing team;
- how to move quickly to build new newsletters, grow newsletters, and figure out strategies to engage readers.
At the New Yorker, a lot of my work was on figuring out how to work with the New Yorker's amazing team. Strategy on monetization through ads, subscriptions, and events. To understand how we could use email to serve all the different parts of the New Yorker organization.
And now, in my work with Inbox Collective, I've taken so much of what I've learned at those places around growth, working with large teams, and strategies for testing and monetization.
In terms of my clients, I work with everything from one-person newsrooms and individuals to a lot of solopreneurs who have their own businesses and with large multinational corporations as well strategy.
It's a fun mix of things; everyone needs something different to make their email strategy work.
S: With over hundreds of newsletters launched under your guidance, what was the most challenging part of overseeing such large-scale projects?
D: I think the biggest challenge I see for organizations launching lots of newsletters is figuring out how they communicate learnings and data to their team. So many organizations are willing to launch lots of newsletters but then need to find ways to work together to say, what are we doing?
Well, what can we improve if we look at all the data? We have to make the right decisions. Figuring out how to share that knowledge internally can be a real challenge. Something that I take from my experience is to really encourage the clients and teams that I work with to find moments and places where they can share knowledge.
That could be a monthly email update that goes to key stakeholders talking about what worked and what didn't that month. Or it could be something bigger, like a regular meeting.
For example, this year, I worked with a team that launched their own conference. That was just for their key stakeholders internally, a one-day event where they had different people from their organization present around strategies and learnings. What worked well for us this year? What are we testing and trying to improve for next year as a way to share that knowledge? I see that when you have an organization with lots of things going on, you must find ways to share the knowledge.
So everyone can learn from the other people who are part of your team and are doing amazing things. That is the big challenge.
Three tips to build a successful newsletter strategy
S: What are the key features of newsletter strategies for newsrooms, nonprofits, and independent newsletters in growing email audiences, engaging with readers, and monetizing email programs?
D: There is a lot of advice out there now around email and newsletters, but a few key things still matter to every newsletter.
1. Understand who your audience is
There, one is making sure that you have a clear audience in mind and know exactly how you want to serve them. So many newsletter operators told me: “You know the audience for my newsletter is everyone because anyone could be a reader of my newsletter.”
No newsletter reaches everyone. Who are you really trying to reach, and why is your newsletter going to be valuable to them today?
There are lots of newsletters that exist. You have to make a really compelling pitch for why this newsletter is going to be valuable. Why should I make space in my inbox for it?
So, understanding the audience and the value that you bring is super important.
2. Align your strategy around growth and content with how you monetize
I think another key thing is aligning your strategy around growth and content with how you monetize. If you have a subscription offer, you may be thinking about which content you want. What tactics do you want to use to convert readers to paying subscribers? That's going to be different if your strategy is built around monetizing through advertising or selling courses, merchandise, or books.
Making sure that you have that connection between how you monetize and your content strategy.
3. Engage with your readers
The thing is making space to engage with your readers by asking readers questions and encouraging them to talk back directly to you. An amazing feature of email is that someone can hit the reply button and talk directly back to you, the person who wrote the newsletter. You can also think around stuff like polls or surveys to collect feedback from your audience and ensure that you're incorporating that into your strategy and building a newsletter that reflects what your readers want.
I think those are the three big things to do right now. I see that allows a news organization, a nonprofit, or an individual business or writer to succeed with their newsletter strategy.
Mistakes and ways to improve strong email marketing strategies
S: As a consultant, you make email marketing strategy audits for your clients. What are the three most common mistakes you've seen companies make?
D: I see three big things that always come up in these strategies:
- Not set up the deliverability best practices — like SPF, DKIM, or DMARC. Organizations have issues with email clipping their newsletter, which gets cut off, and it causes underreporting or misreporting of their data. That's really important to correct.
- Not give additional reason to sign up. Organizations say: “Our list isn't growing, so why not?” When I look at how they market their newsletter, all the signup box pop-ups or various widgets on their website say the same thing: Sign up for our newsletter. But there's no additional reason. There's no value presented. So then we have to go back and talk around, well, how do we want to present this newsletter in the best possible way? No reader says: I wish I could sign up for more newsletters — if only there were more newsletters out there! You say: well, this is why my newsletter is valuable. Your time is busy. I understand that. This is why this newsletter is right for you and you want to make time for it.
- Not clean email list. So many organizations that I look at do not have a policy to remove email subscribers who are not engaging. They do not run win-back campaigns. If you don't open emails, you don't click on emails. You still stay on the list, and that can hurt deliverability in the long run. So I always encourage those teams to think around. How do you build some sort of reactivation series, and what kind of policy do we want to set up to say if this person does not engage within 90 days, 180 days, or a year? This is what we plan to do with them: try to get them to come back and see if they will be willing to say goodbye and remove them from a list.
S: Your article outlines ten ways to improve an email strategy in the next 12 months. What's an underrated tactic you would recommend? Or you could comment on the one most important of these ten.
D: I'll go back and mention it again: surveys are really valuable for building a strategy. Much of that article was written specifically for nonprofits in the US. However, any organization with an email strategy or any individual writer with an email strategy should make space to talk and listen to their audience.
I find that the organizations that tend to have the best strategies are the ones that have a really clear sense of:
- their audience;
- which content to share with them;
- how often readers want newsletters in their inboxes;
- which monetization opportunities fit with their newsletters.
So it’s crucial that you really listen to readers and understand what they need and what they want more. It is a very underrated and crucial tactic.
S: Please tell us about three dos and don’ts of welcome emails. And why do you think this email series is significant? How many minimum and maximum emails can there be in a series?
D: It's a really good question. Welcome emails are crucial because they drive engagement with readers early on, and the more readers engage early on, the more likely your newsletter is to stay in the inbox and out of the spam folder.
Welcome emails also drive much higher clicks and often a lot of revenue, so they are super valuable. Once you've set up the welcome series, no matter when a reader signs up, you can make sure they are properly greeted and they get to know you, the writer, or the team behind the newsletter.
So there are three things that I like to see:
- Send at least three welcome emails in the first 30 days. You’re allowed to send more — I work with teams that will send up to 15 or even 20 welcome emails over the course of a hundred days after a reader signs up.
- I encourage everyone to have at least one email from the main person behind the newsletter or a senior person on your team introducing themselves and talking about the work they do and why they are passionate about it, so readers can get to know them.
- Add something like a hard-sell email to drive a subscription or sales of a product as part of a welcome series.
Many tools now can even allow you to customize these welcome journeys. Instead of every subscriber receiving the same welcome series, readers might receive a slightly different version of it. It is based on what newsletter they signed up for, whether they've already paid to subscribe or buy a product, or how engaged they are with the welcome series itself. That allows you to create really exciting funnels that can drive readers to take the next step on their journey with you.
Email marketing trends for 2024 and Gen AI applying
S: What email trends do you think will rule in 2024? Tell us more about the most important of them.
D: So, a few things stand out to me.
1. There is a lot of competition in the newsletter space right now, and the people who are going to be winners in the space, I think, will be the ones who are very persistent.
Some people may be doing email marketing because they think it's a bit of a fad or a trend. However, they may not be committed to serving readers via email for the long term if their list doesn't grow as fast as they want. They may move on to the next tactic. They may move on from email to being on TikTok or a social media trend.
Be patient, continue producing good content every week and month, and be willing to play the long game. Because, if you do, you're consistent and stick with it, you should have good results.
2. Partnership opportunities. If you're building a newsletter strategy for next year, think about how you can work with others, whether it's an individual writer or other organizations operating an email. We can serve each other, promote each other's work, and help each other grow a lot of success. I would love to see more newsrooms try that.
3. SMS or messaging apps like WhatsApp have a big future for a lot of this type of communication, and email and SMS are really partners. They go hand in hand.
Smart organizations will start to think about how they can use these tools together for an eCommerce business, which might mean collecting both pieces of data. That way, you can send important marketing updates via email, but notifications around more urgent things like shipping notifications can be sent via SMS.
Individuals and newsrooms that I work with are starting to think about how SMS can be used for direct reader engagement. It can help get readers to reply and talk in a very private manner, and email can be used for big, broad communications. I think these things will start to work more and more together.
S: AI is definitely going to be used more and more in email marketing. When do you think we should apply this? And what are your life hacks?
D: Right now, AI is fantastic for a few things:
- one is it's a great way to brainstorm ideas for subject lines. If I can't quite figure out exactly what words I want to use for a subject line, I'll use AI tools to come up with a few new ideas to help me move forward. It's a partner for me to brainstorm with, I usually take some ideas and edit from there. I don’t just copy and paste from an AI tool but often use it for ideas;
- I also see so many ESPs introducing AI tools to help with things like writing alt text for images. I would absolutely encourage more teams to use AI for those sorts of repetitive tasks. It is really important to write alt text for accessibility, and many teams forget to do it. And if an AI tool can help you make sure that you always have good alt-text, that’s fantastic.
But I think it's significant that any newsletter operator maintains their own sense of a really clear voice. The AI tools are not trained to sound like you. There's always the risk that if you are just using the AI tools to write whole emails, you're not putting your own voice and tone in the email, and they may sound generic.
So right now, I think AI can be a great brainstorming partner. I would expect that AI tools will continue to get smarter and more sophisticated this time next year. We might see that AI tools can do a lot more than they can do today.
Wrapping up
We are grateful to Dan Oshinsky for such a fascinating interview, which we are sure gave you many insights.
Our main insights are as follows:
- always explain the value of your newsletter and why it is worth allocating space in the inbox — this will bring you new subscribers;
- use all methods for subscriber engagement and communication — email marketing tools provide many opportunities for this;
- build your email strategies around great content and think about monetization;
- strong email marketing strategy always starts with researching and understanding your target audience.
Do you have any thoughts on the issues raised in the interview? Write in the comments, let's discuss.
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