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Most marketers treat automation like a “set it and forget it” task, but that is exactly how you end up with low engagement and ignored emails. Jay Schwedelson connects with Daniel Murray to break down why the best automated sequences do not look automated at all. They also detour into some surprisingly practical relationship advice just in time for Valentine’s Day.

Follow Daniel on LinkedIn and check out The Marketing Millennials podcast for sharp, no-fluff marketing insights. Subscribe to Ari Murray’s newsletter at gotomillions.co for sharp, actionable marketing insights.

Best Moments:

(01:52) Why celebrating Valentine’s Day a day early might actually be the smarter move

(02:37) How to write automated DMs that actually get replies instead of eye rolls

(03:30) Using GIFs and multimedia to make welcome emails feel less robotic

(04:29) The “Over the Top” strategy of inserting manual emails into automated streams

(06:45) Why sending emails at standard times like 9:00 AM is a guaranteed way to be ignored

(07:15) The power of sending automations at odd hours like 8:07 PM to boost open rates

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Transcript

Daniel: Welcome to a new special series called The Bathroom Break, that extra 10 minutes, you either have to listen to marking tips or use the bathroom or both, but I don't recommend. But that's your choice. This

Jay: collab

Jay: is

Jay: gonna be super fun. We have Daniel Murray from the Marketing Millennials and me Jay Schon from the Do This Not That podcast and subject line.com.

Daniel: Each episode in this series, we are gonna go over quick tips about different marketing topics. And if you want to be in the bathroom, fine, just don't tell us about it. Thanks for checking it out.

Jay: We are back for the bathroom break. I'm here with Daniel Murray, the marking millennial. I'm Jay Sch Delson from Do This, not that.

Jay: And before we get it, we're gonna be talking about. Automation streams very exciting. But what is exciting, I'm curious, is not too far away is, is Valentine's Day. And people that know this about Daniel, extremely romantic guy, he's like Sarah, no Dejak, he, he like writes poems and sings these songs to Ari.

Jay: It's unbelievable. So Daniel, uh, I know you must plan months in advance. So do you really plan seriously for Valentine's Day as it's approaching?

Daniel: I be, I believe like this a cheesy to say, but like I think you should do like what you do on Valentine's Day, like tons during the year anyway for your significant other.

Daniel: So I think there's the romantic of me, but I do, I do think that. It's like a carved out date. So I like to like plan a dinner, get a little gift. Um, this year I want to do like a gift from our son to her.

Jay: Good idea.

Daniel: So like, like something cute like that. So yeah, I do think that I, but I also do think like sometimes it's better to like celebrate the day before or something.

Daniel: You don't get these prefixed annoying menus that they have at that are overpriced. So, um, that's an option as well. Um,

Jay: there you go. I love it. I love it. Well, there you go. You got the, you got the Valentine's advice from Daniel. So let's jump into it though about what we're talking about automations. Um.

Jay: There's a lot of things out there that we all automate. Whether you're a business market or consumer market or whatever, nonprofit, you're automating people, going to a landing page, filling out a form, an email goes out, you're automating, uh, uh, certain social posts go out at, at certain times. You're automating some of your, your, your outbound sales outreach emails, uh, people that didn't open an email, you're sending this, that, whatever.

Jay: So Daniel kind of give us what are some of quick win tips for people's automations that maybe is not on their radar.

Daniel: I think one thing is make your automations feel personal and you could do it in a generic way. So for example, I have this like DM automation in my community that I go say like, I saw you scrolling and, and, uh, I saw your name pop.

Daniel: Up and, and I wanted to reach out and say like, how are, like, how are you doing, blah, blah. And I say like, I'm currently like enjoying the weather in whatever area. Where are you right now? And I get like tons of replies. Like either like, you're so lucky you're in warm weather. Or like. Oh, I know this is automation, but it's, this is really good automation.

Daniel: So like when you're doing automation, always make it feel personal, fun, uh, part of your brand. I think another layer to add on is adding. GIF or, um, multimedia stuff and to, to make it feel like more fun. So like in my welcome ema, I have like a Yoda meme, like, I mean Yoda gif. So it's like do little things like text messages.

Daniel: Now you can add gif in there. So in your automations, add things to make it more personal, more fun, more relevant to your audience.

Jay: Yeah, in general you do a really good job of that. The more that you can make your automations not feel automated, the more that people interact with them and you actually get business.

Jay: Um, and the other thing that we've tested, which is really interesting, is we like to also come over the top on our automation streams with our clients. So our clients up automation streams could be some sort of B2B SaaS product or some sort of, you know, direct to consumer play, whatever that. They have the automation streams already all set up, but then, um, we'll have emails that go out, for example, that are over the top again, in addition to email that'll go out to the same population of people.

Jay: That is really just a one-off written by a human being, uh, email. And we're not pausing the other automations, but we're doing it in addition to, and we looked at. Those scenarios where we just had pure play automation and pure, and then we had automation with kind of some of these over the top where we inserted them and the ones with over the top would do phenomenal.

Jay: They would just get us so much extra. 'cause people are like, whoa, what's this? Wakes 'em up a little bit. So I think you can't just do this, set it and forget it and think it's just gonna be this always on thing that's gonna make you money. Uh, I, I, it just doesn't work that way anymore.

Daniel: I think there's like other things you could do in automation.

Daniel: I think one thing I think people make a mistake is to stop doing advertising to those people. So when they, when they do come in your funnel, having that as a list in your, um, in whatever tool you're using to collect emails, um, and have an automation to funnel that as a. Uh, an audience in your to run educational stuff to so you stay top of mind.

Daniel: 'cause now they've, you've got them in one point of your funnel, now you need to educate them anymore. So do some air coverage type advertising to, and also you can add that as an exclusion list too now to like some other things you're doing as well, um, in advertising. So like, that's another automation to think about is like.

Daniel: Now I can put this in a different bucket of advertising and I can also create an exclusion list for people who are for this part of advertising. So that's another thing that I think about is like how to automate it to keep marketing them on other 'cause. Now you have the email and then. Obviously then another level of automation is if you have like a, a tool that can like get more information about, uh, enrich that data.

Daniel: So having an enrichment automation, so then you can start getting more personalized data and then separating enriched versus not enriched and being able to personalize both those and have an email for unenriched versus enriched people. That's another way, and if you're collecting first party data too, that can help as well.

Daniel: So there's. Some automations I think about as well.

Jay: Yeah, I love all of that. And there are also some simple things that you could do with your automations. I think people miss on, so for example, if you're doing email automations, you got all these different triggers based on what they did or haven't done, or fallen off or this, that, or whatever.

AM or:

Jay: The worst thing you could do is just be checking a box and be like, well. We turn that on, it's going. It's the same thing with social posts. If you're automating all your social posts and then you're not taking the time when they post to actually interact, uh, in that first hour when people are interacting with the posts that you just automated and your company just automated, those posts are gonna be dead on arrival.

Jay: So treat automations like they're not automations.

Daniel: And then there's like tools out there that can have automations be more timely to and more platform based. So like if people are more a text message audience versus email versus um, social, you can more timely hit those people on different types of, and now with AI you can get more in depth with that as well.

Daniel: So there's things that you could do too that are not generic, I think. Generic automations are kind of dead. They know people are gonna do it. You're doing it. So figure out ways to be more personal, more timely, more relevant in the inbox to be even seen by that consumer.

Jay: I love that. So, all right, back to the Valentine's Day thing.

Jay: Do you write poems?

Daniel: No, but I feel like you're a home guy. What do you do about that? What is your move? You, you've been, you've been married for, what, 20 years

Jay: now? I've been married 22 years.

Daniel: See? Exactly. So give, give, give me advice. Tell me what I need to do.

Jay: I'm gonna tell you the advice that I should give my younger self, and it's related to birthdays.

Jay: And Valentine's Day, and I think you already do it a little bit. I used to buy gifts. Okay, I'm gonna buy my wife a necklace or something, and then I would buy it and I'd say, here you go. And she goes, Hmm, not really. Don't love that. And I'm like, oh crap. I don't even know the return policy. I'm like an idiot.

Jay: So now I've come to this place in the last few years, which is great, where I don't, we, we, we shop together. Where I am no longer like surprising her. Exactly. You know, because I am clearly very bad at this. So that's my advice is get on that page. It saves you a lot of pain and heartache.

Daniel: There's two things I would add to that is one, when you're significant other is mentioning something that they want, like document it.

Daniel: Like have I have notes in my phone of like things Ari wants? Um, and then. I slyly bring it up in conversations way before, like, oh, like, oh, that looks nice, like, and like see her reaction. And that's, that's one, one thing is like documented. And second, we had like some of the major like. Like, like store brands out there.

Daniel: I have to login to her account and I tell her to add things to her wishlist on there. So she's always adding wishlists. And so I always, I was like, add things to your wishlist so I know what she likes so I can get things for you.

Jay: That's, that's huge. I'm gonna give you login to like my Amazon account.

Jay: I'll add things in there so you can get it for me. That's my new,

Daniel: oh yeah. I'm gonna start doing that. I, um, salad with salmon is gonna be sent to your office every, every, every week. I can't wait.

Jay: It is amazing. Well, all right everybody, now you're prepared for Valentine's Day. We've really, we've really crushed this.

Jay: Appreciate you all being here. Leave Daniel a review on the marking millennials, or leave me one on do this, not that. You all are awesome. See you The next one.

Daniel: Daniel, come on man. I gotta get back to work. Get out of there all while he's still in there. This is Jay. Check out my podcast.

Jay: Do this, not that for marketers.

Jay: Each week we share. Really quick tips on stuff that can improve your marketing and hope you give it a try. Oh, here's Daniel. He's finally out

Daniel: back from my bathroom break. This is Daniel. Go follow the Marketing Millennials podcast, but also tune into this series. It's once a week, the bathroom break. We talk about marketing tips that we just spew out, and it could be anything from email subject line to any marketing tips in the world.

Daniel: We'll talk about it. Just give us a, a shout on LinkedIn and tell us what you want to hear. Peace out

Jay: later.

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