How to Make Automated Marketing Feel Human | Bathroom Break #93

2 Feb 2026 · 11 min · 4 chapters

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In short

How to make automated marketing feel human, plus practical Valentine’s Day planning banter.

Guests

Daniel Murray (Marketing Millennials) and Jay Schwedelson (Do This Not That, subjectline.com). Daniel’s background/claims: He runs community DM automations that reference a person’s name and current location/weather, generating replies; he adds fun multimedia (e.g., GIFs/memes) in welcome emails. Jay’s background/claims: He and clients test “over-the-top” one-off human-written emails alongside always-on automation streams; those performed better than pure automation.

Notable examples

DM automation (“saw you scrolling… where are you right now?”), Yoda GIF in welcome email, human-written follow-up emails without pausing automations.

Key claims

Avoid generic “set-and-forget” automation; vary timing (don’t all send at 9am), interact with social posts after posting, keep educating via retargeting/advertising, use enrichment to personalize enriched vs unenriched segments.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Valentine's Day Preparations

0:45 to 2:06

Discussion on Valentine's Day preparation and romantic gestures.

“And before we get it, we're going to be talking about automation streams.”

Effective Marketing Automation

2:06 to 6:40

Insights on making marketing automations feel personal and engaging.

“So let's jump into it, though, about what we're talking about, automations.”

Timing and Interaction in Automation

6:40 to 8:11

The importance of timing and personal interaction in automated marketing.

“And there are also some simple things that you could do with your automations.”

Valentine's Day Gift Advice

8:11 to 10:30

Practical advice on selecting thoughtful gifts for Valentine's Day.

“I think generic automations are kind of dead.”
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Transcript

Automatic transcript. May contain errors.

0:07Welcome to a new special series called The Bathroom Break. That extra 10 minutes, you either have to listen to marketing tips or use the bathroom or both. But I don't recommend both, but that's your choice. This collab is going to be super fun. We have Daniel Murray from the Marketing Millennials and me, Jay Schwetelson, from the Do This Not That podcast and subjectline.com. Each episode in the series, we are going to 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. We are back for the bathroom break.

0:41I'm here with Daniel Murray, the marketing millennial. I'm Jay Schwedelson from Do This, Not That. And before we get it, we're going to be talking about automation streams. Very exciting. But what is exciting, I'm curious, is not too far away is Valentine's Day. People don't know this about Daniel, extremely romantic guy. He's like Sereno de Berge. He writes poems and sings these songs to Ari. It's unbelievable. So Daniel, I know you must plan months in advance. So do you really plan seriously for Valentine's Day as it's approaching? I believe, that's what she's going to say, but I think you should do what you do on Valentine's Day.

1:18Tons during the year anyway for your significant other. 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 idea 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 celebrate it the day before or something so you don't get these prefixed annoying menus that they have that are overpriced. So that's an option as well. There you go. I love it. I love it. Well, there you go. You got the Valentine's advice from Daniel.

2:06So let's jump into it, though, about what we're talking about, automations. There's a lot of things out there that we all automate, whether you're a business marketer, consumer marketer, whatever, nonprofit. it. You're automating people going to a landing page, filling out a form, an email goes out. You're automating certain social posts go out at certain times. You're automating some of your outbound sales, outreach emails, people that didn't open an email, you're sending this, that, whatever. So Daniel, kind of give us, what are some quick win tips for people's automations that maybe is not on their radar?

2:37I 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 i saw your name pop up and and i wanted to reach out and say like how 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 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 gifts or um multimedia stuff and to to make it feel like more fun so like in my welcome email i have like a yoda meme like i'm in yoda gif so it's like do little things like text messages now you can add gifs in there so in your automations add things to make it more personal more fun more relevant to your audience 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 you actually get business 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 have automation streams could be some sort of b2b sass product or some sort of you know direct to consumer play whatever that they have the automation streams already all set up but then 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 that is really just a one-off, written by a human being email.

4:34And 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 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. They would just get us so much extra because people are like, whoa, what's this? It wakes them up a little bit. So I think you can't just do this set it and forget it and think it's just going to be this always on thing that's going to make you money i it just doesn't work that way anymore i think there's like other things you could do in automation 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 because now they've you've got them in one point of 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 and advertising so like that's another automation to think about is like 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 that to keep marketing them on other because now you have the email and then obviously then another level of automation is if you have like a a tool that can get more information about enriched that data.

6:21So 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 lists 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. So there's some automations I think about as well. Yeah, I love all of that. And there are also some simple things that you could do with your automations. that 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.

6:54What you don't want to do is like, all right, all of our stuff's going to go out at 9 a.m. or 6 a.m. or 11 a.m. That's a fail. Then you are literally creating wallpaper. People start to get accustomed to the garbage that you're doing. Have automations go out at 8.07 p.m. at night. Have automations do things that are so counter to what everything else is. And that's how your automation is not going to feel like an automation. The worst thing you could do is just be checking a box and be like, well, we turn that on. 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 in that first hour when people are interacting with the post that you just automated, your company just automated, those posts are going to be dead on arrival.

7:40So treat automations like they're not automations. And 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 social, you can more timely hit those people on different types of and not with AI. You can get more in depth with that as well. 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 going to 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.

8:26I love that. So all right, back to the Valentine's Day thing. Do you write poems? No, but I feel like you're a poem guy. What do you do for a Valentine's Day? What is your movie? You've been married for, what, 20 years now? for 22 years. See, exactly. So give me advice. Tell me what I need to do. I'm going to tell you the advice that I should give my younger self and it's related to birthdays and Valentine's Day. And I think you already do it a little bit. I used to buy gifts. Okay, I'm going to buy my wife a necklace or something. And then I would buy it and I'd say, here you go. And she's like, not really, don't love that.

9:05And I'm like, oh crap. I don't even know the return policy. I'm like an idiot. it so now i've come to this place in the last few years which is great where i don't 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 there's two things i would add to that is one when your significant other is mentioning something that they want like document it like have i have notes in my phone of like things are he 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 documenting second we had like some of the major like like like store brands out there i have to log into her account and i tell her to add things to her wishlist on there.

10:04So she's always adding wishlist. And so I always, I was like, add things to your wishlist so I know what you like so I can get things for you. That's huge. I'm going to give you a login to like my Amazon account. I'll add things in there so you can get it for me. That's my new choice. Oh yeah, I'm going to start doing that. Salad with salmon is going to be sent to your office every week. I can't wait. This is amazing. Well, all right, everybody, now you're prepared for Valentine's Day. We've really crushed this. Appreciate you all being here. leave Daniel a review on the Market Millennials or leave me one on Do This Not That.

10:36You all are awesome. See you at the next one. Daniel, come on, man. I got to get back to work. Get out of there. While he's still in there, this is Jay. Check out my podcast, Do This Not That for marketers. 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. Back from my bathroom break. This is Daniel. go follow the Mark and Millet podcast, but also tune into this series. It's once a week, the bathroom break. We talk about marking tips that we just spew out. And it could be anything from email, subject line, to any marking tips in the world.

11:13We'll talk about it. Just give us a shout on LinkedIn and tell us what you want to hear. Peace out. Later.

From the publisher

Most marketing automations technically work…and still quietly fail.

Jay and Daniel break down why set-it-and-forget-it automations no longer cut it and what actually makes automated marketing feel personal, timely, and human.

They cover how to write automations that sound like a real person, why unexpected send times outperform “best practices,” and how layering one-off human messages on top of automation boosts results. 

Plus, what’s the difference between schedule sending at 10:00 vs. 10:14? Turns out, it’s the difference between background noise and getting noticed. 

If your automations feel invisible, ignored, or robotic, this episode shows how to make them feel alive again.

Follow Jay:

LinkedIn: https://www.linkedin.com/in/schwedelson/

Podcast: Do This, Not That

Follow Daniel:

YouTube: https://www.youtube.com/@themarketingmillennials/featured

Twitter: https://www.twitter.com/Dmurr68

LinkedIn: https://www.linkedin.com/in/daniel-murray-marketing

Sign up for The Marketing Millennials newsletter:

https://themarketingmillennials.com/

Daniel is a Workweek friend, working to produce amazing podcasts. To find out more, visit: https://workweek.com/

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