Email is an essential part of just about any CMO's toolkit, but with so much competition out there, it can be tough to make yourself heard.

That's why we're back with Aidan Casey, CMO of Paintru, who joined us for another episode of CMO Diaries to discuss her approach that's practically doubled her email conversion rates. While it was originally an episode of our podcast, you can find a write-up of everything we discussed below.

CMO Diaries | Boosting email conversion rates | Aidan Casey
In a world where the average person receives over 100 emails a day, it takes work to stand out so you get the conversion rates you need. That’s why Aidan Casey, CMO of Paintru, is back with us to share her approach that’s doubled open and click-through rates.

Why is email marketing still so important?

Today's gonna be on a subject that is very important to many CMOs, because we're talking about email marketing, particularly how to improve that open conversion rates.

But before we get into it, let's maybe break down why it is important to have a good email marketing system in place in this day and age. With all the social media and other marketing channels we have today, email marketing is like the old workhorse that just keeps delivering results, particularly for B2B, but also in D2C, which is your perspective, Aidan.

Yeah, definitely. I'll start off by saying, I completely shifted my mindset around email marketing over the past year and a half. I used to hate email marketing. I used to push it off to anyone on my team who was willing to pick it up.

I decided that when I started with Paintru, I was going to really learn how to leverage it. Data shows that email has one of the highest conversion rates of any platform, especially in the E-Commerce space. I realized that for Paintru, especially our product being kind of a novel solution, direct to consumer custom artwork, there's a lot of education that needs to happen.

Our buying cycle is very long. Email is a great channel to nurture leads, answer any questions that they have, and also give them project inspiration. We've talked about this quite a bit in previous episodes, but our content strategy for Paintru is really “inspiration.”

People don't know what they can have until you share different projects. So for us, it's inspiring our customers and potential customers with different painting ideas. Whether that’s having a  travel photo painted, or a wonderful Valentine's Day gift for your significant other, people just don't know what they can have painted until you tell them and open that communication.

All of those factors come into play with our email strategy. And it's just such an effective channel. Because we have such a long buying cycle, we have to have all those brand touchpoints and education to drive home what we can do to keep people inspired.

It's one of the channels where people are most willing to have these lengthy, long-winded conversations. They’re able to drop back in and out in a way you can't really do that over social media, and you can't really do that over other channels. Maybe it's because, for better or worse, people accept marketing on email more than they do other channels.

It feels less intrusive, because it's your email and we've been getting email marketing for a long time now. We're okay with getting personalized targeted emails, but if we started getting personalized, targeted messages through other channels, that's when people start to become reluctant.

Yeah, people are used to receiving emails. It's also a challenge, though. How do you cut through the clutter? I use Gmail for my personal email, but I have loads of promotions and updates that come through. Every time I'm creating an email, I look at it through the lens of, “How am I going to enrich the recipient's day?”

We're a fine art company. We have all these beautiful paintings and projects we can share. I like to think that our emails are really fun and beautiful to look at. I'm always thinking, “Okay, how do I enrich the user's day by sending this email?

Also, how do we get to the intent of the email? So, a lot of our emails are just like project inspiration. But with some emails, if we have a sale going on, or if we have a certain type of promotion or a new product, we need to get that point across quickly.

How do I make sure that the user knows what the email is? We need to get that point across quickly because most people skim emails these days, even if they do open it.

Don’t just create content - do something with it
Randy Frisch, CMO of Uberflip, joined us to outline his vision for content marketing: rather than just churning out content, we need to be developing curated experiences.

Step 1: get people to open your emails

As you said, people get so many emails. A lot of people have their work emails being forwarded to their personal emails as well. You've got all that mess to get through as well. The main challenge is just to get people to open their emails.

Yeah, and that's all in the subject line. The subject line is this tiny bit of text, but it carries so much weight in your email program. If you have a poor subject line, no one's going to open the email. My team laughs at me sometimes because I spend a lot of time on my subject lines. But we have a pretty good email open rate. So, it's worthwhile.

I try to be really fun and conversational, too, I think. When you’re building a brand, it's so important to be consistent with your voice and the way you talk to your customers across all channels.

I do really try to keep our email pretty upbeat and conversational. I like to have fun with them. At the end of the day, we're inspiring people to be creative. We have such a creative product. I sent an email last Thursday, and it was kind of a roundup of different customer reviews from orders that were placed around the holidays.

Those subject lines I used were covered in stars. It's one of those opportunities where it's playful, but it's still on-brand for us as an art company. I love email marketing now. It did take me a while, but once I dug into it, I was able to really start nerding out and analyzing things.

Getting inspiration from other email programs I have, it's kind of turned into one of my favorite channels. And as we grow as a company, email is probably one of the first things that I should delegate to someone else, because it's not really something that the CMO can still be running.

But I will admit it'll be a little hard for me to get that off my plate just because I enjoy doing it. I enjoy writing them. I love hearing the feedback from customers where they respond and comment and give feedback on the emails. It's very satisfying. When the sales come through from the emails, that is the ultimate goal.

When we're talking about the open rate process, let's start with sending the emails because that's step one of getting onto someone's radar. Do you have certain times when it’s best to send them? How important are the times that you send these types of emails?

Yeah, I've found the best open rates to be around 7:45 to 8:45am. It’s when people are doing that morning sweep of their emails. I have pretty good open rates if I send around noon as well, which I would assume is when people typically will go back and check their personal email around lunchtime.

I will send an email Sunday morning, sometimes around like 10 or 11, which have fairly good open rates as well. I typically try to avoid afternoon or evening just because the likelihood of that email getting buried by other emails the next morning is pretty high. That's what I’ve found.

It's been a while since I was working in B2B, but I feel like there's been some studies that B2B email in the afternoon to evening is pretty effective. For me, I tend to do it in the morning and if I'm working on an email and putting some final touches on it and need to send it a little bit later in the morning, I don't think it's really the biggest deal.

But I'm kind of fortunate because I am in the UK, but my customer base is in the US, so I can have everything scheduled to go in advance. I have this whole morning where I can fine-tune the emails before I even schedule it.

And then the next step once it's in the inbox is: what is the subject line like? How attractive is it? You said that you like to use a conversational tone, how do you do this? Do you use emojis?

I use emojis a lot. Another component of the open rate is the preview text, which I don’t think some brands leverage to the extent that they could. A lot of people skim emails, and you see that subject line in preview text, especially with how Gmail formats things.

The preview text is another amazing spot where you can really tell people what the meat of that email is going to be. Typically, if we're having a promotion going on, I'll have a catchy, fun additional line that's relevant to the promotion.

I use that preview text to immediately ensure that people know that there's a 15% off code inside. And people do see that right away as well. I do use a lot of emojis, but I won’t use someone’s name unless I’m sending a plain text version.

I leverage a mix of marketing, branded emails, and also some direct outreach, especially from our three founders. In those ones, I will use the name, but those ones I'm very careful about. We have about a 40% open rate on plain text emails.

But I think it's really important not to abuse that. Because if we start sending plain text emails every week, the uniqueness factor will be lost. For those, I will address by first name, but that's typically a very segmented group of customers that we're sending to.

I actually have an instance where I use a first name when we are emailing a very niche VIP group, or someone who's ordered within the last five days or something like that. That segment is super small, and we are speaking to them on a more personal level.

People are smart, and they know that a marketing email is being broadcasted to everyone. So I feel like it's a little disingenuous to have the first name when I'm just sending an email to everyone about some awesome paintings. In these cases, people know that these emails are being sent to everyone.

The double-edged sword of personalization

The novelty of a brand knowing your name has kind of worn off now, hasn’t it?

Exactly. it's like that's been around for ages all of that. But when it's a direct email, like, for example, a thank you for purchasing something from the founder, it’s natural to have a first name in there. That would be a direct, plain text email.

Yeah, so with automated emails, where it's responding to your actions as a customer that you've taken on the site, you get an email addressing you by name in order to make it personalized. That makes sense.

Our automated email sequences are so important. We spent a lot of time and energy dialing those last year. We have a welcome series for someone who has already subscribed and has now just purchased. We have a new subscriber welcome message.

I think we have 11 emails in that series right now. Because, with our buying cycles, it's such a long decision-making process and there's so much information that we need to share. So, we have about a three to five day cadence in which those ones will go out.

We have a drifting customer re-engagement sequence. We have a lost customer reengagement sequence. We have a new lead sequence. Anyone who's live chatted with us and had a conversation with our concierge team will be marked as a lead, so they get a pretty personal sequence as well.

Those ones are so important, and we've just found those have a really big impact on our business. And we get a lot of purchases from the welcome series, which is great. We also have a welcome series on our SMS as well. They are different, yet some of the content is similar. We just want to answer everyone's questions so that they feel confident in purchasing from us and they also feel inspired.

Make opening the emails worth their while

Fantastic. So, they've got the emails open, what do your emails look like? What is the format? Do you use images?

Yes, we do. I know there's a slight risk in that. Some email providers will block the images at first. But it's a risk that I'm willing to take just because our product is so visual. Typically, if you're not signed up to email us already, I have like a big full image of a painting with our logo and a topic.

And then we have a big headline. I actually do have a drag and drop editor. I have text within the email, which has higher deliverability than having text and an image. I'm actually working on getting some new HTML, editable templates now. So, that text will come through, and they’re very image-heavy. Typically, whether it's a review, or whether it's a sale, a new product, gift ideas, or different painting ideas, it all really goes back to what the paintings are. Even in our review emails, I'll typically include the painting that someone is leaving the review about.

So, it’s very image-heavy. Again, it also goes back to my thinking around the intent and the purpose of our email program. I want something beautiful that people want to read. And if people aren't interested in seeing art, then they're welcome to unsubscribe, and that actually just strengthens our email content, or our email list moving forward.

Yeah, if they're not interested in seeing art, then they're probably not going to be your customers.

I consider it a bit like a list cleaning. We do that on SMS and email. We're very upfront in our welcome series. And those emails are beautiful, there's a lot of art in them. And if someone's not interested, then no one's gonna stop them from unsubscribing.

Unsubscribes are just natural, really. I don't see that as a bad thing. But if we have a huge unsubscribe percentage on a certain type of content, we have to take that into account. That's not content that our audience is interested in.

The danger is that you could end up getting flagged as spam, especially if too many people are ignoring your emails, or flagging the emails. Your entire domain name could be flagged as spam whenever you send stuff out. Having that process where you get rid of the deadwood is an important part of managing a good email marketing system.

Exactly. One of our big goals is to increase our subscriber list, because we see a pretty good conversion rate in that community that we build. I like to think of it as a community. We're having conversations with those customers, or potential customers, and we have about a 50% engagement rate.

I actually haven't looked at that against a benchmark, but I consider 50% to be pretty good. That's people opening almost all emails. It’s developing a relationship with them as a customer. Especially if they're subscribed to us on SMS as well, that just strengthens it, because it's what people typically purchase after seeing your brand 11 times.

There could be updated data on this since I last looked, but email is just another one of those touch points. It just keeps us top of mind.

When it comes to content as well, emails are really good environment for testing. It's a very effective for split A/B testing. How much do you dive into that when it comes to the types of images you use, and the types of content?

Yeah, I'm gonna be completely honest, I probably don't A/B test as much as I should. I do A/B test subject lines. It's a little tough sometimes because you have to make sure that you're being diligent about collecting the feedback that you're getting from those A/B tests. For example, does humor work better, or does urgency work better?

And yeah, sometimes it's pretty time-consuming to be testing and then taking all that feedback and moving forward. So, I guess I've learned which subject lines work better for us by quantitatively looking at those numbers from the tests. I actually don't really test the content. Because, as a CMO of a startup, there’s a lot of hats I have to wear.

Yeah, well, that's something you can do when you do get to the position where you can have someone else taking over. As a CMO in a startup, you're hiring people to do certain jobs better than you, and you're able to focus on other things.

Exactly. And I am definitely data-driven. When we get to that point, I'm just going to want to see the numbers. Data over ego is something that I always try to come back to, even if I personally think that something is better. Let's look at the data, and what does the data say? Because that , at the end of the day, is how you improve your program.

Getting those click-throughs

Definitely. Speaking of data, and knowing where to place things on the email page, have you ever played around with where you place your CTA and stuff like that? When it comes to getting those conversion rates, because that's the ultimate goal, it's not just about getting people to read the email, you want them to do something with it at the end.

I try to make sure that I have a CTA at least above the fold on a desktop, which is probably one scroll down on mobile. But with a product highlight image, I don't link those because a lot of times people like to zoom in on them and check out the painting.

But with other images, I always make sure there's a link there, because a lot of people just click the image expecting that to take them to the site. I'm careful about that. I mean, if it's a long email, there are at least three CTAs. I also make sure it's really relevant for the segment. I segment my emails. I always segment purchasers versus nonpurchasers. And a lot of times I'll segment further into VIP customers and multiple purchases, abandoned carts, etc. I make sure that the CTA is relevant. For a nonpurchaser, it's something like “create your masterpiece,” or “get started on your first project, upload your photo and match with an artist.”

For repeat customers, I'm typically thinking something along the lines of “start your next masterpiece,” or “ get inspired for your next piece of artwork.” It’s usually something like that. I do want to make sure that we're speaking to our customers like they already are a customer because they are and I think that's why email segmentation is so important and effective.

The medium is the messages
Aidan Casey, CMO of Paintru, joined us on an episode of CMO Diaries to share the success she’s had with SMS marketing, along with advice for other CMOs in how to utilize it, and a look to the possibilities the channel could have in the future.

Segmenting for success

Let’s talk a bit more into segmentation. The studies on the effectiveness of segmented email lists are huge. The amount of impact you can have in terms of just quite simple segmentation can be really powerful. So, did you already have these segments in place when you were starting out?

The email automations are very complex. I will never say that it's simple. There are a lot of great email platforms out there that can help but it takes time, and it definitely pays off. So, we created different segments: Drifting customers, lost customers, VIP loyalists, big spenders, all of those segments.

Also, of course, we have a lot of different purchase timing segments. S, we have: purchased within the last three days, purchased within the last week, purchased within the last three weeks, purchased within the last two months, etc. Sometimes it can take six to eight weeks before the painting is finished and delivered just depending on the revisions.

I'm not going to hit someone with a promotion he just ordered a week ago. That's not a good customer experience. So, I'm really careful about that. A lot of times if I'm emailing and I'm creating my customer email segment, I will actually exclude people who purchased one time only within the last two months because I don't really want to talk to them yet.

Also, we use HubSpot. There's a tool on there to only send to your engaged contacts. I’m not exactly sure how they calculate it. But I think it's engaged with X percent of your previous emails. Like I said, our engagement rate is about 50% of our non-customers.

So, with some emails, I will uncheck that box. I want everyone together. I want to give those unengaged customers another opportunity to engage with us. And then other emails, where it’s just project inspiration or just sharing something beautiful, I'll only send them to our engaged customer because that's a way to boost our email credibility.

If you're not engaged, you probably only care about critical information and promotions. So, I send those to those people and I'll send reviews to everyone as well to give those unengaged contacts and other opportunities to check out our stuff.

Measuring your performance

So, what are some of the metrics that you're focused on when it comes to deciding what makes a good email marketing system? We've talked about open rates and conversion rates. Is there anything else that you really think is important when it comes to signing?

I mean, the click-through rate is definitely a big one. If I'm sharing a new blog, or trying to inspire non-customers to upload a photo and get started, click-through rate is important.

And I always look at that. If I have a huge unsubscribe rate on certain emails, I have to step back and assess what type of content was included in the email? Clearly, a large segment of people were not interested in this. So, that needs to be accounted for moving forward.

Yeah, you could learn just as much from those failures, right?

I think sometimes you learn more from failures, yes.

Without being able to see where people are unsubscribing, you're not seeing that different perspective on what's effective.

Yeah, exactly. Another one that I look at quite often is our welcome series. I mentioned that we have 11 emails in that series currently. I look at HubSpot, where you can set the goal that basically if someone purchases, that goal is achieved. They no longer need to be in this welcome series.

I look at the percent goal met in each of those emails. For example, I threw in an email a couple months ago that I thought was great. But there's been no purchases off that email. But there have been purchases on all the other emails.

So, again, that’s data over ego. I’m accepting that this email is not as effective as other ones. I need to consider replacing that with something else, or removing it and then slotting another email. Something I do a lot is, if I create an email that people love, that has great open rates and conversion rates, I'll actually just throw that into our welcome series.

I repurpose emails that way, because most of our emails that I mentioned are about product education and inspiration. Almost all emails we send would be suitable to slot in that welcome series, if it's something that will help people convert or understand our product more.

The process keeps evolving

Awesome. So, what's next with your email system? Do you have plans for where you want to develop it in the future?

I'm refreshing our templates right now, as I mentioned. I'm going to work on getting a full HTML, instead of a drag and drop. As we evolve as a brand, I think our emails are great as is, but we can make them better. I had a designer design a few email templates for me, so that hopefully should improve some of the deliverability at times.

I’m planning on revisiting a lot of our automations so that our drifting customers re-engage, and our lost customers re-engage. Those ones have been up and running for several months now. We need to revisit those. Also, I'll probably assess whether we can segment further? Are there any other segments that we might be neglecting that we could create a sequence for?

As far as email cadence goes, we'll probably keep with that. I think a big one is revisiting a lot of those segments. With the welcome series we constantly revisit, so I'm pretty comfortable with that. But with the drifting customer re-engage, I definitely need to revisit that one, because that's such a critical segment. It’s about capturing people and converting them from customers into loyalists, encouraging more projects and soliciting feedback, etc.

Further resources

Awesome. Let's talk about what resources are out there for people to really learn how to get good emails. You said you use HubSpot. They're always a great resource for this kind of thing. But is there anything else that you found really helpful in developing this system?

I actually will recommend a podcast, E-Commerce Marketing School. I’ve found this podcast incredibly helpful. They're like bite sized nuggets, from four to 25 minutes an episode. I listened to that a lot. They talk about specific brands, even if it's something completely irrelevant to our business.

They're tidbits that are really helpful. So, I listened to that a lot. There are also a lot of good  books you can read around the subject. I also think it’s just about just getting in the head of your customer. That can be really helpful. I look at my email inbox with my marketing hat on every single day.

Taking a step back and realizing and recognizing what emails are effective for you can be really helpful. Every single time you open an email and you are engaging with the content or you like it, or it drives an action, you should be taking note of those little tactics that they're using.

I get a lot of inspiration from other brands. Again, even if they're not relevant to my business, there's a wealth of knowledge just sitting in your promotions and your updates tab.

Golden rules of email marketing

Definitely. We can take that last point as a sort of like the golden rule. When it comes to email marketers, you should get into the mind of your customers. You want the email that you're sending to be something that they're looking to, that brightens up their day. Any other golden rules you want to throw out there?

Just one more thing, check your links. Taking an extra 5 to 10 minutes to quality check your email will save you so much heartache and stress. I think that for people who are new in email marketing, it's scary when you create this email on Sunday and you’re worried about whether you should schedule it. As you get more comfortable with it, you get better at it.

Like I mentioned, I didn't really enjoy email marketing. It was definitely a challenge for me previously. Now, like I said, I love it. That being said, you do get faster, but take an extra 5-10 minutes, quality check your email, check your links, etc.

Sometimes, if there's a little typo in there, your customers probably won't notice and they will forgive you. But I had one email that went out that had the wrong link in it, and that was very disappointing for me, because I like to consider myself a good quality checker. I guess that's another good tip. Also, get feedback from your team to make sure that your entire team is signed up for your emails.

They should be looking at them every single time. I welcome feedback all the time for my team members. If they don't love an email, or if they miss it, maybe they don't think the subject lines are great. Or maybe they think that there's like a better way it could have been presented. I think that open feedback is great.

I also encourage all my friends to sign up for our emails too. Again, that is because we're D2C. Anyone in my network could be a potential customer. So, I'm forcing all my friends to sign up for our emails and let us know what you think. I have probably 10-12  friends in marketing that I have signed up for a welcome flow. I encourage them to give me feedback.

Do you still have questions after you've gone through this four week email series? Are you confused about anything? Let me know! This network can give you a lot of feedback, especially if you're D2C. And if you're B2B, I think that leaning on your teammates and asking for feedback can really help.

Definitely. It's good you mentioned B2B at the end, because, as we said at the top of the article, B2B and email marketing are intrinsically linked. You can't have B2B marketing without email marketing. Even though we're talking from a D2C perspective, a lot of this stuff is very relevant to B2B.

Yeah, and going back to my experience in B2B, I worked for a health tech platform for years, and I kind of offloaded the email marketing to another team member. But email is such a great channel for education. So, I mentioned education and educating our potential customers, but in a B2B email sequence as well. If you work on a SaaS platform, it’s a great way to keep your brand top of mind.

If they're using your technology and using it correctly, and are aware of any new features or anything like that, that’s going to keep them engaged. As an example, I use Grammarly, which I love because it's a great platform. They send about two emails a week, with some really great language tips.

If there's a platform improvement or something new, they send out an email about it and make sure that I have Grammarly installed everywhere. I'm also aware of what's new, because people don't know what's new unless you tell them, and email is an effective way to do that.

Do you have questions on how to improve your email conversion rates? Head to the CMO Alliance Community Slack channel to join the conversation and get advice from CMOs around the world.