Building relationships and welcome emails with The New Yorker

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📋 TL;DR key takeaways from this episode:

1. Be mindful of your first message to subscribers. A positive, Hallmark sort of welcome email helps you build a relationship with your audience.

2. Sending a welcome message can help build a habit from day 1, especially with a news outlet. It gets people excited to receive your emails, and introduces what type of emails they can expect.

3. Educate subscribers on how to get the most out of your emails. What's the format? How often are you going to send those emails? What do those emails look like? Help people understand what the value is.

BONUS: Think about the messages in the series of emails you’re sending. How can you get subscribers to do one more thing after they subscribe?

Matt Helbig: What's up, email geeks. Welcome back to another Feedback Friday this week with a very special guest that doesn't run a newsletter at all. 

Dan Oshinsky: No, that's not true. I technically kind of run a newsletter . I'm Dan Oshinsky. I run Inbox Collective. A little consulting firm that works with news organizations, nonprofits, and brands, and helping them grow their email presence.

But I also run Not a Newsletter, which is quite literally a Google doc where I write a couple thousand words every month around what's happening in the email space and how to get the most out of email, but there is an email alert tied to it. Also, the other thing, even though it's called Not a Newsletter and I send it out as a Google doc. I still get daily emails from people telling me how much they love my newsletter. So no matter how much I try to distance myself from newsletters, I can't go too far. 

Matt Helbig: I do have a secret suspicion that it actually might be a newsletter. 

Dan Oshinsky: I am tied to this forever. No matter what I call it, no matter where I go, if I produce this as a Shakespeare in the park. People still tell me how much they loved my newsletter. 

Matt Helbig: Well, you do a fantastic job. So it's well appreciated. Tell me a little bit about your background though. Like what makes you an expert to not have a newsletter? 

Dan Oshinsky: Oh, good question. So I started and built the email team at Buzzfeed, and then later went on and was the director of newsletters at the New Yorker.

So have worked in some pretty interesting editorial spaces launching all sorts of products and now through inbox collective work with two dozen different news organizations, nonprofits and brands, on their email strategy, how they're going to grow their lists, get more readers. Build the right products for emails, and then turn those readers into customers, fans subscribers, donors, members, whatever it is they're trying to do.

Matt Helbig: Well, you had a list of some different emails, around a welcome series. So I think we could walk through a few of those. Now that you say that you've been on the New Yorker, is this one of the emails that you've made before? 

Dan Oshinsky: This was one that we worked on when I got to The New Yorker. The New Yorker was a fascinating brand because obviously established incredible, incredible history. And they had a lot of success with email but hadn't had any sort of email strategy. They had just launched a couple of different newsletters. I worked with our amazing consumer revenue team there and that's the team that helps you actually buy subscription to The New Yorker and we built out a series of onboarding emails. 

The first is, this is what I call the hallmark email. Cause usually the subject line is something that feels like you'd get in the hallmark section of the greeting card aisle. Thanks. Congrats. Welcome. Hello. Some sort of really positive message, and this is the email that goes out right after you subscribe.

You just signed up, and we're going to tell you what you can get in your inbox and then maybe give you a couple of different ways to go a little bit deeper with a brand like The New Yorker. So if you're just getting started, you learn a little bit, you know what you can expect from us, and then we want to give you some other ways to engage more deeply.

Matt Helbig: I really liked this one. It definitely stood out to me as a welcome email. The use of live text . Really using those couple of primary colors of the brand throughout the send. Yeah, definitely a successful email. 

Dan Oshinsky: This is one too, where with live text, with very clear buttons, we didn't go over the top.

We just wanted to keep the asks pretty clear and make sure that, especially if you're on your phone, this is an email that looks good and renders really nicely. We also really want it to tie in some of the art that The New Yorker is known for too, which is fun and give it a playful kind of different feel.

Matt Helbig: It looks fantastic. So why are welcome emails so important to you? Why do you think they're a good. first impression for a lot of brands?

Dan Oshinsky: One is it makes a first impression. I want to come out really strong in those first couple of emails, the first 30 60 days and make sure that I introduced you to who I am, what I'm all about, the people on my team, and start to build a relationship.

And for me, especially if you're a news organization, you're a nonprofit, you're a brand, you're sending regular emails. If I sign up for your email, especially if you're a news organization. I sign up for your daily newsletter. Well, I don't really know what that means. Am I getting headlines? Am I getting something curated in my inbox?

When is it going to show up? Who is going to be writing it? Just trying to set, you know, using these types of emails, the hallmark email to set the tone for the relationship going forward, and also try to build the habit from day one. So if I know that maybe I'm going to get, you know, an email, when does it show up in the inbox?

Who's going to be writing it? Trying to build these in from the start so people can build a habit with us and get excited to get their first email in the inbox. 

Matt Helbig:  I think for some publications that we've looked at before, this sort of a welcome email is sort of missing. 

Dan Oshinsky:  It's something that all brands should be doing. There was some research the Iterable team did last year where they found that in the news space 70%. of brands where not sending any welcome email, and just anecdotally, that really echoes what I've seen in the work that I've done. So many news organizations, including ones that are pretty big and pretty powerful. You'd be surprised at some of the ones out there that send absolutely no welcome message.

You sign up for a newsletter and then suddenly something just starts appearing in your inbox. You don't really know what it is or how to get the most out of it. So this is just a huge, huge opportunity for, certainly for news organizations, but I think any sort of brand that's doing something with email. Set the tone early on, start building a little bit relationship, make sure people know how they're going to get the most out of what you're going to be sending them.

Matt Helbig: This one is from Vancouver is Awesome. 

Dan Oshinsky: Yeah. So these are from some guys that I've worked with through Inbox Collective. They have a really amazing and daily newsletter. And so we did a couple of things with this. One is they're a really small team, but they have just amazing personalities. We really wanted to have a positive, fun, upbeat kind of tone, as you would expect for a site called Vancouver is Awesome.

They are not shy about being enthusiastic about how incredible their city is. And so that first sentence, "Welcome. We're thrilled that you've signed up and so excited to be part of your morning routine." We set a really specific. thing from the start in terms of telling them Monday through Friday, it's not a weekend newsletter, it's Monday to Friday. What time it's going to show up in their inbox so they can look forward to it . We give them kind of an outline of what's going to be in the newsletter and kind of the value proposition. They've already signed up, but we're just reinforcing what's going to be there. And then the habit thing that you just highlighted, look for your next email at 7:00 AM tomorrow.

So that way. From the start. They know, okay, this is one I should come back tomorrow. I know if I opened my email at seven there's going to be the next email right there. The other thing that we tried to do too that's been really fun is we added kind of a little bit of a relationship builder, sort of ask at the end.

One last thing. We think Vancouver's awesome, but we'd love to know what you think. Reply to this email and tell us, and they actually do get really interesting replies from their readers who sign up and go, Oh, you know what? I really like this restaurant is event. This is being something that they love about Vancouver.

Those sometimes turn into story ideas. They go out and report. It's pretty amazing. 

Matt Helbig: I really liked how personal this one feels. I think coming from the other one, it's very polished, but this one feels very one to one, a little bit more personal and just kind of paired down and simple. I think it works for this brand especially.

Dan Oshinsky: Something I want to ask you too. I'm curious for your take on this. I typically advise folks to do something like mentioning the, "Hey, you can always add us to your address book kind of thing that help reduce the chance that you might go to the spam folder. Some folks like to add the additional message, drag this over to the primary sort of tab.

I'm curious what your take is. Where does that fit into a welcome message like this? 

Matt Helbig: People have asked us for white listing instructions or examples or something like that. I think this is the right place to put it. Maybe a little bit lower in the email or kind of like the last thing.

I feel like depending on the size of the brand, you might not need to do it. If you have a very good delivery rate already. But if you are seeing that, that might be something, like you said, you want to add to a welcome email or something to get people to whitelist you if you're having those delivery issues.

Dan Oshinsky: It's something I usually advise too, is I tell folks, you can tell them to drag it over to the primary inbox, but if you're not then sending great emails that engage your readers. Gmail and these other inboxes are pretty smart. They will just kick your email back to the folder they think it belongs in if you're not actually driving the engagement you need.

So it's not just a one line kind of thing there. It's actually about building a relationship and sending great emails every time. More folks should actually ask in these welcome types of emails to get people to reply, to get people to engage, because that sort of thing does, we know send a positive signal to g-mail and the other inboxes that these emails are great, and from the start, builds in that relationship.

Matt Helbig: To your point too, setting these expectations about when you should receive it as definitely going to build that as well. So, yeah, great example. I think we have another one from Civil Beat, which I don't actually know a lot about, so if you want to enlighten me, that'd be great. 

Dan Oshinsky: They are a fabulous organization based out in Honolulu.

They do all sorts of amazing reporting around politics. They have a reporter actually based in DC that covers Hawaii. They cover the environment, they cover politics and news in Honolulu, and just do a lot of really amazing investigative stories. If you're familiar with something like a ProPublica, they have a lot of that in their DNA.

And what's amazing is from the start, this is an email from Patty who's their GM. She personally, thanks you for subscribing and then in this initial ask their goal is what I call like a plus one sorta ask. So you've subscribed. How can we get you right now to do one more thing in your inbox?

So you just subscribe and we're going to tell you about events that we have that we think are great. How you can actually contribute and write for Civil Beat. They basically have an op ed type of page that's digital where anyone can contribute and write columns for Civil Beat. They tell you about that.

They also want to mention, because they are member supported from the start, early on, they're not going to see a ton of donations from this sort of email, but why not mention it right now that you can support Civil Beat. Give a gift and help fund an organization like this. 

The other thing that's just phenomenal that I love about this email is that you actually get to see who Patty is and who the team is. So for a small organization like this, they're a newsroom of about 25 people. And so for them, you see at the top of the email, a photo of the whole team, you see a photo of Patty at the bottom. You get a sense that in this news environment too, and people aren't always sure about where their news is coming from.

Who's reporting it, you actually get to see the whole team right there and see the faces, which I think is super, super powerful. It creates an unusually strong personal connection from that first email, and then they go out and do a series of emails over the course of the first 60 days to continue to introduce you to all the different voices on their team.

So you really get to build that relationship. 

Matt Helbig: Another one that where they're very personal and thanking you for being a subscriber. Very informational email. I think it definitely fits with this brand. So is there anything that you might want to improve on this one or test anything? 

Dan Oshinsky: So I worked with their team on this email and on this series of emails.

What I'll say for something like this is for other brands that are thinking about this sort of ask, you might want to think about if you're going to give some sort of plus one message and we want you to go and do now that you subscribed, here's the next step in the journey. Be really, really mindful about what that positive engagement is.

For Civil Beat, something that's a differentiator is they have these amazing events that was a really something they wanted to focus on. They also have a shout out about, you know, Facebook, Twitter, Instagram, that sort of thing too. A lot of brands kind of stop there. Oh, we're on this other channel.

I would really encourage a lot of folks out there who are thinking about saying, you subscribed to our newsletter, you can also follow us on Facebook. I'd say is think about telling someone why they should subscribe to you on another channel. You already have them in their inbox. You have a personal connection.

If you do something special or unique on a channel like a Facebook or an Instagram, you should tell them why they might get a little extra value out of this sort of thing. Say somebody signs up for a weekly newsletter telling them, if you follow us on Twitter, you're going to get hour by hour sorts of updates on what's happening in the news, where that's your source for breaking news, that sort of thing.

Okay, well there's value in that for me. If you are doing something special on Instagram. Tell me. But really be mindful of what you're asking and making sure people understand here what the value is for them if they're going to do one additional thing for you.

Matt Helbig:  And then as you said too, this is from the editor. Do you find that that first email contact maybe from like a person is more successful than a brand name?

Dan Oshinsky: I think it's worth testing and seeing what actually works best for you.So we just showed The New Yorker one that's from a generic New Yorker voice. The Vancouver's Awesome one is just from a generic voice, although many of the other emails in their welcome series pretty much all are from a person after that initial message.

This. Patty and their team. Each one of these welcome emails from a specific person. It's something they've tested and seen good results from. To be honest, there isn't a best practice here. I would test and try and see what works best for you. I personally really like the emails that come from a person, from the start. In particular, someone like this, like a Patty, because you get someone's high level perspective on the organization and it feels nice to be personally thanked, I think, as a reader from somebody who represents the entire organization institution.

But I think it's worth testing and trying and seeing what actually drives results for you. 

Matt Helbig: Yeah. I totally agree. This last one is kind of like a post welcome email a little later in the process, right?

Dan Oshinsky: So this is one with the WBUR. This is just a straight plus one message.

This one goes out about two weeks after somebody has subscribed. So something to say, having this sort of hallmark message is essential for any brand, no matter who you are. You should also think about what the other emails are that go out in the series. What else happens? Cause it's not just a single one off kind of message.

It's a series of emails that you're using to actually onboard someone and build the relationship. This is one that comes out of this for Megan, who's the newsletter editor WBUR, goes out about two weeks after you subscribe and depending on which newsletter you subscribe to, this one goes out to people on their daily list, which is called WBUR Today.

You're on our daily lists. You love it. Here's some other products that are going to compliment your daily newsletter and help you engage even more deeply with WBUR. So in this case, they have an amazing politics newsletter. They have a commentary and opinions newsletter, and they have one around arts and culture in Boston that goes out at the start of the weekend. All products that really compliment the daily. And so here the goal is, let's take you from one newsletter and see if we can get you on two or three and engage even more deeply.

What they and a lot of other organizations I've seen is the more engagement you have, the more likely you are to convert that reader in to, in this case, a donor or sustaining member. Something like WBUR. So driving that engagement. We have you, you're engaged. Let's even get you on one additional email to really, really build that relationship and make WBUR an essential part of your morning routine. 

Matt Helbig: Yeah, I really like that this is a separate send cause I do feel like some brands try to put so much information and content and CTAs in that first welcome email. I think breaking it up over a couple of different sends is definitely smart. 

This one feels like it's very personalized or they recognize that your reader, maybe you've hit the site a few times, you've been getting the newsletter. Now is a good time to ask for these additional signups. Maybe not right away, but now that you've been on the list for a little bit.

Dan Oshinsky: These secondary sorts of emails too as part of the onboarding series, I typically advise folks to think about just making a single ask. So the goal here is, it's been a couple of weeks you subscribed, you've engaged.

The goal here is just get people to sign up for one more newsletter. That's all we're focused on. There's other variations on this email. Certainly organization like that'd be WBUR, which is an NPR station in Boston, they have lots of amazing podcasts. They're responsible for amazing podcasts like On Point and Modern Love.

They could send emails here as part of this series to encourage you to download a podcast too. That's probably a separate sort of thing. If you are a brand, you might be thinking about if you've tried, one feature of something that we have, can we get you to engage a little bit more deeply on a secondary sort of thing. Upgrade to a pro account or test out something that you have. 

Just be thinking about being super, super direct with the ask here because like you said, the more that you try to weave in and cram into a single email, the more that the message gets a little bit muddied. And here it's just a very clear ask. The subject line here is, "Want Even More WBUR Newsletters In Your Inbox?", and they're just really, really clear that the goal of this specific onboarding email is to get you to sign up for more emails.

So all of these came out of a checklist that I built for Not a Newsletter readers. You can go to 2020newsletterchecklist.com and sign up there. While you're there, you can also sign up for Not a Newsletter if you'd like monthly updates from me as well, and I'll share some of my best practices in terms of onboarding, but also other best practices for authentication, testing, all sorts of good things. I built it. It's free to anybody. I remember seeing that Iterable report about 70% of news organizations not having an onboarding series and thought there's an opportunity to teach and learn and share some of this.

My goal is at the end of this year, I don't run into any more news organizations, I don't run into any more brands who say, Oh no, we don't send a welcome email. That's not important to somebody like us. I want, the next time there's one of these reports, I want to see 100% onboarding penetration across the marketplace.

So 2020newsletterchecklist.com sign up and I'll send you some resources to help get started on onboarding authentication and a couple other great things for you in 2020. 

Matt Helbig: I think there's a lot of actionable little tips and tricks in there, so definitely give it a download. Another plug for your email newsletter. It's like the secret sauce. Everybody, it seems, loves it so much. So definitely give that a follow. That one just comes out monthly, right? 

Dan Oshinsky: It comes out once a month, usually the middle of the month. And if you go to notanewsletter.com it'll redirect you towards the Google doc. So you can go and read it and be one of the many anonymous quokkas and rabbits and all sorts of weird Google doc animals that appear on the top right corner when people are reading it. 

Also, I will make a plug just to make sure that we go full circle with this. When you sign up for Not a Newsletter, you get my onboarding series and in one of those emails, one of the resources that I say is, Not a Newsletter isn't enough. What you really should be doing is subscribing also to the Really Good Emails email, because they send really good email too. So we can send people full circle. 

Matt Helbig: Okay. Yes, definitely. Awesome. Well, thanks so much for taking the time today. It was a lot of fun.

Dan Oshinsky: Thanks for having me. See ya.