Email marketing remains one of the most powerful tools for e-commerce store owners but what really works for WooCommerce merchants, and where are most falling short? In this episode of Do the Woo, we take a deep dive into the strategies, tools, and future trends shaping email success in online retail.
Your hosts, Katie Keith and James Kemp, are joined by special guest Simon Harper, a seasoned expert in WooCommerce, email marketing, and deliverability. Together, they discuss the most effective email flows for stores, how to nurture customer relationships, and the role AI is beginning to play in personalizing and optimizing campaigns. Whether you’re just starting out or looking to take your store’s marketing to the next level, this episode delivers essential insights and practical advice to help you get the most from your email list.
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Takeaways
- Email marketing is highly effective for WooCommerce stores: Simon Harper highlights the uniquely personal relationship-building power of email, emphasizing its status as an “owned” channel with high ROI potential, control, and data-gathering capabilities beyond other digital marketing methods 02:55.
- Personalization and relationship-building are key: Success in email marketing hinges not on list size but on the relevance and personalization of content; the trend is moving toward smaller, more focused lists and meaningful customer engagement 06:49.
- Welcome and post-purchase flows offer the highest impact: Simon Harper recommends focusing on well-crafted onboarding (welcome sequences) and post-purchase email flows as the biggest opportunities for WooCommerce merchants, helping guide customers and reinforce relationships 47:16.
- Consistent communication is critical: Many merchants neglect regular email outreach, relying solely on transactional messages. Sending at least a weekly email keeps brands relevant in customers’ inboxes and boosts deliverability and engagement 24:24.
- Preference centers show respect and reduce annoyance: To avoid irritating customers, stores should offer email preference centers, allowing people to pause, opt out of specific campaigns (like Black Friday), or tailor their email frequency, improving brand perception and reducing unsubscribes 26:27.
- WooCommerce merchants underutilize advanced email tactics: Compared to other platforms like Shopify, WooCommerce users tend to keep email marketing basic, often missing out on flows, segmentation, and post-purchase strategies that can boost growth 11:18.
- Legal compliance is vital in abandoned cart emails: When sending abandoned cart or checkout emails, it’s crucial to respect informed consent laws (like GDPR), limiting messaging to the products left in the cart and offering opt-outs at checkout 30:01.
- Pruning and segmenting lists drives better results and lower costs: Regularly cleaning email lists by removing unengaged subscribers not only cuts service costs but increases engagement and ROI—a smaller, active list beats a bloated, passive one 32:30.
- AI is most valuable for data analysis and segmentation—not just content generation: Simon Harper points out that current AI tools excel at analyzing customer data and identifying marketing opportunities, whereas using AI for email writing or template generation still requires human oversight for tone, accuracy, and quality 37:10.
- Overcomplicating automations often backfires: Simple, focused flows—like welcome series, abandoned cart, post-purchase, and review requests—are manageable and deliver the best results, while overly complex automations can become difficult to maintain 21:33.
- AI-generated, impersonal, mass newsletters and cold emails are a poor use of the technology: Creating soulless, generic newsletters or relying heavily on AI for cold outreach does not foster real engagement and risks damaging the sender’s reputation 44:53.
- Email marketing is a long-term investment: Results compound over time through regular, thoughtful communication, focusing on building trust and relationships rather than trying to reap immediate conversions from one-off campaigns 49:00.
Questions Asked in this Episode
Q: Why is email marketing considered one of the most effective channels for WooCommerce stores?
A: According to Simon Harper, email marketing is highly effective because it enables merchants to build ongoing, personalized relationships with customers—something that’s hard to match via other channels. The control over the audience and data allows for tailored communication throughout the entire customer journey, leading to greater engagement and higher ROI than most other marketing methods 02:55.
Q: How will Google’s AI-powered inbox features change email marketing?
A: Simon Harper discussed how Google’s forthcoming AI inbox will create hyper-personalized experiences where each user’s inbox will be uniquely organized, making it critical for marketers to focus on genuinely relevant and useful communication. While the full impact remains to be seen, staying relevant and delivering value will become even more essential to avoid being filtered out by intelligent inboxes 04:12.
Q: What are some simple but essential email marketing flows every WooCommerce store should have?
A: At a minimum, stores should implement a welcome email sequence (ideally around three emails), abandoned cart and abandoned checkout flows, and post-purchase follow-ups such as review requests and education about the product. Simon Harper emphasized that while complexity can add value, consistency and simplicity in these key areas already make a significant impact 21:31.
Q: Why do WooCommerce stores often fall short compared to SaaS platforms like Shopify in email marketing?
A: Simon Harper and Katie Key noted that WooCommerce’s flexibility can overwhelm merchants, leading many to stick with default features and neglect deeper optimization. Unlike Shopify, which strongly nudges new users toward specific email marketing tools and built-in flows, WooCommerce users may lack the education, prompts, or resources to go beyond basic transactional emails 14:44.
Q: What can be done to avoid annoying customers while still sending enough marketing emails for good results?
A: The panel suggested offering customers control through robust preference centers, allowing them to pause, limit, or opt out of certain types of emails like Black Friday promotions. Respecting customer inboxes and providing options for communication frequency helps protect relationships and reduce unsubscribes while still maintaining contact 26:14.
Q: How can AI be used effectively and safely in email marketing for eCommerce?
A: AI is most helpful for analyzing customer data, identifying segments, and helping draft content in the merchant’s voice if properly trained. However, Simon Harper cautioned against relying on full automation without human oversight, as factual and tone errors are common; AI should be viewed as a tool for efficiency and insight, not as a stand-alone solution 37:10.
Q: What’s more important: building a large email list or having a more targeted, engaged audience?
A: The episode highlighted a shift in best practices from prioritizing list size to focusing on smaller, more engaged lists. A highly targeted audience results in better deliverability, higher conversions, more meaningful relationships, and cost savings on email platforms, as discussed during the conversation on re-engagement campaigns and list pruning 32:30.
Q: If I only have limited time or resources, which email marketing areas should I focus on first for my WooCommerce store?
A: Simon Harper recommended prioritizing a strong welcome/onboarding sequence for new subscribers and an effective post-purchase flow that includes product education and review requests. These touchpoints offer the greatest impact on building trust and driving sales, providing a solid foundation before tackling more frequent newsletters or advanced automation 47:14.
Mentioned Links and Resources
LoopWP – An awesome newsletter about WordPress and WooCommerce
🔗 https://newsletter.loopwp.com/
Add To Cart Blog – WooCommerce’s educational blog series with practical advice on optimizing online stores.
🔗 https://woocommerce.com/posts/category/add-to-cart/
Mailchimp – Popular email marketing platform with integration options for WooCommerce.
🔗 https://mailchimp.com/
Mailpoet – WordPress and WooCommerce-focused email marketing service for transactional and automated emails.
🔗 https://mailpoet.com/
AutomateWoo – Automation plugin for WooCommerce that enables custom workflows and marketing automations.
🔗 https://automatewoo.com/
Klaviyo – E-commerce-centric email marketing and automation platform, cited as a leading choice within Shopify and WooCommerce ecosystems.
🔗 https://www.klaviyo.com/
MailerLite – User-friendly email marketing platform with WooCommerce integrations.
🔗 https://www.mailerlite.com/
Metorik – Advanced analytics and reporting tool for WooCommerce, referenced for its integrations and AI-powered features.
🔗 https://metorik.com/
Audio Timestamps
- 00:00 Email as a relationship tool
- 06:04 The power of email data
- 10:09 Improving email marketing strategies
- 11:57 Discussing email marketing platforms
- 17:17 Setting up post-launch email strategy
- 18:19 Importance of email marketing effort
- 23:40 Improving email communication strategies
- 25:16 Struggles with email marketing
- 30:44 Discussing abandoned cart emails
- 33:11 Email’s high return on investment
- 38:17 Using AI for ecommerce insights
- 40:03 Creating AI-written emails
- 44:41 Mass proliferation of AI newsletters
- 47:14 Improving onboarding and customer relations
- 49:00 Building post purchase email flow
- 52:10 Discussing AI as a data tool
- 55:19 Session wrap-up and thanks
Transcript
Episode Transcript
Katie Keith:
Welcome to do the Woo, the podcast where we talk about all things WooCommerce. I’m Katie Keith, founder and CEO at Barn2.
James Kemp:
And I’m James Kemp, the core product manager at WooCommerce. And today we’re going to be talking about email marketing for WooCommerce stores. What’s working, where merchants are falling short and what to prioritize if you want to get more from your list.
Katie Keith:
And for that we’ve invited Simon harper, email and WooCommerce expert. So thank you so much for coming on, Simon.
Simon Harper:
Absolute pleasure.
Katie Keith:
Could you give us a bit of an overview of your work with, well, both email and WooCommerce?
Simon Harper:
Yeah, I’ve been doing this for 17 years now and the email came in about nine years ago on top of that. So my foundation has always been WordPress and into WooCommerce and technical SEO and then I’ve now got Shopify Partnership as well, which you’ve become very familiar with, Katie, over the last while and, and the email focus has been really nice as well. Niching down sort of into E commerce, that side of things and deliverability. So I was Ireland’s first ever MailChimp partner, also a Klaviyo partner, but I try to be platform agnostic.
James Kemp:
That’s awesome. 17 years. So that. That’s mostly WordPress. Right.
Simon Harper:
I think WooCommerce was 2011 static HTML as well before. So I was a slightly late adopter to WordPress. Yeah, we can go back to our Dreamweaver and Serif days and front page and other things.
James Kemp:
That sounds good. Well, thank you to everyone who submitted questions for Simon. On social media, we also have a live chat on whatever platform you’re watching this on. So feel free to ask questions as you’re listening. And before we dive in, feel free to follow us on X. We’re at do the Woo. You can also subscribe to our YouTube channel at do the Woo podcast and you can visit our website@dothawoo.com well, so
Katie Keith:
let’s go into email marketing. I was reading on HubSpot that email marketing, apparently it returns an average of between 36 and $42 for every dollar spent, which is pretty amazing ROI. So let’s start. Simon, I’d love to hear your view on why you think email marketing is such an effective channel.
Simon Harper:
I think for me personally And I think it’s about relationships. So it’s, it’s a relationship you build over time and it’s something that’s very difficult to get across other channels, particularly whenever it comes to paid acquisition and ads. And it’s hard to get relationships through SMS and things like that there. So email is definitely part of lifecycle marketing. It shouldn’t be a channel that’s done in a silo, but to use that term owned, which I know is debatable now within email, but it would be traditionally known as an own channel, a channel that you would have a huge amount of control over, which you wouldn’t have normally whenever it comes to algorithms etc. Although obviously we now have the AI inbox coming from Google and Google I O’s announcement a couple of days ago. So that’s going to change things up a little bit. But. But it is something that you can pretty much control at every part of the journey from whenever somebody first subscribes to whenever they leave and everything in between. It’s very hard for any other channel to sort of touch that level of relationship. And if you gather the right data, the best information and the best relationship that you can have with a person happens in email. It doesn’t happen outside of that anywhere else perhaps in person.
James Kemp:
How do you think it’s going to change with Google’s new features?
Simon Harper:
Us is going to get them first as always and then it’s going to roll out grads over time through their paid plans down into their lower tiers and it’s going towards sort of a hyper personalized inbox where Katie’s inbox would be very different from mine and as your would be James as well. So time will tell. European regulators will probably have a say in it whenever it comes over here, which is why it’s also taking its time to roll out. But I think in the long run, if you do have a personalized AI inbox that is genuinely useful, I’m for it, but time will tell.
James Kemp:
I can’t imagine what that would look like at the moment.
Katie Keith:
Depends on how organized you are. If you’re someone that is near inbox zero and all of that anyway, then it probably wouldn’t do much. Whereas if you’re one of those chaotic types that have thousands of emails, maybe it would be a game changer.
James Kemp:
Yeah, that is true. Yeah, mine’s very much. I try and keep it pretty empty. Any email that I have in my inbox is something that I need to reply to or action in some way. The statistic you gave is interesting. The 36 to $42 for every dollar spent. When I was doing email marketing for Iconic, we never saw that level of return on emails.
Katie Keith:
I know what you mean, but we’re not very good at email marketing. We don’t.
James Kemp:
Yeah, we’re not. We should have hired Simon.
Simon Harper:
Yeah.
Katie Keith:
I think the principle generally with marketing is that the more targeted the marketing, the higher your conversion rate, the higher your ROI. So that’s the whole funnel thing, isn’t it? So I think with email it’s relatively targeted because they have chosen to sign up hopefully if you’re meeting the law.
James Kemp:
Yes.
Katie Keith:
Let’s not go into cold email, which is a very different thing and that has very low ROI, I suppose days.
Simon Harper:
It’s one of those great examples, I mean as well of depending on what data you’re gathering and how you have it mixed in. But email’s a great way of, of gathering zero and first party data. You can’t really get that from ads or other channels like that there. And as well, whenever it comes to email, depending obviously on what platform you’re using first of all and second of all what data you’re gathering and third, what you’re trying to measure it is by far the greatest return I think that you can get on any investment. So it may not be that 36 to $42 for you, but it could be something much greater than that in terms of a relationship, in terms of lifetime value, whatever you want to look at. Cost per acquisition is obviously an interesting one in email. Now there was the newsletter conference happened in New York a couple of days ago I think it was. And they’re seeing a big shift now from lists and I’m sure we’ll talk about this later, to much more smaller focused lists than bigger lists now because it’s always been about size previously with email list but that’s couldn’t be further from the truth and I’m glad that that focus is kind of coming to the mainstream now.
James Kemp:
Yeah, that makes sense. I think the, there’s the concept of your email list is a warm audience.
Simon Harper:
Right.
James Kemp:
So they, they already know who you are because they as long as you took the, the correct route they signed up themselves or you know, approved the sign up to be on your email list. And I would expect that definitely helps with conversion because if you’re doing cold advertising on, on Facebook or Google, I think Google can be fairly warm that because you’re, you’re reaching people that are searching for specific terms and looking for a specific solution and they have that Intent, I guess. But they, they may not know your brand whereas your email list in theory does. There’s many different kinds of email marketing, right. That you could implement on. On an E commerce site, on a WooCommerce site specifically, what sort of email marketing have you seen a typical WooCommerce store, what would you recommend and what have you seen those stores doing?
Simon Harper:
Well see this is the interesting one because if you’re in the, and I’m sorry to mention Shopify again, but if you’re in the Shopify ecosphere, it’s kind of that thing of automatically people go to Klaviyo for that and that’s kind of. There’s a known relationship there. And certainly whenever it comes to WooCommerce that would kind of be the dominant platform that I would see. But there are the interesting about WooCommerce is a lot more platforms that are actually also involved in that. And whenever you see other E Commerce or other ESPs that aren’t specifically focused on E commerce like Klaviyo would be, it’d be. It’s interesting to see what campaigns that people actually run. So again, this is another interesting one that we could go down a rabbit hole in. So please feel free to stop me rambling at any point. But it depends where you are, what campaigns you run and what your goals are. So for example, if you are onboarding everybody as you should be and following best practice guidelines and following legal guidelines, there’s certain things that you can’t do in certain countries whenever you’re marketing stereotypically. A lot of the companies I would work with or I would see are US based stores, which is kind of. No, they’re catching up with the eu, but it’s still mostly we’re just going to bombard everybody with everything. We’re going to do browse abandonment, we’re going to do product browsing full stop before it even gets to the cart or the checkout. And we’re going to do lots of other things and that works for some people. But then your options can be dramatically limited if you’re only stuck at abandoned carts or abandoned checkouts or you’ve then got your pop up flows and your signups from those. And that’s another interesting one that we can talk about or the traditional one of sign up in the footer. So I guess you see those sort of main types of a welcome email sequence and it’s maybe one email or at best and if it is a proper sequence, they’re kind of poor, they’re very Basic and it’s not looking at the customer acquisition source. So what page did those people land on rather than they just landed on my site, you know, what product were they on, what product category were they in? Where was the refer? Did they come direct, did they come from Google, did they come from ads? And then those kind of levels, you can make things much bigger. There’s a much bigger opportunity there. And then as I said before, you’ve got the traditional checkout and abandoned carts or educational flows. Educational flows are something I don’t see that often. So it’s kind of a post purchase, check in type thing. And then the sort of infamous gray area of informed consent that a lot of big retailers I would see use is, hey, you bought product X from us 12 months ago. Your warranty is about tonight. Are you interested in? So it kind of depends what line you want to tread. But there’s just, there’s a wealth of things that WooCommerce stores do, but there’s a wealth that they don’t. And I think what’s interesting is if you, if I was to compare a WooCommerce store in terms of email marketing to other platforms, it. They’re definitely quite basic in how they use email marketing and I don’t know if that is a WordPress thing or a WooCommerce thing or what because there’s some fantastic tools out there. And WooCommerce, thankfully in the last couple of major versions and then I’m done has brought some fantastic changes to the email market templates and how you can basically integrate those and customize them. So well done team on that. Very good.
James Kemp:
Yeah, I wonder if it’s because maybe platforms, SaaS, platforms like Shopify have very specific paths to enabling this stuff. Whereas with, with WordPress and WooCommerce it’s a lot more flexible, like installs a platform that suits you best. Yeah, and maybe there’s. We probably don’t push any one platform enough or maybe a lack of like education around the different kinds of marketing emails that you could send. Because yeah, out of the box we have very much transactional emails. Yeah, there was a team actually working on a review, like leave a review type email. So when someone purchases a product they would get an email, you know, X number of days after to encourage him to leave a review. So that, that’s something that we should hopefully see coming to Core soon. But yeah, we don’t have any like life cycle type emails in Core like the, the education style ones that you mentioned or any sort of like Automated on a sequence type of emails. Unless you use something like MailPoet or Automate. Woo.
Simon Harper:
That’s a good point. And I think that’s, you know, what you were saying earlier on there about not pushing one particular SaaS provider. So it depends what you’re using as well, what their capabilities are. I mean, MailChimps and what not. Skyverge, Kestrel have been doing to overhaul them. And another team were working on overhauling and fixing MailChimps, for example, connection with WooCommerce because it was horrendous, which wasn’t a Woo issue, it was a MailChimp issue. So you were kind of limited in some of the things you can do. Whereas Mailer Lite, for example, I found quite intuitive and it’s very easy to connect and use up with some clients. Mailer Press has obviously entered the market now and I’ve been using Metorik with customers or Metric. I always debate with Bryce what on earth it’s called. I don’t care. It’s awesome. Been using it for 10 years. But it’s interesting to see that basic things like more and core in terms of reviews are coming because what you had said with another point with Shopify. So Shopify has flows built in,
Katie Keith:
which
Simon Harper:
is kind of almost. It’s a base layer for any new customer coming in that they have this set of basic and I mean basic email marketing tools that you can use, but at least it’s something to get started. And then they hop on the klaviyo.
Katie Keith:
It is an app though, isn’t it? Flow. It’s a free app that you can install, but they make it more prominent in the admin. Yeah, I think it’s right that Woo core doesn’t have flow sequences built in. I don’t think that core territory. But to me this is a wider issue. With a big proportion of WooCommerce stores, they set up WooCommerce, which is great for a good cross section, but they don’t further optimize their store to the extent that they could. There are so many different examples of that where they just stick with what the way it comes. I think Simon’s right about the improvements wu’s made to the default emails. But for years you could just tell whenever you bought something from a site, you knew they were using WooCommerce because of emails, which they didn’t even change the color of to match their branding. Even things like store layouts, like a lot of our plugins change the layout of your store to be more optimized for different use cases and most stores don’t even think that the default layout isn’t appropriate for their products. And email is another one that why aren’t Woo stores thinking of these opportunities to optimize their business whereas stored with other platforms are?
Simon Harper:
I think no, I know this is a controversial topic, but it is something that we might consider adding as a nudge in the onboarding. And I know the onboarding is constantly being reviewed and obviously then we get into the community questions of well, which services do we recommend? But maybe it could just be an educational piece of email marketing, such a vital part of this. Have you considered it? And obviously depending on where you’re at in the onboarding stage, maybe there would be. There’s always recommended plugins but this is where it makes things more difficult because it’s not just about the plugin in this instance, it’s about the SaaS that’s behind it.
James Kemp:
Yeah, it’s definitely a challenge. I think that kind of nudge in WooCommerce is more acceptable than that kind of nudge in WordPress because WooCommerce is a business, we have partnerships with email providers or email service providers like that. So yeah, I think there may be some nudge or recommendation to install an email plugin. I’m not sure which one it would be. Yeah, it’s interesting because I think there’s two different kinds of people that set up the site, right? There’s a merchant with no real like technical understanding, maybe mild technical understanding that set it up and maybe don’t configure it properly. And then there’s the agencies that have more of an understanding and maybe they’re not thinking about the, you know, post launch unless they’ve been explicitly asked to consider that.
Katie Keith:
And they naturally wouldn’t think about post launch until they get to that point. They’re busy setting up this, storing the onboarding and it’s not exactly a one click setup. Doing email sequences really involves a lot of analysis and writing. Even if you get AI to do the drafts, you really need that strategy of how you’re going to drip feed information and so on. I got at Barn 2 we’ve got 19 WordPress plugins, most of probably 15 of them have probably a 3 year old sequence of MailChimp emails that send initially very frequently and then only every few months. And each time it’s we’ve really thought about what might be a feature that they’re not using after two years that they don’t know about. And that’s not a quick thing. For you to set up and you wouldn’t do that while you’re building your store. That’s like a post launch task. Unless you have a massive marketing team,
James Kemp:
it’s probably not even a developer agency person’s job to do that. It’s a marketing like you say, a marketing person’s mindset.
Simon Harper:
I was going to say something similar and that’s the thing I think with a lot of WooCommerce store owners or store owners in general, they are aware that they have to do email marketing but because it’s something that they have to do, they don’t actually realize how much effort you should be putting in and the return that you then will get on. It’s like anything, you know that if you put a lot of effort into it or you can those people that set and forget email marketing are just leaving so much on the table. I’m not even talking about revenue. I’m talking about those opportunities to build relationships and partnerships or gather important data that could inform your store in terms of right. What products do we need to drop, what products do we need to add in or modify or oh here there’s an issue here with the customer journey even you know, why are people dropping off at this point or why are people not connecting further? So it is an interesting one of whose role actually is it And I don’t think it is. I think it’s the business owner should definitely have. This is the problem of being like small companies or big companies. Obviously your resources are limited, they really are. But maybe there’s some opportunities for the educational pieces on Add to Cart which is pretty good. I, I like that on the WooCommerce blog and that Add to Cart series. So there’s some. Because I don’t see much talk about email marketing even in there there is content points.
James Kemp:
Yeah, I guess my concern is I know developers and agencies read the WooCommerce blog but how do we get those blogs in front of merchants who aren’t, you know, who are more than likely not reading that unless they have some sort of technical understanding of what they’re actually using like WooCommerce and WordPress. So maybe some like in app level educational stuff would be useful. I wonder though what there’s obviously some very complicated setups that you can do with email and I know Katie, I’ve seen some of yours and they’re very complicated but what are some of the more simple things that every store owner should have as like a minimum?
Simon Harper:
Yeah, and I think that’s the thing you can make. Something is as complicated as you want it to be and sometimes you do need to have flows that are complicated. But one of the biggest mistakes I see just in general is overcomplicated flows. And the more complicated flow becomes and more difficult is to manage, particularly if there’s more than one person in a team. If you’ve got the skill to manage those complicated flows and they’re set up for a reason, then by all means, you know, perfect. But I think where you kind of have to start whenever you have those opportunities is you look at the entire customer journey and start with those basics. So you look at your welcome email and make it a welcome sequence. A good point is maybe around three emails. So whenever they come on board, you need to pick avenues for where you want them to go, where you want them to go based on their decisions in that first email. So the first email that you will get in your welcome sequence in general industry wide is going to be the most opened and most kicked by far. That is where you’re going to get your biggest engagement. So that is your choice of right, I want them, I’m going to give them 2 CTA, 1 CTA and want them to go down this route or I want them to go down that route and off you go. And it can kind of come in from there. And then the big ones outside of those initial welcomes are your abandoned cart and your abandoned checkout. They’re two different things. Abandoned carts aren’t used as much as abandoned checkouts would be, which a much more traditional thing. I know there might be some semantics around here being from different countries or whatever we’re from, but most people will hopefully know what I mean by that basket. Is not checkout basket is cart. So there you go. Um, reviews is a very big one. So reviews how we get those, how we incentivize those after a purchase has been made. Because we’re so busy these days sending out a normal review email and getting a review back is so difficult and that that review is so valuable to the merchant. It’s unbelievable because you can then turn that review into content that can be used across social media in paid ads wherever you want. It is so valuable. So it’s how we get that incentivize that or work on those and then obviously you’ve some other post purchase flows in terms of depending what product they’ve bought, whether there’s a follow up piece further down the line, whether there’s an educational piece and I do see browse abandonments I see rarely but they do kind of happen. But it’s very difficult to do those without being creepy because hey, I saw you looking at this product you didn’t buy. Why did you not buy? It’s, you know, it’s, it’s a bit weird. Yeah a bit weird. But I think it’s keeping those sensible. And then whenever you have and now this is the hardest simple thing to do and this will sounded very Irish but that will make sense in a moment is whenever you actually have somebody on your list. One of the biggest things I actually see with the stores is they don’t actually send an email so they’re stuck on these transactional emails that you had mentioned earlier on James. But they don’t actually send out an email whenever they should be sending out at minimum a weekly email just purely of how the inboxes work, how the inbox deliverability works across different whether you’re using Gmail or Outlook or Apple Mail which I find a close second to anything that’s Outlook. You know to appear actually in the inbox you need to be consistently speaking to people and if you, if you send out you know, a welcome email, a few welcome flows and then never anything else until somebody buys something, why bother? You need to be regularly talking and communicating. So that is one of the biggest things. It’s so simple and yet merchants just don’t do it.
Katie Keith:
Yeah, see this is a problem for me. I have a confession which is that I hate email marketing largely because bothered I hate receiving marketing emails in most, at least 80% of circumstances. I didn’t appreciate the email. So I’m really sensitive of bothering people and yet I know all the data about how the more you email people the better there’s obviously a limit, but that limit is so much further than what I would be comfortable doing. Even on Black Friday, you’ve got people emailing every day for two weeks and things like that. I did an episode of WP Product Talk maybe two weeks ago with Josh Daly from Docspot, and they’ve just done a product launch week in which they emailed their customers every day about the same launch to highlight a different feature and create a real buzz around it. And I just can’t bear to bother people that much, which really restricts our email marketing.
Simon Harper:
Yeah, I think there is that massive inbox overwhelm, which is partially why these useful AI overviews have come out, whereby they’re saying, look, we’re going to look at your inbox, we’re going to surface the emails. This is how they’re generically sort of working they that are most relevant to you. And then we’ll provide contextual summaries how those summaries work, depending on how well the emails are coded semantically and various other things. But that’s for another topic. But it is. But the. The counter argument to that, and I feel you like obviously being in email marketing, my inbox is assassinated on a daily basis with the amount of emails that come in. But if you’re not doing it, your competitor is. So it’s how you do it without annoying your customers. And one of the best ways to actually do that, and a lot of people don’t do it. And this is a limitation of the ESPs. And often depending on what pricing tier that you’re on, is have a really good preference center where people can go, hold on, I want to pause emails. Just pause them for a week, pause them for two weeks, or I don’t want to be part of your Black Friday promotion. Something like that. There. There are ways to give people a break and I think a lot of people will appreciate that from brands as well if they know. Right. I can go on, pause for a little bit and then come back in
Katie Keith:
MailChimp, because I haven’t figured out exactly how to allow people to unsubscribe from the Black Friday emails in MailChimp. I cannot work that out.
Simon Harper:
Yeah, it’s. Well, that’s a MailChimp thing. Their preference center is interesting, which you can’t also turn on properly if you have their GDPR settings turned on, which is a bit of a weird one, but it is kind of that. It’s respecting the inbox or respecting through the user and they will hopefully return it and by knowing that you’re listening to them, that’s the biggest thing. So with email, I’ve said before, and I need to get that across like repeatedly that a relationship isn’t a one way thing, it’s a two way thing. So if you do it’s, it’s a classic thing of marketing. There’s a guy I know, a really good friend of mine, Andy Jarvis, and he talks about talk to your customer. Email is one of the best ways to talk to them, but you have to listen as well. So yeah, if you, if your ESP provides it, one of the biggest opportunities that you can have whenever it comes to E commerce is a preference center that people can choose exactly what they want to hear from you.
James Kemp:
That’s a good idea. On the technical side, I wonder if in MailChimp, could you, could you send an email asking if they want to know about Black Friday and if they click yes, they get, or if they click yes or no, they get given a specific label.
Simon Harper:
Yeah, there’s always ways around stuff and you can even use external preference centers as well if your ASP doesn’t provide one. But pretty much whenever you’re specific, like all the ESPs call them different things, but essentially what you’re saying there is a customer clicks on something, they get tagged and then your automation or flow is assigned to that. So it’s just like, right, they’re in this, so they want to hear about Black Friday, they click no. So they’re not part of this. But again that’s when you have to stay on top of things and stay organized because the flow might be quite simple. But if you haven’t set up the segmentation correctly and the conditions, then you’re in trouble.
James Kemp:
You mentioned about abandoned car and abandoned basket. I recall when I was setting that up. It’s, it’s complicated. Right. With GDPR, um, I know there was some ways around it that by entering your email you’re like, yes, it’s kind of thing.
Simon Harper:
So yeah, it’s that legal disclaimer thing. I’m not a solicitor, I’m not a lawyer, all that kind of stuff. But it’s informed consent. Whenever they get to that stage, particularly the checkout, and they’ve gone all that way, even Parsi filled it in, put in their email address, they’re pretty much saying, look, I’m ready to buy. And there’s the safe assumption of if they haven’t bought something legitimately could have happened like my house is on fire or I need to go and get the kids, which is something less dramatic than your house being on fire. But you know, there can be legitimate reasons for that. Cart or basket or checkout haven’t been abandoned. There is some tools as well. For example, the likes of Motorcy who actually offer an option that injects into the checkout where you can opt out of abandoned checkout emails if you wish.
Katie Keith:
Yeah, Premiums are good at that as well. They have. They keep it subtle, but there is an option to opt out.
Simon Harper:
So. And I think that’s brilliant because it’s a bit of again, that relationship building and added value where you’re going, look, we can do this, but we know it might annoy you, so if you want to not get these emails, that’s fine. So. Yeah, and the thing is as well is it depends on what that abandoned cart is. That’s so along the same lines of what you said is if you want to stay in the. On the right side of the law, on informed consent, your cart has to contain just those products because it’s abandoned. One, you can’t go as an upsell or a cross sell at this stage of abandoned. You know, we thought you might be interested in these or, or you can’t. That’s, that’s, that’s naughty then.
James Kemp:
It’s marketing, right?
Simon Harper:
Yeah,
James Kemp:
yeah, it’s. It kind of ties in the preference thing.
Simon Harper:
Yeah.
James Kemp:
And it ties into what you’re saying at the beginning about small niche lists, that it’s better to have a small list of people who want to be on the list. Yes, it’s like a massive list where, you know, many of them don’t even know who you are and don’t open the emails. So that’s something that I regularly did with the iconic list was to do. I think they called it like a re engagement campaign or something like that, where you, you just email them again and say, do you actually want to be on this list? If not, click here and unsubscribe. I like that approach.
Katie Keith:
Yeah, we’ve started doing that as well and also sometimes automatically pruning them if they’ve not engaged for years or something. In fact, our MailChimp plan only goes up to 40,000 subscribers. So that’s a really good motivation for me. I had to do a bit of pruning yesterday because I needed to import some people.
Simon Harper:
Yeah, that’s another reason genuinely as well that’s argued for amongst the email community, whereby it saves you as a business owner an awful lot of money having, you know, having a more engaged list and having huge amount of People that never do anything but cost you money.
James Kemp:
Yeah, yeah.
Katie Keith:
And that goes back to the ROI thing we were talking about. That email has surprisingly good roi. That’s probably largely because it’s actually quite cheap if you think about it. Because if you’ve got a decent sized list then for the amount of work, like if I could just email 40,000 people in like 20 minutes or something like that, then maybe that’s where the ROI comes from.
Simon Harper:
Yeah, and I think the HubSpot one’s always interesting because of litmus have done ones over years as well. It depends what industries have been surveyed and what you know their costs are and what they define as a return and whether ads are included or not. But I think in general still without question industry wide email is by far still the biggest return on investment you’re going to get. And it’s particularly depending on whenever you bring in. Now I’m not talking stressing this, not talking about buying lists, but whenever you’re doing paid acquisitions, so you’re paying for ads to get people subscribed onto your list. There’s lots of things now where you know the cost of acquisition of those traditionally has gone down to almost nothing. So. And there’s tools out there like Sparkloop, which kit bought out but it is platform agnostic whereby if you even get the, the money right there, the return on investment is insane because you actually end up can you can get paid to onboard your own subscribers depending on what way you have been, what way other, how can I phrase the subscribers has been referred to you from other sources. So basically you can pay X but you get paid Y in return and it can end up being a positive. But obviously the downside of having subscribers brought onto your list have come from a paid ad in general, they are gonna be not as engaged as somebody that has come to you. And as you said at the start of the conversation, Katie, they have chosen themselves to be on your list and organize and engage and those are always the customers that tend to have a higher. In fact, actually for the stores I work across, the ones that would have the highest LTV in lifetime value in terms of those have come from organic, they’ve actually come from Google Search, they come from Bing and they have actively looked out and find these brands themselves for whatever reason, find the products they like, connected with it and gone on from there in general so far that’s what I’ve sort of found in my experience and I’m working with mostly stores in the UK and Ireland and some in the US
James Kemp:
Yeah, that’s. I think that’s very important when you pay to acquire subscribers. Is it a case of like you could imagine a Google Ad that leads to a landing page where, you know, they, they opt in to enter their email. Is that the typical path or is there like other.
Simon Harper:
Yeah, that’s, that’s money. It’s just essentially a landing page with a MailChimp sign up form or whatever, whoever you’re using. It’s one actually that I’ve been asked to build today, but I’m doing this because it’s much more fun the other one tomorrow. But it is because those landing pages are obviously, they’re great because they can be left online in Evergreen as well and they’re there for AI to find or whatever. But you can have so many landing pages obviously depending what your campaigns are, working across those. And they’re really nice. They’re. They’re nice ads in general, that kind of work.
Katie Keith:
Yep. So you mentioned the essential word AI a minute. So let’s move on to. That has to be part of every podcast. So I’ve heard some e commerce store owners using AI in particularly innovative ways recently. Like one person I know is using AI to write custom emails for each customer, but not like through the chat, but automatically based on knowledge of things like the purchase history. So the idea is that it will be fully automated and that the AI will just be given free reign to write these custom emails, which seems terrifying to me, but this, they, they seem very excited about it. So beyond using AI to just draft emails, which everybody’s doing, do you have any advice on how people can use it creatively and effectively and safely for better results?
Simon Harper:
Yeah, the, the AI thing is evolving so much. So for example MailChimp have Intuit Assist, which used to be their own like native AI for helping you automate flows and write everything. I think they’ve just followed suit with deals with OpenAI and Anthropic, which kind of fall in line with what Klaviyo was doing and their Claude MCP and where that has gone, which is what intrigues me a lot more than just writing emails. So it’s basically Claude has full access to Klaviyo for example, and can just build out the flows and the emails and analyze data and segment stuff. Now I will say there is a fantastic document from the team at knack. There’s two of them that have looked at the big AIs. And first of all, can they actually build emails properly to meet coding standards to work in as many inboxes as possible and they can’t and so they don’t even get close. So there’s always going to have to be work there around it. If you are actually coding and building emails, never minding writing them, depending on what integration you have with E commerce and where you kind of want to go from there, where I see AI at the minute being most helpful is whenever you’re kind of merchants, look at it to analyze their customer data, organize their work, help make better decisions. So look at customer behavior, summarize purchase histories, look at segments that they’ve maybe missed, look at drafting different kind of approaches and integration. So for example Mator. Again, sorry, it’s. It’s what I mostly use with Shopify. I know there’s lots of other things out there and WooCommerce, but it has its own integrated AI as well where you can talk to it and it’s brilliant and it takes all the data that is natively in WooCommerce but is kind of hard to access. It’s getting better, but it’s, it’s much better whenever it’s in there and you can talk to it and have this conversation about okay, tell me everything I need to know about my customer or tell me X, tell me why or look for gaps. I think that’s the biggest thing. So whenever it comes to data analysis and segmentation and opportunities for now, I think that’s where the biggest opportunities are in email as opposed to just writing or designing an email. Because writing an email in your tone is very difficult and I’m intrigued how this company has done it because it screams cold email to me. I know it’s obviously not, but as that’s a very traditional tactic that cold emailers will use with placeholders and metadata and pulling everything in and dropping it off. But that also terrifies me because I would want to read each email before it goes out, particularly when it comes to E commerce because there’s so many opportunities for that to go wrong and there to be repercussions.
Katie Keith:
That’s so true. We’ve got a comment from Moon at Noon who says AI seems to make a lot of errors and that’s in terms of factual errors but tone wise and just sounding like AI is very hard. But I, I’m improving on that. Like I’ve decided I Yesterday I built a tool where I hooked up MailChimp to Claude and had it analyze the tone of our emails which by humans and I basically created the WordPress plugin for my team where they choose the type of email like, is it a newsletter, promotional update, whatever. And then it will write the email in our tone in a format they can paste into MailChimp. So it’s still got a human, but it’s actually doing pretty well. When I tested it and I was able to use the text that it wrote so you can get. It sounded like a human. I’ve also hooked it up to my voice profile, which is something that James released. If you. You go. So if you do the work, you can get it sounding human. But to let it loose is another thing.
Simon Harper:
Yeah, I think like I use AI as well to help me write my newsletters in terms of ideation even and things like that there when there’s days where I’m so tired from my kids, it’s just kind of like my critical thinking is out the door. So I need to have that sort of base sometimes to jump off. But. But then you do require. Because for example, I’ve a newsletter come out on Monday and I was reading through it and looking at some of the ideas and I. I literally said to Claude, did you just make up fact number six? And yes, I am sorry. And I’m like, why? Why complete? Why do that? Or. But the tone thing is brilliant. And I agree what James has done there, I’m like, I use whisper flow and a few other things and have trained at how to understand and write how I talk. So again, it’s that effort. How much effort are you willing to put into personalizing your AI and having those skills and everything in place first of all, as the bedrock and foundation? Because if you have that, then it can certainly write a much better email for you. But I think in terms of what I alluded to at the start of this question and the document that Knack had created is in terms of actually building those emails themselves technically and getting them into the inbox, not having errors and issues. They’re accessible and people can actually read them. They have a long, long way to go.
Katie Keith:
Yeah. And it is a huge investment to put that time in and have it sound real. But hopefully the rewards will be worth it if it does get you over that barrier of not having the time to be creating the number of emails that you’ve said we should be. Simon.
Simon Harper:
Yeah, I think it’s just AI definitely has a place as long as it’s just not AI for the sake of it. I got a classic thing and email definitely has so much potential for it.
James Kemp:
I have two thoughts. One, I remember experimenting with kind of moving away from email templates and into more like traditional looking emails with you know, just a standard text introduction and paragraphs and sign off. I wonder, I guess there’s certain scenarios where they maybe work and when they don’t. Like I don’t know if they would work for abandoned cart for example
Simon Harper:
but
James Kemp:
I think that’s interesting. That seems like something that AI might be better at is that kind of email than like more of a templated one. And the second thought I had is I wonder if the concept of AI helping with email marketing will evolve from it writing the content or you know, preparing the flows into it. Like you not having content or flows and the AI is working in the background like understanding the customers and knowing what email to send to them.
Katie Keith:
Exactly. Yeah, that’s a whole other step. But that would be pretty cool and potentially has better results than all of our. We talked earlier about complexity and all these automations and the overhead that is to maintain that would actually get rid of all of that if you could get the AI to that stage.
Simon Harper:
Yeah, I’m sure they’re working on it. I’m sure they have a behind the scenes just waiting for the next stage of we need you to spend more money, we need you to burn more tokens.
James Kemp:
Yeah, for sure. What do you think would be a terrible way to use AI? I guess to just.
Simon Harper:
In email or just in general?
James Kemp:
In email?
Simon Harper:
In email. So this is an interesting one because there are companies and I’m not envious, I’m not jealous, although the money would be nice. But there are companies that exist already that and they’re very explicit upfront about what they do. So there’s one in the UK will not name them and what they do is also perfectly legal. But it is, I just, it would crack me up. So they basically have a landing page and they have literally about 500 AI newsletters now it used to be like 50 and then it was 100, now it’s more and they’re all identified into niches so they look at you like builders and plumbers or builders and plumbers in certain areas, you know, those types of things or school teachers in that type of thing. And literally what it is they are AI newsletters that send out daily or weekly campaigns and it’s just troll data pulled from the RSS feed scraped all that kind of stuff. But giving people the key information they need to know in their specific areas, say for example, what’s going on industry wise, all that kind of stuff, those types of things just. I don’t understand it because essentially it’s Just the most soulless, horrible thing I’ve ever seen and yet it works. So I hate it. And that is a terrible use of AI. I think it’s not advancing humanity at all. It’s just advancing somebody’s pocket. But, you know, it works at the same time, I think if you’re using another kind of thing would be the AI. Ultimately taking it a step further, which is the most obvious1 is AI cold email. Oh my goodness. I think we’ve all experienced it. It’s horrendous. Absolutely horrendous.
Katie Keith:
Oh, and AI job adverts, because that’s kind of via email these days and that’s horrendous too. Not job adverts, but applying to a job. I’ve been on the receiving end of that and it’s not nice.
Simon Harper:
I am tempted to take up acquisition offers for how much people think my company is worth. You know, it’s because it’s so not worth what they want to offer.
Katie Keith:
But you know, so let’s talk about, let’s bring it all together. If you’re running a WooCommerce store, how can you put some of this into action? So Simon, I’d love to know, what would you prioritize for the biggest impact email wise, if you were running a WooCommerce store?
Simon Harper:
Are we talking about email or are we talking about something else? Because if it was something else, it would be shipping and taxes. So I’m going to say that now. And if you put a gun to my head, it would be shipping over taxes.
Katie Keith:
Oh, you can come on to do that next time.
Simon Harper:
Yeah, that’s fine by me. But yeah, the biggest impact I would start with is just basically going back to those two things I sort of said that people are doing, but they’re not doing well and is prioritizing both the onboarding, the welcome sequence and then the post purchase experience. So don’t worry about anything sort of in between. You can, as we were discussing that earlier on, that’s a huge amount more work to regularly have those newsletters going out or those regular email campaigns actually engaging people in between. And those are important. But the priority first of all is getting people onto your list, getting them on, well, sending them where you want them to go to maximize sales and also making sure that they’re getting the right information at the right time. That’s the biggest thing. And then those post purchase flows or what I would like to call in sort of like e commerce nourishment or relationship building. So it’s like, okay, you’ve purchased something, particularly if this is a one time purchase, how do you then communicate with that person if you know this is going to be something they’re only going to buy once, could they gift it to somebody else? Maybe put that seed in their head or. Look, if something does go wrong, this is what you can do. It’s unlikely, but this is what you can do. So not just those checkout, abandonment cart, abandonment basket, whatever you want to call them, it’s the post purchase flow itself. So whether it’s that review which is so important to you as a business, that is a huge one to prioritize because that review is worth so much these days. And then obviously the educational thing. So it’s that welcome onboarding and post purchase.
James Kemp:
Do you think because email’s a long game, right? You, you’re not going to get massive results from one email.
Simon Harper:
No.
James Kemp:
It’s like you say about building that relationship and building trust as well. I think that you’re not just you know, a salesperson trying to sell them something. So when you say post purchase email, the flow I envision and implemented previously, okay, they’ve bought a plugin from me. The first email is going to be how to set it up, where to find support, that kind of stuff maybe directly in the email or maybe it’s links out to documentation, that kind of thing. Not trying to upsell at all anything at that point. And then I, I think we maybe had one or two after that which showed them how to do things that they maybe didn’t know how to do with the product. And then potentially after that it would be, you know, by the way, this other plugin that we have also works really well with yours. What do you think that kind of thing is that, Is that what you envision with a post purchase or is there like some do’s and don’ts around that?
Simon Harper:
I think you’ve done that quite nicely. You can have my job. Although please don’t because you’re doing very good things at Woo. So stay where you are, we’ll do a job.
James Kemp:
Swap one.
Simon Harper:
Yeah, I think that is kind of the biggest, the biggest thing whenever it comes to post purchase. I like what you kind of said at the end there with whenever we do have that opportunity to cross sell and upsell it is further down the line sort of towards that perhaps natural end or yeah perhaps natural re engagement point. So yeah, the way you describe that is perfect.
Katie Keith:
And the other time to do it is Black Friday. So that is the most effective emails we do all year and we do different emails to existing customers and potential customers because we’re encouraging them to take different actions. And the ones to existing customers actually generate a lot more revenue than the potential ones. So it obviously depends what you’re selling. Some companies genuinely have nothing to upsell. If you only have one product and it was a lifetime purchase, then there’s nothing to upsell, is there? You just need. Even retention isn’t going to get you any more money. But assuming you have multiple products or potentially upgrade options on the product they’ve bought, then Black Friday can be very effective for sure.
Simon Harper:
Very much so.
Katie Keith:
Well, before we finish, we’ve got some comments about AI. I think AI is a misnomer because it’s far from intelligent. It cannot think, it can add like a calculator. Language takes imagination. We can’t even get autocorrect to work right. I think it’s a lot more than that, but we need to be aware of the limitations and manage it. What about you two?
Simon Harper:
Google’s bringing out its version of Grammarly called Proofread, so as part of all of this new AI overview. So we’ll see how good it is at doing that. But yeah, no, I think there’s some good points in there, but I think AI is definitely progressing.
James Kemp:
Yeah, I understand the point that, okay, it’s not necessarily intelligent, but it has the capability to intake a ton of data and give you a reasonable assessment or output based on that. So in my mind, it’s a tool like it, it takes, it can, it can process, you know, all of your store’s data in 30 seconds and if you were to do that yourself, it would take a lot more time. So maybe it’s not intelligently thinking like a human would, but it’s, it’s processing data more intelligently in terms of how it ingests it, it knows how to interact with, knows the context of what you’re asking for and it can give pretty good responses. And I think if you, yeah, don’t, don’t believe everything it says. You know, trust your instinct as well. You still have to have some sort of domain knowledge in whatever you’re researching or working with. But it’s definitely something that I think everyone should be using.
Katie Keith:
Yeah, yeah, it’s a tool and it’s the most useful tool we’ve ever had if you use it. Right, agreed. Well, Simon, thank you so much for coming on and for people with their comments as well. So where can people find you online?
Simon Harper:
You get me on Twitter or X, whatever you want to call it for me, it’s Twitter, LinkedIn and Bluesky. The easiest place to get all of those is SimonHarper link.
James Kemp:
Awesome. Thank you. We have a couple of shows lined up.
Simon Harper:
Right.
Katie Keith:
Good thing to talk about. Radical Speed Month.
Simon Harper:
Exciting.
Katie Keith:
Exactly. Because we want to know what came out of that.
James Kemp:
Yeah. So that finishes tomorrow. The month is up. So we’re hoping to. I expect by the time we do our next podcast, we’ll have some, like, assessment of how that went. I know there’s, you know, hundreds of projects that have taken place within WooCommerce. We’re talking, you know, tens of projects. So it’d be cool to analyze some of them, look at some of them and consider, like, how the, how the experience might influence how we work in the future. Maybe with a guest. We’re not sure yet, but after that we have a special one with Tamara Neeson, who is our CMO from WooCommerce, which will be a very cool conversation. So we’ll put some official dates out once we have them locked down.
Katie Keith:
Yep. So again, please subscribe so that you don’t miss those new episodes that we have just talked about when we announce the dates and so on. The easiest place is go to dothewoo.com and you can access all the different ways you can subscribe from there, depending on how you like to listen to or watch podcasts. Well, thank you so much for watching. Bye.
Simon Harper:
Bye.
James Kemp:
Thanks all.