[00:00:00] Zack Katz: Are your emails engaging your audience? Are you standing out in inboxes that are flooded with noise? In this episode, we uncover the secret to building trust, preventing churn, and crafting emails that make subscribers feel. We'll explore the delicate balance between frequency and relevance, and find out why storytelling may be the most powerful tool in your email inbox toolkit.

If email feels like a struggle, and let's be honest, it often does, This episode is for you. Welcome to WP Product Talk.

[00:00:33] Matt Cromwell: This is WP Product Talk, a place where every week we bring you insights, product marketing, business management and growth, customer experience, product development, and more. It's your go to podcast for WordPress product owners, by WordPress product owners, and now enjoy the show.

[00:00:55] Zack Katz: Hello, everybody. I am Zack Katz, founder of GravityKit, Trusted Login, and DataKit.

[00:01:01] Amber Hinds: And I am Amber Hinds, CEO of Equalize Digital.

[00:01:05] Zack Katz: And today we're going to be discussing emails, email marketing, and emails. And, that is why we have been invited Adrienne Tobey today. Adrian, welcome, and please introduce yourself and what you do.

[00:01:18] Adrian Tobey: Hi everyone, my name is Adrian. I am the CEO and founder of Groundhog, which is a CRM and marketing automation plugin for WordPress. And, I've been doing email, For a long time, and I have some opinions about it, so maybe we'll talk about some of those.

[00:01:34] Zack Katz: Yeah,

[00:01:35] Amber Hinds: Why is this important, Adrian?

[00:01:37] Adrian Tobey: Email is the only uncontrolled channel of communication left. It is the only distributed, democratized channel distribution. Social media, you don't own it. YouTube, you don't own it. And mail, we don't own it. That's controlled as well. So email is really like the only thing that no one can really prevent me from getting a message to somebody else, right?

And even then, Gmail and inbox tools are trying to clamp down that a little bit. But if you have access to an email server, you can communicate a message. And being able to do that effectively, I think, is really important. A lot of people think. Build it and they will come if you have a website, right?

You put some blog posts out there or whatever. It's incredibly difficult to maintain a level of consistency and distributing your message unless you have access to a list. And Running a CRM and marketing automation company myself and providing tools to people to communicate with the list, I just see a lot of bad habits and I want people to be successful with communicating their message.

So I think talking about how to do email better, I think that's important.

[00:02:50] Zack Katz: And what do you mean by bad habits?

[00:02:52] Adrian Tobey: Well, there's lots of different ideas about email marketing strategies. I see lots of different kinds of uses of subject lines, lots of different types of content that people send. for example, a bad habit might be just absolutely stuffing your content with an inordinate number of call to action buttons just to try and get someone to click something.

Too many links. Super image based email templates, right? Not particularly, effective on mobile or if now we have with Gmail, you have to approve images. So if you're sending an image based email, it's like, Oh my God, this email is empty. What gives, right? So it's just lots of things that I think don't really move the needle for businesses that are trying again to communicate a message.

Now. There's a time and place for every email, but an over reliance on one strategy, I don't think is going to get people the results that they want. And some of the strategies that I'll share today I think are going to help businesses move their message a little bit more effectively and gain a little bit of ground in the inbox.

[00:03:57] Zack Katz: Yeah, I think that email, your point about the one type of email is a good one. At GravityKit, we try to mix it up, so that we have, an email that's, more graphical in combination with text, but then an email that's more informational than an email that's time based and requires, immediate action.

And that if you send one type of email, you might get one type of result from it.

[00:04:22] Adrian Tobey: Yeah, precisely. we all know a company that the only email that they send is 50 percent off Friday only, and they send that every week, Or it's this discount expires in three days, and the only thing that they do is like, when they get an email, they just bombard it with offers.

Deals, sales, and the only thing they're trying to get you to do is just buy. If that's the only thing that you're sending, what are you training your subscribers? You're training your subscribers to expect that's the only level of content that you can provide in the inbox.

And if that's the only content they can expect, if they get tired of that They're just going to stop opening them eventually. They might not unsubscribe, but they're just going to they're going to see the subject line come in. It's oh, that's just going to be an offer.

And they're not even going to look at it. If you have a consistent level of variety, keep your subscriber guessing. They don't necessarily know what they're looking for. So there's a little bit more curiosity.

[00:05:18] Amber Hinds: Yeah. I think on that same note, there are some people that only send emails at certain times of year, right?

Like we're coming up on Black Friday. And I know I'm going to get a bunch of Black Friday emails from people that you haven't heard of. I didn't even know I was on because they don't have any sort of regular communication aside from Black Friday.

[00:05:44] Adrian Tobey: Yeah,

[00:05:44] Amber Hinds: That's when everybody like

[00:05:45] Adrian Tobey: warms up their

[00:05:46] Amber Hinds: Yeah, so I do feel like for us as product owners, having this feedback This holistic picture of what does our email communication look like across an entire year and what types of emails do we want to send and how do we want to engage with people? And almost like you think about your brand tone or voice for blog posts.

I think you really need to think about what your tone and voice is in your emails and, what kind of impression you want to give with those. I like what you said, about how it can't just be about sales. There needs to be some sort of value, and that's what's going to keep people interested.

[00:06:26] Adrian Tobey: Absolutely. Email, like any channel of communication, is all about relationships, right? And relationships can't be one sided, There has to be a give and take in a relationship. what are you giving in order to maintain the relationship with your subscribers in the inbox, right?

Offers don't count. That's taking, right? If you're, if they're giving you money that's the one way street. That's them giving you something. So what are you giving back? And doing that over the course of a full year is essential. And you mentioned Black Friday's coming up. It's essential to actually being successful when Black Friday rolls around, which is a particularly difficult time to get seen in the inbox, because that's when everybody goes and warms up their stale MailChimp accounts, and ah, this list is probably still active, like those emails still address, and then, or they're buying lists, or they're participating in all kinds email shenanigans.

[00:07:22] Zack Katz: I would subscribe to a newsletter titled Email Shenanigans,

[00:07:25] Adrian Tobey: That's gonna be the subject line of my next email

[00:07:27] Amber Hinds: email shenanigans. Did you willingly subscribe to that, or did they find your email address and subscribe you?

[00:07:33] Adrian Tobey: Yeah, but who knows? I get As my email address is not particularly private.

Like being an email guy, I'm just, I just get subscribed to stuff. I'm like, Oh, that's interesting.

[00:07:45] Amber Hinds: You subscribe to emails because you want to see what the company's email strategy is, right?

[00:07:52] Adrian Tobey: There's a cool tool for that actually, which escapes my mind at the moment.

[00:07:56] Amber Hinds: RSS feeds.

Courtney Robertson told me about this at WordCamp Canada, and I totally forgot, but you can subscribe to RSS feeds for blogs or email newsletters, and then they won't be in your inbox, but you can go see a feed of all the emails that are being sent.

We'll ask Courtney to, come comment on this video.

[00:08:16] Zack Katz: I'll make a note of it. And while I do that, Adrienne and Amber, I'd love to hear how you, How do you warm up your list? How do you get people engaged with the content that you're trying to, share with them?

[00:08:29] Adrian Tobey: So It's all about value. What are you providing in exchange for their time? Because when you send an email, what you're asking for is I want you to invest a certain amount of time into reading it. And so what is the outcome of you reading it? Is it going to just be an offer?

And am I just asking you to buy something? People aren't particularly interested in that unless they're already at a high level of buyer readiness, right? Are you going to learn something? Are you going to become informed about something? Are you going to feel something? Are you going to be entertained by something?

Like whenever you're writing an email, When you sit down, you're like, okay, I want to communicate something to my subscribers. what are they going to get in exchange for the time that I'm asking them to invest in reading it? And that's how whenever I sit down to write, it's like, what do I want them to take away from this?

So when I've started email is hard, which is like my newsletter of which I've only wrote six so far this year, but they seem to do well in terms of engagement and revenue. I sit down and okay, I have these opinions about email and I want to share these opinions and I want people to actually have better experiences sending emails.

So that's what I want them to take away from it. And I feel like that. is fair reciprocity in terms of their exchange of time, right? And that's what I think it's just all about what are you giving back, right? but you have to be giving something that's actually worthwhile to them.

And things that are worthwhile, education, entertainment, feeling, Thought, anything thought provoking, stuff like that. I love asking people really hard questions. And I love giving really controversial opinions. Because those are two things that I want to engage with, right?

We all have our, ideal customer. We think of our ideal, customer profile and my ideal customer is someone who's, got the gears turning inside, right? And so how do you get people's gears turnings? Ask really thought provoking questions and ask really tough questions or give controversial answers.

[00:10:26] Amber Hinds: Or do you make people open the email to get that, that controversial or thought provoking question?

[00:10:33] Adrian Tobey: I think that depends on the audience. There's no one size fits all for, the email subject line strategy. we could talk ad nauseum for hundreds of hours about what constitutes the perfect subject line.

But the original question was, how do you warm up? Your audience. And when you first get a new subscriber, you send them that initial email. that initial email has, here are your next steps, go follow us on whatever, here's a little bit of value, right?

And when you get that subscriber first, you're training them on what they expect from you. And so if you're asking questions of the subject line or whatever, that's what they're going to learn from you.

And so whatever you're doing as a long term strategy is what you should continue to do as a long term strategy as long as it's producing the best results for you, right? But it starts early when you get that new subscriber, you train them on what sort of the way it works, You have to guess it from the picture on the book. Same thing with emails. It's, there's no one size strategy. It's just whatever you're training your audience on how they can interpret your emails or consume your emails.

[00:11:39] Amber Hinds: So let's be really concrete. I want to know what, if I join Groundhog's email list, what am I going to get that warms me up and makes me stay and tells me what to expect?

What exactly do you do?

[00:11:53] Adrian Tobey: So the first email that people generally get is, you're in start here, right? If they're like downloading the, the plugin, for example, right? Cause there's different ways that people get into my list. Like they can download the plugin and they can opt in through like our onboarding or they can like subscribe and like the footer of the website.

So there's, depending on where people come in, you also want to give them like a different journey. It's not, again, it's not one size fits all. There's a form in the footer of our website that says subscribe and discount. So the first email they get. is a discount because that's what they asked for.

You want to give people what they asked for, right? If they ask to download the plugin, the first email they should get is whatever they asked for. It's here's the link to download the plugin, right?

[00:12:30] Amber Hinds: sequence after that?

[00:12:32] Adrian Tobey: Pardon?

[00:12:33] Amber Hinds: Do you have a direct sequence after that?

[00:12:35] Adrian Tobey: You got to have a Drip Sequence after that. If you don't have a Drip Sequence after that, you're just leaving money on the table.

[00:12:40] Zack Katz: to be clear, a Drip Sequence is just instead of one email, it's a campaign of emails that are scheduled, ahead of time.

[00:12:46] Adrian Tobey: Yeah,

[00:12:46] Zack Katz: Until they unsubscribe,

[00:12:47] Adrian Tobey: basically.

[00:12:49] Amber Hinds: Or that specific drip in. And they get moved into some other kind of communication, right?

[00:12:55] Zack Katz: The

[00:12:58] Adrian Tobey: drip is ongoing when you do like your broadcast emails or, you have like topical things that you just send out to the whole list every once in a while, right?

[00:13:06] Amber Hinds: What do you do, Zack? How do you warm up your list? When people join.

[00:13:10] Zack Katz: Yeah. We do have different warmup lists, depending on where they sign up. So if they sign up through our newsletter, then we welcome them. And, we sign them up for our newsletter. If they come in through our demo website, we do have a drip sequence that I believe is eight emails long.

And it shows in the header in the subject line that is, one out of eight, two out of eight, so that they understand what they are getting. And I know from my own experience, if I. I'm receiving a DRIP sequence and it seems interminable. I will cancel and unsubscribe because I don't know if this, email is going to just haunt me forever.

So Have you

[00:13:47] Amber Hinds: ever A B tested that?

[00:13:50] Zack Katz: believe we have. Here's a wild, A B test that we did with our actual, weekly newsletter. We sent out a newsletter, that had in square brackets, Newsletter. And then the name of the newsletter. And we sent it out without that.

the one with square brackets, newsletter actually performed much better, which was completely counterintuitive for us.

[00:14:11] Adrian Tobey: That's funny. That's a good one. So when, for like our email is hard newsletter, we do plays on like email is hard or like the last, I just, I sent one out this morning ahead of this called email is scary, which talks about using fear as a marketing tactic, which I asked like post status about and posted on Twitter.

I got lots of Great responses from community members. I think Zach, I don't, I'm not sure if you actually commented on that, Zach, or

I am off of Twitter, I got lots of different responses from like people some people said absolutely not under any circumstances.

Some of them said, yeah, but you got to do it right. Some people said, go for it. So I got a wide range of responses, but the point of bringing that up was in the subject line, we just say email is. Insert adjective, part, whatever, because it's part of the series. And, so people, again, we trained people.

When we sent out that first one, it was email chart part one, because I knew that I wanted it to be a series. And so now they're trained to engage with part two, three. So I don't have to do anything fancy in the subject line, right? They know, it's okay if I'm invested in this, of which I've created.

And so that's what they know to look for when I send that email out.

[00:15:22] Zack Katz: And Amber, what do you do? How do you approach email?

[00:15:26] Amber Hinds: So we have a couple of different buckets that people can enter our list. So there's the obvious ones, which is they got the free plugin. So we have the free plugin available via EDD on our website.

we don't ever send people anywhere else to get the free plugin. We say, get it off our website so that we can get their email address. And those get a seven email, drip sequence that is very much here's how to use it, Come to our meetup events, like here's a free ebook you might find interesting.

It's very much about value. It's not really until the very end that we're like, oh, by the way, there's a pro version of this plugin. So they get that kind of warm up. Obviously anyone who comes in off of, Some of our lead magnets that we have on our website, which are like e books, or, if I give a talk, like my page builder accessibility thing, if people wanted to access the Google sheet with all of the data, they had to submit their email in order to do that.

And that actually drove a lot of signups and worked really well for us. those ones don't necessarily get entered into a DRIP sequence right away, then they get dumped on like the main email list, but we also have been experimenting.

with how we can better warm up our two cold ish audiences. One of which is when we sponsor events where we get email lists of attendees who have opted in, like they've said, share my information with sponsors, and then we get it. Like WordPress Accessibility Day, for example, we were sponsoring at a level where We got what ended up for us being almost 600 new people who were not on our list before and they'd attended an event about WordPress accessibility, so we're like, okay, these are really good, but we don't want to just dump them on the list.

So we have this sequence where, again, we try to provide value. So our. Events and meetup has worked really well. So we'll frequently be like, Hey, here is a talk that is coming up in the next couple of weeks that we think will work for you. So it's not just like a generic come to meetup. It's literally like what we'll look at what we have coming up and we'll try and invite them to that because then once they come to a meetup, then they get added into our regular email newsletter sequence,

Here's our email newsletter because that's unsubscribed really fast, right? And then we have the same, that other cold bucket is we have been doing some experimentation with, List building and paying someone on Upwork to build lists. And again, we don't put them on our email newsletter, but we build like targeted campaigns that my partner, Chris writes, and they come from him cause he handles all of our sales.

So he would be the person that we ideally want them talking to if they're going to talk to us about a service, but really we're trying to drive them to the product side. Like we'll find an event that we think they might be interested in and tell them about that. We might share one of our ebooks and then it won't be like go here and enter your email, just download it.

It'll literally be like here's a link to the PDF so you can just get it because we can click track, right? And they get all this scoring in our CRM. And based upon, did they open, did they click, did they do certain things, and then, they might end up getting an actual, phone call outreach and that kind of stuff, but our primary goal is to get them to engage with us in some other way, typically by attending an event, and then they get moved into, our email newsletter sequence, or downloading the free plugin, is a big push with those as well, at which point they get pulled out of the cold email sequence and put into the welcome sequence for the plugin.

So we have a lot of these different ways that we try to warm up depending upon how they came in, but I do think it's really important. A lot of companies I've seen, and I mean we saw this with another WordPress Accessibility Day sponsor, because I put myself on that same list so I can see what people send, what our sponsors are sending to attendees, and it was like, They obviously just took the list and dumped it in their email newsletter because then I got two email newsletters for them in a week and I was like, I bet their unsubscriber rate on this is really high.

You have to have this, a more personal email. And our emails almost never include images. They're like text only. We format them so they're not in a 600 pixel container that's centered. they scale just like if you had written it in Gmail, and then we use our CRM, is able to log into our Gmail accounts and set like it, it will show in our sent box.

It will look like we wrote them an email, as long as we make the content. Personal enough.

[00:20:08] Zack Katz: And it's not accessibility, purpose behind that? Or is that, an attempt to make it look more personal?

[00:20:15] Amber Hinds: It's not really an accessibility thing, although I will say not including images and a bunch of large headings is helpful because then you don't have to spend time.

No, it's more about, we did some testing and we did a lot of this with customers and clients back when we were doing more traditional marketing services. And we just saw so much higher engagement off email, newsletters. and email what kind of looks like one to one emails that just look like regular emails.

So the whole not having it centered, that is literally we want it to look as much like a human being sat in their Gmail and wrote them this email as possible. Yes, it might still have an unsubscribed link in the footer. Everything else about it the signature is identical to our signatures, like the font, everything is the same.

And we just have seen that there's a lot more engagement and responses on those like reply backs.

[00:21:13] Zack Katz: I'd love to hear your take on this, Adrienne, because we do have a mix of email formats during Black Friday because we understand that people might respond differently to the container email versus the email that feels more personally written.

I also feel like there's a high chance of screwing it up if you make it look like it's personally written. You have a merge tag that's not quite right where like the name doesn't make any sense or it looks bad and then it seems like it's a personal email.

[00:21:39] Amber Hinds: I got one today from our kid's dentist that was like, don't lose your dental benefits and it was like, you have zero dollars.

[00:21:48] Zack Katz: I always wanted

[00:21:49] Amber Hinds: to forward it back to them and be like, ah, this is a total fail.

[00:21:53] Zack Katz: So that's my point. Adrian, what do you feel about like personalized emails and how that might backfire or is it worth the possibility of a backfire?

[00:22:00] Adrian Tobey: that. Again, it depends on the audience, right? Like if for product people like us, we have a fairly high level of awareness of the kinds of emails that we get. We know that someone didn't actually sit down and write them. We know that it's from a CRM using merge tags, right?

And there's a certain level of awareness that we have when we get emails from people that look personal, and we know that they're not, right? And so we call bullshit, and that makes us feel icky, right? Not every audience has that same level of awareness, and so there's certainly something to be said for, all right, you want to make it feel personal, and you are at the end of the day if it comes from a genuine desire to help somebody out or to share and empart knowledge or to provide a useful and valuable service.

I don't think there's anything particularly wrong with trying to make it look like it came from a real person If that's what helps them interact and engage with that. if your audience like my audience, for example, I don't bother with that because the people who I'm trying to sell my product to have a high level of awareness.

I do whatever I feel is right to best format the point, right? To, if I have something that I want to convey, I come up with the best, Design that I feel convey that point with headings or images or plain text, full width of the inbox, whatever is the best way to convey that point.

It all depends, I think, on your subscribers level of awareness. If you do the same thing every single time, that's just going to train people that there's zero variety. And then they're going to lose interest and they're going to unsubscribe and there's not going to be emails anymore.

Variety is important. Tone, tonality, personality is important. I think one of the huge missed opportunities that most businesses suffer from is that their emails come from sales at or come from desk at or come from company at whatever, right? And it's like the super professional corporate speak, right?

And like we at, Epic Plugin Company, want to help you do X. And I think that's a huge missed opportunity because people engage with people. People buy from people. People have relationships with people. People do not have relationships with companies. I don't think companies have personalities.

[00:24:23] Zack Katz: what do you do?

[00:24:24] Adrian Tobey: People have personalities. All the emails at Groundhog come from me personally.

[00:24:29] Zack Katz: All of them.

[00:24:29] Adrian Tobey: It comes to my inbox. If it replies, it comes to my inbox. I see it. I read it. I'll reply back. That's what I do.

[00:24:35] Zack Katz: See, here's, that's the thing for me is that I ideally would like to do that and I am also a terrible emailer. I do not respond timely to email and Amber, I'd love to hear what you have to say about this.

[00:24:47] Amber Hinds: I have a solution for this. One of my clients did it back in the day and it was so smart. Her actual email was first name at company.

The emails that she sent were first name, dot, last name, at company. And her team logged into that email box and responded to all of the emails, but it still came from her as opposed to marketing at or sales at or whatever. It looked like it was coming from the CEO and from a CEO's email box, but it was not like the actual email that she used in her day to day business.

It was just a different version of her name. So for me, I

[00:25:30] Zack Katz: don't want to have the team need to log into another tool. We don't use Gmail, we use HelpScout. I could set up another HelpScout inbox and turn off the autoresponder, because we currently have inbox autoresponder turned on. So if people reply to the emails that we send from hello at gravitykit.

com, that gets forwarded to our support team, and they get an autoresponder, which doesn't feel right. Maybe I should set up another inbox

[00:25:55] Amber Hinds: There's Zack Katz, so it's got two K's,

[00:25:57] Zack Katz: Zack. What's that, Adrienne?

[00:25:59] Amber Hinds: We do a mix.

of emails were, some come from me. They're, and they're from Amber at, so if someone replies, it will come to me. A lot come from Chris at, my partner, Chris, cause he does our sales. Our email newsletter come in, the name of our email newsletter is Focus State. So it comes from focus underscore state at, we occasionally send from sales app, but it's pretty, it's like really rare.

It's One or two of the Black Friday sales emails will come from that, whereas the rest will come from, us personally. we try to mix it up, too, because the thought is, if someone has blocked an email address in their inbox, right? You don't want your entire Black Friday campaign to come from So then they get different ones that look different, that come from different, like the sales at one might have an actual banner image

[00:26:47] Zack Katz: There's no way to talk about marketing and not sound mildly evil. So it's not you, Amber. It's the whole idea.

[00:26:55] Amber Hinds: Yeah. We have a meetup at that, like our meetup event reminders come from. And on that front, we're working towards having different lists we used to just send our newsletter and our, Event reminders to the same email list.

And then we realized even though there were preferences, people just unsubscribe. They don't say, no, I want to hear about this. So we're like, no, we actually have to have different lists because maybe they don't want the weekly newsletter, but they do want to hear about an event or vice versa.

we realized we had to have separate lists. So people wouldn't, they'd only unsubscribe from that one list and not

[00:27:28] Zack Katz: Yeah. How do you handle that, Adrienne?

[00:27:30] Adrian Tobey: Groundhog which is what we use, has an email preferences center where you can set up, I want to unsubscribe from these specific topics or they can just But do you find people do

[00:27:39] Amber Hinds: Or do they just unsubscribe from all? People do that, yeah. Because we had that too. And I felt like people weren't going through the effort of choosing preferences.

[00:27:48] Adrian Tobey: my personal opinion is that if they don't want to go through the effort of choosing the preference of the blanket and subscribe, you should respect that.

That's my opinion. if they block the one email, that means they don't want emails from your company or they don't want emails from whoever. my personal opinion is to respect that because I think trying to skirt around that, is to the detriment of the message.

if the message was good enough, or the content was good enough, or the relationship was strong enough, they wouldn't have done that in the first

[00:28:15] Zack Katz: place. But here, what about deliverability? And we're in an age of AI and Google automatically saying if something's promotional or important, and they don't always get it right, How, when the email providers have so much power over the message that does get to your customer and categorizes it for them and determines whether or not it's even worth their time to read, how does that affect your opinion on that?

[00:28:41] Adrian Tobey: Inboxes. Like Google, Yahoo, iCloud, they know how your subscribers consume your email. They know how long you open it for, they know if you open it or not, It's like Google, they have Google Analytics for the inbox.

if you go to Postmaster Tools, you can get a little glimpse into that. And that's how Gmail's engine, is able to categorize your emails. So it's all based on interaction. if your emails are getting decent and good interaction, then You're going to get better engagement and responses.

But if your emails are poorly written or whatever, and it's your audience doesn't consume it in a way, then maybe it's time to rethink your content strategy or rethink your email strategy. You can't game the system though. Because the system is based on people's consumption. And so if they're not consuming, then that's, it's game over.

Right? And that's your fault as the writer. It's not Gmail's fault, it's not iCloud's fault, because their systems are based on consumption and interaction. Just the same way that search engine optimization is really like search engine consumption. It's based on people's interaction, time on page, scroll, blah, blah, blah, right?

There's a little bit of legacy SEO still in there. But it's all just based on stuff from Google Analytics. We don't get access to it, so we don't really know. So the only thing that we can do is monitor our rights. are people engaging with this content in the ways that we can track?

Clicks, revenue, which is really the most important metric that we all forget about as, marketers. opens and clicks, paint a little bit of the picture, but really the only thing that actually matters at the end of the day is if there's money going into the bank account.

And your email, like you could send 10, 000 emails and get a 50 percent open rate and a bunch of clicks, but it doesn't make any money. Was it really that effective?

[00:30:32] Zack Katz: So here's the thing with that.

[00:30:33] Amber Hinds: in your email.

[00:30:34] Zack Katz: a few things about that. One, I ran some numbers from our newsletter only campaigns for, 2023, 2022.

Our email, dropped a lot from that time for Black Friday. 2022, we brought in about 20, 000 directly from the newsletter, mailing list. 2023, it dropped to about 10, 000, but I do feel like there's a, top of mind aspect of it that even if you don't. Convert directly from an email.

An email being in somebody's inbox can help remind people. So I think it emails not only a direct marketing, it's also a branding exercise where you're top of mind if somebody even sees your email. So I do think that there's a little bit of that.

[00:31:18] Adrian Tobey: Absolutely. But the top of mind strategy really only works if you've done the training and you've done the sending good email that people consume, right?

Because if it's being ignored, then it's not really Particularly effective then, or if it's going into the spam folder, if it's just getting lost in the promotions folder, along with all the other junk.

[00:31:36] Zack Katz: Yeah. Adrienne, we are getting close to time. It's now time for our best advice, part of the show, where we ask, what is your best advice to product owners who are trying to figure out how to make email marketing not suck?

[00:31:51] Amber Hinds: Do we feel like we should at least touch for a second on Black Friday, given the timing? Like I, and maybe you have other best advice, Adrienne, but I'm curious what your best advice Black Friday, because I think a lot of people are probably working on those emails right now. Do you have a recommended number of emails or like any other things?

And so maybe you could do that first and then do broader best advice, but I really would like to hear your thoughts on that.

[00:32:19] Adrian Tobey: And Black Friday, I have, over the last six years, invested a lot of hours in developing, Black Friday emails, strategies, and sequences, and whatnot. so what everybody's doing right now, we talked about this a little bit at the beginning, is everybody's warming up their MailChimp accounts or whatever.

And they're going in and they're designing, okay, 50 percent off, 75 percent off, whatever. And they're all going to send that on November 25th or whatever it is. they're just going to bombard people's inboxes for the next however many weeks.

And that's just what they're going to do. And You as a business owner who has your own list that may or may not be particularly warmed up or you may have not been particularly frequent in your communication are going to do the same thing and you're just going to shoot enough shit at the wall in a shotgun approach and see what sticks, right?

And that's where we are at in the evolution of email marketing during Black Friday I think we've reached to a point. And buyer habits where people know what they're looking for already. They know what they want.

I think we're beyond the point where people are just buying stuff for the sake that it's on sale. Maybe not, but that's my take on it having seen sort of the progression of our own sales and other WordPress product people's sales. People know what they're looking for and they're just like waiting now.

For the deal to come through and have their list of things that they want to acquire. And so you could spend hours and hours, crafting a beautiful sequence to send to people's inbox about your Black Friday deal. Or you could just send an email to the people that are already on lists that maybe haven't bought and say, Hey, listen, you've been on our list for a while.

You may or may not want our product, but here's a discount if you do, because just because it's Black Friday and you can buy it on this day or for this amount of time. And I think that would have the same level of effectiveness as planning out two weeks of building up some sort of deal.

It's hey, our deal is going live in, three days I really don't think that's at the same level of effectiveness as it was previously. Your mileage may vary. But given that you have been active For your subscribers, one email every couple of weeks, right? They know who you are and you send them a discount or you send them a deal or whatever sort of value that you want to provide during Black Friday, that's going to have a higher level of effectiveness unless you're just emailing people for the first time, I don't really think there's any saving you.

To be honest, because it's been too long, and it's been, it's not warm, and you're just not relevant in people's minds, and you're just going to be contributing to the noise. If you don't want to contribute to the noise, right? And you want to do something, the different tact that you could take during Black Friday is not to send offers.

It would be to actually do the opposite. It would be to send value, right? It'd be reinitiating that two way relationship between your brand's personality or yourself and your subscribers. And that might have a little bit of a higher impact because while everybody else is sending deals, you're sending value and that might make you stand out.

So I think that might be worth thinking about.

[00:35:38] Zack Katz: Those are great. How about you, Amber?

[00:35:41] Amber Hinds: Oh, . You want me to go first? Okay. I have found that we do better just talking Black Friday. We do the Monday before through the end of the month

we usually send one on the Monday when it starts. we don't send any more emails during Thanksgiving and Black Friday because I know everyone's getting a bunch and also most of our buyers, because we're B2B, are not in the office, especially our enterprise level people, and I assume they just get in the office on Monday.

And they find all the sales emails and they just select them all and hit delete. They don't even open them. So we then send more on Cyber Monday and like towards the end of the day. And then we send two days left.

One day left, 12 hours left, and we have gotten sales off of all of those, and that has worked really well for us, and we still get sales during Black Friday, but I don't feel like on literal Thanksgiving holiday, people need to get an email from me. If there's someone who's going to buy it during Thanksgiving holiday, instead of eating turkey or whatever with their family and friends, then they're going to do it without an email from me is what I have found.

So I mean that, that's my, I agree with Adrian. Like maybe you have to rethink the number of emails or like when you send them. But I do feel like the time limit in the beginning, I wasn't doing as many and those there's so much time left, so much time left. The sense of urgency really gets people because we don't do sales all the time.

We do sometimes give discount codes for, when we sponsor an event, but even that we're not doing as much of anymore. Like we didn't do as many of those this year. So I feel like that's helpful because it is real urgency and not people aren't reading it as fake urgency. So I think that's my Black Friday best advice.

[00:37:43] Zack Katz: Wow. I'll be the one person here who thinks you should send emails on Black Friday. So we also don't send any emails, during Thanksgiving because I think, it's not all our customers are from the United States, but I do think it's a, some things should remain sacred. And I think that, the agnostic holiday of Thanksgiving, where we give thanks.

should not be one of marketing. And I do think that's really nice to honor that. So we don't send any on Thursday. Black Friday emails are big for us. We send one in the morning, one in the evening. And then the same for Cyber Monday. We might even send three on Cyber Monday. Because the email is more like a live feed at that point, people's inboxes.

So you got to stay, on top of that feed, but the Cyber Monday evening one is one of our best performing, emails. So I do recommend mixing up your times, allowing yourself to send multiple emails per day, split testing subject lines. And the calls to action and seeing what types of emails are driving your customer base the most, and then refining your future emails in the same campaign.

So Cyber Monday 2024, should be tweaked based on how your earlier emails are going throughout the Black Friday, Cyber Monday sale. If you're not getting good results from your earlier emails that you've scheduled with a certain call to action, Change that in your emails moving forward.

That's one of the nice things about having a couple weeks long campaign is that you can adjust it live as you go. So those are some of my tips for Black Friday, Cyber Monday. we send out an email ahead of time, ahead of the sale, to people who subscribe to our newsletter. And it's included in our newsletter for a couple weeks in advance that says, Hey, we're going to be sending a lot of emails.

If you don't want our Black Friday emails, click this link so that people can, then we tag them in our CRM that says, don't send these people emails for Black Friday. And that makes it so that they can opt out in advance without unsubscribing, which saves us a lot of email churn. Because we don't want to lose people from our newsletter list who are not interested in the sale.

Also, we don't send emails to people who already have our highest package and are already, up to date because we don't have anything to upsell them. So I think thinking about your email list ahead of time and seeing if you can sculpt your list a little bit. Before you start your campaigns can really help shape it in a way that only the people who want to see it can see it.

[00:40:23] Amber Hinds: Yeah, I feel like we could probably have a follow up with Adrian at some point where we just talk about segmentation. Because that is probably a whole topic. It's an art.

[00:40:32] Zack Katz: Art of Segmentation, because it is truly, something that I think people should get awards for in like best segments.

So now for not Black Friday best advice for emails and email marketing. Toby, what do you got? What's, er, Adrian I just saw. Both

[00:40:51] Adrian Tobey: are equally valid. Best advice that I got.

[00:40:54] Amber Hinds: This is like this, the elevator pitch best advice.

[00:40:57] Adrian Tobey: Yeah. Focus on the right metrics for your business.

When it comes to email marketing, I mentioned this earlier, there's lots of chasing opens and clicks, and that certainly has its place. But chasing opens and clicks leads to writing content that chases opens and clicks, or a specific format that chases opens and clicks, and then you get confirmation bias.

Where that opens clicks don't necessarily always translate into actual sort of revenue performance. And so you should always be tracking, okay how is my email strategy impacting growth either for users, for revenue, whatever, because if you get into the confirmation bias where your only success metric is opens and clicks.

I see this a lot with our customers. It's just, they, all of a sudden it's okay why, Is this not having a movement? What actually matters, right? And so if you can track that somehow, or set up tracking, I know with Groundhog, we have like integrations directly with EDD and WooCommerce to track sort of the journey from email to, to purchase, even if it's not direct.

So if you, if your CRM can enable that somehow, then that's what I would be focusing on, like I said earlier, you can send 10, 000 emails and get 50 percent open, or you can send highly targeted. Really personalized email to five people, right? Get five opens and get five purchases. And if you could spend like the most time doing one thing, what would you prefer to do?

Take less time, less money, highly personalized, lots of revenue, And there's places for both, right? It's just don't put all your eggs in the scattergun approach.

[00:42:41] Amber Hinds: What's your best advice, Zack?

[00:42:43] Zack Katz: Oh, for my best advice. All right. It's an oldie but a goodie.

I've said it before and I'll say it again. Split test. I love split testing subject lines. It's fascinating to me. I, appreciate the human nature, tweaking that goes on. you don't always know what is going to drive people to open your subject line.

Your emails and tweaking your subject lines will inform you as to what your customers are looking for in the email. And if that's a nicely aligned thing where your subject line and your email content works, then you will find, that tweaking your subject line will result in more revenue. USP for email per email sent, which always blows my mind that the same email content can have such different results based on subject line.

It doesn't make sense, but it's the subject line, like Adrienne's talked about so much today is like priming your customers to know what they're getting into by opening and reading your email. And if that's nicely aligned, that results in more revenue. So split test. How about you, Amber?

[00:43:47] Amber Hinds: I think it's really think about how you can provide value and connect your emails with the value you provide outside of email, right? They should be partners in your effort. as I mentioned before, this thinking about value should be over the course of a year or a quarter or whatever it might be if you go a quarter at a time, but like thinking about the story that you're telling with your email communication.

Not just sending it when you're having a sale.

[00:44:20] Zack Katz: That's great. Adrian, thank you so much for joining us. Where can people find you online?

[00:44:26] Adrian Tobey: So you can find us at groundhog. io. That's groundhog with two G's dot IO, or you can find me on Twitter. Adrian Tobey.

[00:44:33] Zack Katz: be the pet in. It's GrandHog with three G's, two G's at the end.

ChadGPT Yeah. How many R's does Strawberry have? Forty five. GrandHog, such a great resource. Check out GrandHog. The website, your website has so much good information for Google who are just getting started. with their WordPress product journey.

So check out Groundhog with two G's at the end. com. I apologize, Adrienne.

[00:44:57] Amber Hinds: io.

[00:44:58] Zack Katz: And tune in next week where we will be hosting a conversation with all our co hosts about navigating the plugin directory in light of some of the most recent WordPress drama. There's been a lot going on in the WordPress space and you will not want to miss this episode because we have opinions.

[00:45:14] Amber Hinds: Yep. And special thanks to Postonis for being our green room. If you're enjoying these shows, please do us a favor, hit that and subscribe buttons, share this episode with your friends, post it in your newsletters, We want to get shared. We appreciate it.

And then most of all, come back next week and we'll see you then. Bye.