Delivering Episode 30: Friends on Email with Caitlin Smith

In this episode of Delivering, host Jason Rodriguez interviews one of his friends, Caitlin Smith, about how she uses email both as an elementary school teacher and your average email user. Listen to learn what subject lines get Caitlin to open, why personalization is important, and how much she uses the different tabs in Gmail.

Episode Transcript

Caitlin Smith:
Welcome to Delivering, a podcast about email design, strategy, copywriting, development and the email marketing industry. I’m your host’s friend, Caitlin Smith.

Delivering is brought to you by Litmus—the only platform trusted by professionals to help you send email with confidence, every time. Over 600,000 marketing professionals use Litmus’ tools to build, test, and analyze better email campaigns faster. Head over to litmus.com to start your free 7-day trial of Litmus, and start sending better emails today.

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Jason Rodriguez:
Very well done. I feel like anytime I have one of my friends record this intro they always do it better than I do, so thank you, Caitlin.

Caitlin Smith:
I’m used to reading a loud a lot.

Jason Rodriguez:
Yes. Yeah. Which I guess that’s a perfect segue into my very first question for you and that is, what do you do?

Caitlin Smith:
I am an elementary school teacher. This year, I’m teaching fourth and fifth grade math.

Jason Rodriguez:
Awesome. How’s it going?

Caitlin Smith:
It is weird.

Jason Rodriguez:
Yeah.

Caitlin Smith:
Seeing the kids every day, and some of them will turn on their videos and some of them won’t, and some of them participate and some of them won’t, and some of them won’t even come to class. It’s been an interesting journey. But then there are some kids who are there and participating and it’s like regular class for them, so ups and downs and just weird.

Jason Rodriguez:
Yeah, that sounds about right. All right, so you guys are still all virtual right now, right?

Caitlin Smith:
We’re still all virtual right now. We are scheduled to head back in-person on Wednesday, October 21st.

Jason Rodriguez:
Nice. Well, good luck with that.

Caitlin Smith:
Thank you.

Jason Rodriguez:
I’ll be eagerly waiting to hear how it goes.

Caitlin Smith:
Yeah, me too.

Jason Rodriguez:
As a teacher, you’ve obviously been faced with having to overcome technical challenges this year. And I know just from watching my own kids, they have a whole bunch of different apps and Google Classroom and Zoom and Hangouts, all this kind of stuff they’re using these days. I’m kind of curious on a scale of 1 to 10, how would you rate your technology skills when it comes to that kind of stuff?

Caitlin Smith:
I’m going to give myself a six.

Jason Rodriguez:
Six, solid.

Caitlin Smith:
Yeah.

Jason Rodriguez:
Yeah. You’re young, you’re my age, kind of a digital native so I guess that kind of comes with that. Yeah, I grew up using the internet, using apps, using smartphones, all that kind of stuff.

Caitlin Smith:
Oh yeah.

Jason Rodriguez:
Yeah, so are you an Android or an iOS user?

Caitlin Smith:
Well, I’m actually a little bit of both because my phone is an Android, but my computer is an Apple. I go back and forth between them just depending on what modality I’m working in.

Jason Rodriguez:
Sure. I’m assuming you’re a Gmail user, just based on where I was sending emails to you?

Caitlin Smith:
Yeah.

Jason Rodriguez:
Yeah. Do you use that through a specific app on your phone or on your laptop, or is that just through Chrome when you’re on your laptop and the Gmail default app on your Android phone?

Caitlin Smith:
Yeah. Those are both exactly what it is, Chrome and the app on my Android. Mm-hmm (affirmative).

Jason Rodriguez:
All right, perfect. I guess how often do you check your email?

Caitlin Smith:
My personal email? Because I’ve got work email and then also personal. My personal email, I would say I check it maybe two to three times a day, and I do get push notifications through my phone so I think it keeps me on it fairly often.

Jason Rodriguez:
Yeah. Do you usually open it up first thing in the morning?

Caitlin Smith:
Yeah. I get a lot of morning emails like the New York Times and there’s some teaching blogs that I subscribe to, and a lot of those do first-thing-in-the-morning emails so I usually open those up.

Jason Rodriguez:
Yeah. How about for work stuff? Is that through Gmail too or is that completely separate through the school’s system?

Caitlin Smith:
Yeah, completely separate. We have actually, interestingly, both a Gmail account and an Outlook account in my district, which is a little bit confusing. But I get all my emails to the Outlook so I just go to the webmail on Chrome and check that a couple of times a day on workdays. And then I also have the other one linked to my phone just to make it really easy for me to do other stuff and check other things, because I have all my apps are linked to the Gmail account and then all of my work emails go to the Outlook. It’s interesting, I’m using it both ways.

Jason Rodriguez:
Cool. Yeah, we’ll primarily focus on personal stuff, but when you check your email then are you usually doing it on your phone or on your laptop?

Caitlin Smith:
On my phone.

Jason Rodriguez:
Okay. Yeah.

Caitlin Smith:
Yeah.

Jason Rodriguez:
Have you heard the term email triage before?

Caitlin Smith:
I haven’t. I could probably make a good guess as to what it is, but I have not.

Jason Rodriguez:
What do you think it would be?

Caitlin Smith:
It would be the automatic sorting that happens. I have a bunch of different categories in Gmail where it goes to, I think it’s promotions and a couple of other maybe work or something. There’s a couple of different categories so that they’re not all in my main email inbox.

Jason Rodriguez:
Sure. Yeah. When I say email triage, I’m thinking of something a little different, but I don’t think you’re wrong in the fact that those different inboxes and stuff in Gmail is kind of triaging that stuff for you. I think that’s a good take on that. But email triage, I guess to me, is when you have an email, like on your phone, and you kind of bookmark it or save it for later to look at in more depth, later on in your day when you have more time or you want to open up on your laptop. Do you ever do that?

Caitlin Smith:
Yeah.

Jason Rodriguez:
What kind of emails do you usually do that for?

Caitlin Smith:
Usually the teacher blogs and I also subscribed to a couple of political email lists, and so those. If it seems really in depth, more than just a general message, if there’s steps of things to do, then I’ll usually bookmark those and go back to them later.

Jason Rodriguez:
All right. Cool. Beyond that stuff, what do you typically use email for?

Caitlin Smith:
Typically, I like to get news. All the teacher blogs, there’s a lot of resources there, so that does come to my personal email as well. I do some online shopping, and so tracking packages and looking for deals with those retailers that I subscribe to; and then sending things back and forth to family and friends.

Jason Rodriguez:
Sure, yeah. When you subscribe to an email list, whether that’s through the teacher blogs or political stuff or news or retailer, what makes you sign up for that email list? Is it existing relationship, is it some offer that they’re giving you for signing up? What’s that thought process look like?

Caitlin Smith:
I think a lot of them originate as some sort of deal in the beginning, and then I ended up seeing that they have pretty good deals regularly. And then I become a member or whatever, or visit their websites more often, and so then I get more emails back from them as well.

Jason Rodriguez:
Okay, yeah. Are there any brands that you’ve signed up for that you actually look forward to receiving their emails?

Caitlin Smith:
Yeah, Growth Collaborative. I have a membership there. I think it’s pretty inexpensive for a year. I get a lot of free shipping. They do a full-size product every quarter along with your orders, and I usually order from them every month because I just like having cleaner, kind of more green leaning products around my house and stuff. Yeah, those I do really get excited for.

Jason Rodriguez:
Anybody else?

Caitlin Smith:
Anybody else? There’s another brand called Wholesome Culture that I’ve purchased some apparel from, and I look forward to theirs. Mario Badescu, it is a skincare, and I love their stuff and I order from them regularly. When they’ve got a deal going on, I love that. And then just the New York Times for news because I get those pretty regularly as well, and that’s my main news source.

Jason Rodriguez:
Nice, yeah. I subscribed to a lot of their newsletters too. Are you getting the daily or the weekly roundups of news or do you get their breaking alerts stuff too?

Caitlin Smith:
I just get the daily and then also I get the race related.

Jason Rodriguez:
Okay. Yeah, yeah. Their kind of pop-up newsletter thing that they’re doing?

Caitlin Smith:
Yeah.

Jason Rodriguez:
Awesome. Yeah. I guess let’s focus on retail stuff for a second because you mentioned a couple of retailers. Would it be safe to assume that you buy something directly because of an email that hits your inbox?

Caitlin Smith:
Yeah.

Jason Rodriguez:
What is it usually that gets you to buy from those emails?

Caitlin Smith:
It’s usually a discount or an offer of free gift with purchase.

Jason Rodriguez:
Okay, yeah.

Caitlin Smith:
Yeah. Because I know I’m going to purchase from them anyway, so having something extra, great, I’ll do it right now instead of in two weeks when I actually need it.

Jason Rodriguez:
Sure. Yeah. Just kind of knowing you, I know you’re a very socially conscious person and it sounds like the couple of brands you mentioned lean towards that as well. But beyond just deals and offers like that, are any of them sending things about social movements or things that are going on in the world or the election or Black Lives Matter or anything like that?

Caitlin Smith:
Do you mean, are the retailers sending something?

Jason Rodriguez:
Yeah, yeah.

Caitlin Smith:
Not really. I would say that maybe some environmental tidbits are included in some of their emails, but it’s never the main focus of them.

Jason Rodriguez:
Okay, yeah. Have you gotten anything from outside of the retailers, or one of those brands you mentioned, something that’s about politics or different social movements or things going on in the world?

Caitlin Smith:
Yeah. I’ve definitely signed up for some email lists as well, like the local Black Lives Matter chapter here and then moveon.org. And I feel like there’s a couple more that I want to say that I would have signed up for their email lists through seeing a post on Instagram from someone or a source that I know and trust. And then I move over to their site, maybe you sign up for their email list, or sign a petition and the automatically enrolls me. I do get things that way. I don’t really look at and/or check those as much because I feel like I’m starting to get a lot of them and it’s a little bit [inaudible 00:12:15].

Jason Rodriguez:
Yeah, I totally see the same thing in my own email and I think a lot of people do. How often would you say that those kinds of companies or organizations are sending emails? Is it every day, is it multiple times a day? What’s kind of too much for you?

Caitlin Smith:
Yeah. I mean, right now, it’s definitely multiple times a day coming from different organizations. I would say each one is maybe somewhere between twice a week and once a day. But because I’ve tangentially signed up for so many of them, I’ve got maybe two to five per day in my inbox.

Jason Rodriguez:
Yeah. I feel like I’m probably doing the same thing where I get those and I kind of glance through them quickly, but generally ignore them unless it’s something super local that I’m actually involved in.

Caitlin Smith:
Yeah.

Jason Rodriguez:
I have any of those really caught your attention or made you read through them or take any specific action?

Caitlin Smith:
Yeah. I’m struggling to remember the name. There’s a bill in Congress or it’s being presented to Congress in response to… Oh, it’s the Breathe Act, that’s what it is. That feels like a really large, meaningful piece of legislation that I think is definitely worth my time. And so when I get emails from them and about events going on and things I can do for that, I definitely pay attention and get involved.

Jason Rodriguez:
Is it anything specifically about the email that sent or is it more that you know about the specific topic and you’re just liable to pay attention to that topic?

Caitlin Smith:
Yeah, I think it’s more knowing about the topic and understanding the importance of it that drives me.

Jason Rodriguez:
Sure. Does the design of an email mean anything to you? Do you care what an email looks like? If something doesn’t look great, how liable are you to read it or deleted it?

Caitlin Smith:
I think that once I actually click on an email, which is not all of them all the time, design definitely matters because readability matters and attractiveness matters. If it’s too long and text heavy, then just move on, right? If there’s attractive graphics or a really nice, clean layout, I think that makes it a lot easier to look through. In some ways, it definitely matters to me if I’ve actually gotten into it. But I do think that for the most part, who the sender is and if it’s an organization that I know and care about, that’s probably more important to me.

Jason Rodriguez:
Sure. Yeah, so that preexisting relationship will trump a bad design if it makes its way into your email?

Caitlin Smith:
Yeah, yeah.

Jason Rodriguez:
Yeah. What kind of subject lines get you to open up an email?

Caitlin Smith:
I think that there’s a lot that do. I remember when “Hello at blah-blah-blah” started and I was like, “Oh, that’s cute. That feels kind of more personal and accessible,” and I really liked that. I think that as long as something feels like it’s been tailored to me and it’s coming from some sort of personalized source then that makes me a lot more likely to click on it as well.

Jason Rodriguez:
Sure, yeah. Have you ever gotten any of those emails that have the regarding the “Re:” about whatever topic in the subject line?

Caitlin Smith:
I don’t think so.

Jason Rodriguez:
Yeah, okay.

Caitlin Smith:
Because I think I would think that that was a reply then I would be really confused about that.

Jason Rodriguez:
Okay, yeah. It’s actually a fairly common tactic in email marketing-

Caitlin Smith:
Oh really.

Jason Rodriguez:
… It’s kind of like a dark pattern that clearly is just trying to manipulate you in opening it, so it’s not something I typically recommend people using. But that’s cool, count yourself lucky you haven’t seen a lot of those in your inbox.

Caitlin Smith:
Yeah, I think that that would kind of flag me to be like, “Wait, I didn’t send them an email. Mm, that might be fishy.”

Jason Rodriguez:
Sure, yeah. Do you know what an interactive email is or what do you think an interactive email might be?

Caitlin Smith:
Hmm, I don’t. I mean, other than having links that click out, I don’t know.

Jason Rodriguez:
Okay, yeah. I kind of describe interactive email as an email where you can take some action that triggers a change in the email. This might be, say you bought something from an online retailer and they send you a feedback like “Give us a five-star rating”, and you click on the stars in there and it reacts to it and says, “Oh, thanks.” Something like that, that happens actually inside of an email, but there’s all kinds of different levels of interactivity. There are some companies that have a full-on checkout experience where you can pretty much start and finish most of the buying process for a product inside of your email instead of going to their website. Yeah, I’m just kind of curious if you’ve ever seen any kind of interactivity, something that allows you to take an action and do things inside of an email.

Caitlin Smith:
No, that sounds really cool. But maybe the star rating, that sounds familiar to me. But being able to do any more than that, no, I don’t think I’ve ever.

Jason Rodriguez:
All right. Good to know, yeah. Caitlin, you’re a Gmail user, they’re kind of doing a lot of work on that front so I wouldn’t be surprised if you start seeing more emails like that. How about countdown timers? Have you seen those in emails, trying to get you to create that sense of urgency for a sale or something like that?

Caitlin Smith:
Oh yeah, definitely for sales. That seems pretty common for sales. They don’t really get me to do that much because if I’m going to buy, I’m going to buy anyway. I think it’s a good function to encourage people and remind them. Because if it says, “The end of today,” people might be like, “Oh, but what day was it sent?” But when you have countdown timer in it, you’re like, “Oh, that’s two hours from now. That means I got to get on it now, try to get that sale.” I can definitely see why those would be effective, but I don’t really know if that works on me and I would check a lot of emails that would have those.

Jason Rodriguez:
Sure, yeah. Do you know anything about legislation governing email marketing?

Caitlin Smith:
No.

Jason Rodriguez:
No? All right.

Caitlin Smith:
None.

Jason Rodriguez:
Have you heard the terms CAN-SPAM or GDPR?

Caitlin Smith:
No.

Jason Rodriguez:
The California Consumer Privacy Act, anything like that?

Caitlin Smith:
No. I mean, that doesn’t surprise me that California would have that though. They seem to have a lot better consumer protections than anywhere else.

Jason Rodriguez:
Sure, yeah. I guess, what kind of expectations, if any, do you have around privacy in regards to your personal usage of email?

Caitlin Smith:
I guess just that it’s password protected so it shouldn’t be viewed by any outside forces, but I don’t know really how that actually works. I don’t really worry about it because, that I’m aware of, I haven’t been hacked and that I’m aware of I haven’t had any identity theft. I feel like where I am right now is fine.

Jason Rodriguez:
Seems safe, yeah.

Caitlin Smith:
Yeah, seems safe enough.

Jason Rodriguez:
Did you know that marketers can track what you’re doing in an email as far as they can see what links you click on, how long you’ve looked at an email, things like that?

Caitlin Smith:
Yeah, I do know that. I did briefly work for a marketing company and so I do know about… Oh God, now I’m forgetting what they’re called, about pixels or something-

Jason Rodriguez:
Yeah. Yeah, tracking pixels.

Caitlin Smith:
… is what it is. Yeah, and so I do know. I’ve seen the ads pop up on other websites that directly are linked to things I viewed or advertisements I’ve clicked on. I know that that’s being followed, which it doesn’t really bother me that I’m being re-targeted for things that I’m interested in.

Jason Rodriguez:
Okay, yeah. Do you feel like companies should be able to share or sell your email address when you sign up for one of their lists?

Caitlin Smith:
No, I don’t.

Jason Rodriguez:
Okay. I agree with you wholeheartedly, even though that’s still a fairly common practice.

Caitlin Smith:
Oh, totally. That happened at the marketing company I worked at. You purchase an email list from someone, yeah.

Jason Rodriguez:
Yeah, not the best practice, but it happens.

Caitlin Smith:
Yeah, right.

Jason Rodriguez:
What makes you unsubscribe from an email lists?

Caitlin Smith:
If I’m getting too many emails. For instance, Redfin, because I picked a housing report maybe two or three times in a week, they started sending me five reports a day. I was like, “Okay, guys, I do not want that many. Thank you.” There’s that. Or if it’s just really outdated, and I go and I’m like, “Am I really still getting emails from that company or that organization? I haven’t been interested in that in years. Why am I still getting this?” then I’ll unsubscribe.

Jason Rodriguez:
For those ones is it, it almost feels like they’re emailing you out of the blue or do they still send somewhat frequently and you just now noticed it?

Caitlin Smith:
Yeah, I think it’s, they probably still send me fairly frequently. But because of have the automatic sorting in my inbox, I’m not always looking through the other categories. And so I will sometimes go through them and just be totally dumbfounded by the fact that I’m still getting emails from an organization.

Jason Rodriguez:
Sure. Yeah. How often do you go through those other tabs inside of Gmail?

Caitlin Smith:
I would say maybe once every one to two weeks.

Jason Rodriguez:
Okay, yeah. Have you ever seen anybody send something that has a message like, “Oh, star our emails or save our email address to your safe senders list or drag us into your primary tabs so that we always hit there.”

Caitlin Smith:
I have seen similar messages.

Jason Rodriguez:
Yeah. Have you ever done that?

Caitlin Smith:
No.

Jason Rodriguez:
Okay. Good to know. I am going to use that answer all the time now because we get constant questions about that. Yeah, good to know. Yeah, I don’t think anybody really does, but people still insist on trying to send those kinds of emails.

Caitlin Smith:
Yeah. Yeah, that does resonate.

Jason Rodriguez:
I guess, yeah, we can start right in wrapping up here. I’m kind of curious, what you would tell email marketers to do to make email more valuable for you?

Caitlin Smith:
Hmm, that is a very good question. Especially having been in the field for a little bit of time, I feel like I maybe should have already considered this for myself. I think it has to be quick, easy messaging where something is actionable and clear. Because something that’s long and wordy is not going to help me if the subject line is three sentences long. What am I going to do with that? I think short subject lines that give purpose and, yeah, are actionable.

Jason Rodriguez:
That makes sense. I like it. Yeah. Do you feel like that’s across the board that should just be a trend, like you don’t feel like you have time to devote to your email or that’s just kind of your preference for how to consume things?

Caitlin Smith:
Yeah, I’m not sure. I think it does depend on the audience. I am a digital native, like you said. I’ve had an email address since I was 10 probably, 10 or 11. And because there are so many things I’m interested in and/or need and I’m getting so many emails, it has to be quick and to the point, otherwise it’s just going to get skipped over.

Jason Rodriguez:
Cool. Are you comfortable sharing your very first email address, what that was, because those tend to be have interesting ones?

Caitlin Smith:
Oh yeah. Yeah, it was a Hotmail account, of course. And it was catmo315. C-A-T, which is a shortening of my first name; M-O, which is the shortening of my middle name, and then 315 were just my favorite numbers.

Jason Rodriguez:
All right. Yeah, that’s not too bad. My first one was senorguitar@yahoo.com because I am a Rodriguez and a señor, I guess, and I love playing guitar. And then I also had buddhabass01 at one point because I was a teenager and played a lot of bass guitar and was very into Eastern philosophy. Yeah, any embarrassing ones [crosstalk 00:26:28], are you pretty safe?

Caitlin Smith:
Yeah, they’re all pretty embarrassing. They’re like a silly nickname and some numbers.

Jason Rodriguez:
Yeah, yeah. Yeah, I mean, that’s par for the course for people that grew up in the 90s and early 2000s like us.

Caitlin Smith:
Yeah. I think that that’s really the only silly one I had and I kept that through my teenage years. And then when I got into the workforce in my early 20s, I was strongly recommended to just have my name @Gmail.

Jason Rodriguez:
Yeah. Yeah, that’s smart. Yeah, a little more professional.

Caitlin Smith:
[inaudible 00:27:07].

Jason Rodriguez:
Yeah. Any good books or Netflix stuff that you’re watching these days that you’d recommend to everybody?

Caitlin Smith:
Ooh, let’s see… Netflix. Oh, I saw the funniest Halloween movie. I think it was either called Vampires Versus the Bronx or the Bronx Versus Vampires or something. A lot of very unsettled social commentary about gentrification, so that was really fun and funny, which I enjoyed.

Caitlin Smith:
And for books, I’m actually in a book club and we just finished Between the Worlds and Me by Ta-Nehisi Coates. It’s an anti-racism book club, and I had actually read it in graduate school and revisited it. The messaging and the peek into the life of a personal story of a black man in America was really interesting, and I think just a really good, relevant read right now.

Jason Rodriguez:
Nice. Yeah, and you’re also in another anti-racist book club, which I guess is kind of an anti-racist podcast club at this point with my wife, [Mallory 00:00:28:25]. you guys are going through the 1619 podcasts, which is excellent and well worth the listen.

Caitlin Smith:
Yeah, it’s actually the same club, but we go back and forth between formats. Will do books, we did the 13th, or sorry, 13th on Netflix. Now we’re doing the podcast, and so we’re just open to any media format, but the theme needs to be anti-racism.

Jason Rodriguez:
That’s awesome, yeah. I guess I thinking through the next year, what would be your one hope for something good to happen in the world?

Caitlin Smith:
A COVID-19 vaccine.

Jason Rodriguez:
Okay, that’s a good one. Yeah.

Caitlin Smith:
Or just everyone agreeing to actually stay home for a month so we can get rid of it.

Jason Rodriguez:
I like that, yeah.

Caitlin Smith:
It’s rough, but I think we could do it.

Jason Rodriguez:
I think we could too. I think we need, at the national level, a little support and encouragement for us to actually do that, but…

Caitlin Smith:
Yeah, some real leadership would be [crosstalk 00:29:36]-

Jason Rodriguez:
… Yeah. Well, we’ll see what happens come November. Awesome. Well, Caitlin, thank you so much for letting me pick your brain about email marketing.

Caitlin Smith:
Yeah, I hope it was helpful.

Jason Rodriguez:
Yeah, it definitely is. In this industry, I feel like people, we talk about and think about email marketing on a daily basis, but what I’ve been finding just by talking to family members and friends is that people don’t really think or care about it as much as we do, which is a little bit discouraging. But I feel like that’s probably the case for most industries that you’re not actually a part of.

Jason Rodriguez:
But yeah, it’s good hearing straight from you that you don’t check the different tabs in Gmail that often or the message to drag you to open the primary tab, it just doesn’t work. I think that’s good for people that do listen to the podcast to hear that kind of stuff too, so hopefully we stop wasting time worrying about that kind of stuff and focus on making emails more succinct, more personal and just all around more valuable for people. Thank you.

Caitlin Smith:
Yeah, you’re welcome.

Jason Rodriguez:
Awesome. Maybe we’ll have you back on in a year so and pick your brain a little bit more after these questions have been sitting in there for a little while.

Caitlin Smith:
Gotcha. Gotcha. All right. Well, good.

Jason Rodriguez:
Awesome. Well, thanks. Stay safe.

Caitlin Smith:
Thank you. You too.

Jason Rodriguez:
I’m curious to see how going back to in-person learning goes for you. We’ll definitely have to catch up soon.

Caitlin Smith:
Yes, we will have to see how that goes. I will report back.

Jason Rodriguez:
All right, sounds good.

Jason Rodriguez:
All right, that’s it for Delivering. Again, Delivering is brought to you by Litmus. It’s the only platform trusted by professionals to help you send email with confidence every single time. Over 600,000 marketing professionals use Litmus’ tools to build, test and analyze better email campaigns faster. Head over to litmus.com to start your free seven-day trial and start sending better emails today. And as always, be sure to subscribe to Delivering on iTunes, Spotify, or anywhere you listen to podcasts for future episodes, and join the conversation over on Twitter using the #deliveringpodcast. Cheers.