With eight years’ experience of writing newsletters for developers, Peter Cooper has a few secret-sauce tips to share. He gives some practical deliverability insights as well as advice on content that works and practices that don’t in this talk from DevXCon San Francisco 2018.

Transcript

So I’ve actually slightly tweaked this. You can probably get rid of the words “making” and “enjoy” because I’ve actually kind of changed how I’m giving the talk. You’ll see why as I go on. Who was watching the royal wedding the other week?  You watched it, yeah, because I know billions of people around the world watched it. It was a fantastic event. I really loved it. See, there’s someone laughing down the front. It was a good show, wasn’t it? It was fantastic. But the one thing that I kind of took away from it, noticed, was that the pastor, Michael Curry, was using an iPad when he was giving his talk. And I thought if it’s good enough for the royal wedding, it’s good enough for me today. So that’s why I’ve got this here to help me out as I progress without any slides unfortunately. So I’m gonna move fast. Take notes if you are involved in doing email. I’m gonna try and share a lot of things that I have done that have had like a needle-moving effect and some things that have zero effect at all. So take notes if you’re into email. I’m gonna try and share some things I’ve never sort of spoken about before, kind of secret-sauce-type things we’ve discovered.

It’s all in the delivery

So a lot of people like when they look at what I do, which is send emails to 400,000 developers every single week, JavaScript, Ruby, all these different topics…some people who don’t know what I do say, “Are you a spammer, like you send a lot of emails to people?” And I’m like, “No, I’m not.” But there’s only two letters that actually separate me from a spammer, and that is that spammers send unsolicited commercial email in bulk, and I send solicited commercial email in bulk. And this does mean that sometimes there are very similar challenges between the two kind of disciplines if you will, in that we both send email kind of en masse and bulk and we also have to deal with deliverability issues. And that’s something that I particularly wanna focus on today.

So this isn’t entirely about people enjoying the newsletter. It’s about the fact that they even get it in the first place and actually are able to open it. Because being dev rel people I kind of came to this assumption in the last week that you know how to like make things that developers are interested in. That’s like your entire job. So you can take that over to email, but what perhaps you don’t know quite so much about is what things are you doing perhaps that you don’t realize that may be affecting the deliverability of your emails? And that’s something that because I’ve been doing this for eight years, I actually have some opinions and kind of data and insights upon.

So I’m gonna focus on a few things that work and then a few things that just have no impact at all but people think they do. So what works? There’s the best practices. It’s the standard stuff. I’m not gonna dwell on it. It’s things like all the stuff with going to regulations, GDPR and having permission and doing double opt-in and not adding people to lists that they didn’t sign up for in the first place. All that stuff is absolutely essential and I very, very strongly recommend it. You’re gonna end up with spam reports and things like that which once you start getting those en masse, you’re gonna run into trouble straightaway. So please do stick with those things. And also if you’ve got…maybe you’re involved in sending email, maybe you’ve got technical people doing it, make sure that they’re doing SPF, Domain Keys and also that you get a DMARC record for your domain. So these are all very technical terms, but essentially, they stop people from pretending to be you. And a lot of providers, including Gmail, see the technologies and they’re like, “Yes like if you’re using that, you’re more likely to make it through and less likely to end up in spam or even the promotions folder and things like that.”

Where does your newsletter end up?

You also wanna make sure that you’re from fields are really good and that you do like address validation as well. So people subscribe to your list and they put “gmail.con” and things like that. This is really, really common. And if you’re able to clean that up, then great. There are services out there that will do that but you can also…I think there’s like a JavaScript plug-in that will fix some of the most common misspellings as well. So if you’ve got a control of a form on your site, it’s well worth doing that.

You also wanna make sure that everything is mobile friendly. Developers I found are actually less likely to read developer-related stuff on mobile devices, but it’s still important to get it right because that number is increasing. And I know it’s over 50% for standard email in the e-commerce world, it’s not quite so high for developer stuff but you still need to focus on that. So you need to make sure you’ve got a good provider. You got nice warm IPs and that your email system is basically second-to-none. You’re doing everything by the book. That’s very important to keep out of this promos folder. And that’s something that we focused on a lot, like every week, when we send all of our newsletters, we actually set up a raw Gmail account that we send all of our emails to and then we can see which box by default it falls into. And it’s worth creating these new kind of Gmail boxes every several months because sometimes they will learn what you’re doing by clicking on the mails and things and they all kind of rank your mails better. So create fresh ones and then keep testing over time to see what occurs.

There’s a few different tricks that we’ve used. One of them, and this is a slightly dirty trick but actually makes good sense, is that we change wherever we mentioned word “unsubscribe.” We made it “stop receiving newsletters”, “leave the newsletter,” like different kind of terms that you can use for that because there are corporate email systems out there that will see the words on subscribing a mail be like, “Right, that’s an obviously commercial email. Let’s throw it over to here.” And the fact is we’re delivering news like we’re not delivering things that are commercial. We have sponsors in our newsletters, but I don’t tend to think of it being commercial mail per se because people signed up to get news about JavaScript, Ruby, whatever. And the fact that we’ve got a sponsor or two in there, I don’t think necessarily makes it completely commercial.

You do need to watch out with Google though because what gets you in the promos folder is kind of like a scoring process. Now, I don’t have internal information about this but for doing it for several years and testing what’s going on, it seems that it’s not any one thing that will get you in there. It’s not a reputation even with your domain or your email address. But it’s like if you just use bad words or you use, like, all caps too much or you put all caps with exclamation marks on the end, they’re kind of like magnifying effect of like if you had a score that’s a spam score, then it kind of ranks up and ranks up. And once you pass this threshold which varies on a per user basis we’ve discovered, it then pushes you into the different folders. So you need to really tone down a lot of things like exclamation marks and emojis everywhere unless that’s something that you’ve been doing for a long time and you’ve been staying in the primaries doing that.

New domains, too many numbers, business names – they don’t help

You also wanna avoid linking to like really, really new domains. We’ve had people submit news from domains that are, like, one, two days old. That’s gonna guarantee that you’re gonna end up in the promos at least, but often in the spam as well. And we run all types of tests to make sure that doesn’t occur, but whenever it’s occurred, it’s always because there’s been some weird script. Someone’s created an advent calendar for example, they’ve registered, like rubyadventcalendar.christmas. It’s a weird TLD to start with and it’s also only been registered for 24 hours. Like Gmail sees that and they freak out like they really hate that type of thing. So be careful with that type of thing.

You also wanna check that you’re not using too many numbers and kind of business names in the subject of your email. We’ve actually got emails out of the promo folder and back into the primary just by dropping words like Microsoft and Uber and Salesforce and things like that where they’ve been in headlines in the email, but then we’ve put them in the subject line and we just literally get rid of a word or two and it bumps it straight back into the primary folder again. It is that touchy. You really, really need to test.  That’s the one thing I wanna get across.

So I’m gonna quickly fly through some content that we’ve discovered really clicks with people. Obviously we get tens of thousands of people click on all of our different links, and I keep track of all that data in aggregate so I know what works. I know very, very quickly due to time.

What to include

Roundups and best practice lists really, really do well. Heroku did this with their “Habits of a happy note hacker” each year and that means we get to link to each year as they update it. That get tons of clicks. Google does things like “12 best practices for account authentication,” like it sounds kind of boring but people really love those kind of lists especially when they come from sort of authoritative sources.

People always love new features. If you got a new feature in your product, people are gonna click on that. We get that all the time. We had a Ruby 2.5 feature list. You got 21% CTR, which is amazing. Brand new releases as well that Postgres 10, all that type of stuff. MongoDB releases, they always do well. People always like comparisons. So our top link I think ever, we got 14,000 clicks. SitePen did a web framework comparison between React and Angular, and it was kind of like a roundup opinion piece. Those sorts of things worked really well. So if you are able to relate your product to other services in some way where you’re not kind of like necessarily pushing them to competition, that can be a really good way to go as well. And guides as well, so things like the modern JavaScript cheat sheet we link to. It had 11,000 clicks recently, so another popular thing.

I’ve got a whole list of these. Now, I’m gonna take my notes and I’ll make a screenshot and put them up somewhere on Twitter so you can see some of the other things I’ve not had time to get into. So as we get towards the end, I just wanna focus on a couple of quick things. One is that if you do wanna make things that people really enjoy and engage with, get in touch with Kathy Sierra’s “Badass: Making Users Awesome” book. It’s an absolutely amazing book that really digs into how you can use different media to make your users become more awesome and that’s really what it’s all about. It’s not about just picking up your product or your service, or the news in my case. It’s about making them even better.

What to avoid

Things that don’t work. Very, very quickly: Subject lines…I found they have a minimal effect, 1% to 2% open rate. I don’t care. Design – to a point, we’ve changed the design. It almost has no effect ever. Sending on different dates and times, again has no effect, just as long as you’re consistent doing it the same time each week. I’ve talked to people who do it on every single day of the week and they all do well.

And last but not least, the other thing that doesn’t really matter is you do not worry about the haters or people that are heckling you. The only people that matter are the people that you’re kind of friends with and that you respect in the community. If they say you’ve taken the wrong line, listen to them. Don’t listen to people that hate you. One example we had was we had a guy reach out. He said, “You don’t disclose your ads in your newsletters. You suck blah, blah, blah.”  It’s really, really, really like nasty and I imagine a lot of people would hate it and like be very upset by it. I read it. I’ve dealt with lots of these in the past. I said to him. I said, “Oh, what email client are you using? I can see the tags blah, blah, blah, blah, blah.” And I was very matter-of-fact and dry about it. And he emailed back. The next thing he’s like, “I am really, really sorry.” He’s like, “I was drunk, stoned and I received a ton of email today and it made me really upset and I just wanted to take out on someone.” This happens all the time. I deal with about 10 of these every year. So do not listen to those people. There’s gonna be some slightly odd people you’ll run into, the one in a thousand. If you’ve got more than a thousand people, they’re gonna be emailing you.

And so from this one other crazy person, thank you very much. And if you want Q&A, follow me @peterc. I’ll answer any questions you’ve got. Thank you.