Callum: So today on our podcast, the In Reviews We Trust podcast, I have with me Chase Dimond. Chase is the co-founder of Structured. Chase operates multiple newsletters, and I seriously don't know where or how he finds the time to do them. He's also just launched a brand new SaaS product. I'm super looking forward to this episode. If you don't already follow Chase on Twitter, make sure you do. He talks about email marketing, deliverability, and really provides some great insights on how to hit that inbox with your email marketing and get the most out of it.
Chase, thank you so much for being on today's show.

Chase: I'm pumped to be here. How are you?

Callum: Good. Very good. Very good.
So, Chase, how did you find your way into this world of email marketing?

Chase: It's a long story, but I'll try to make it short.
At the age of 13, I was diagnosed with Crohn's disease, and at 13, I didn't actually know it because I was sick for an entire year. So after being sick for an entire year, I took it upon myself as a 14-year-old to learn marketing, specifically non-paid marketing. So I started doing fundraising and awareness for this charity, and I was sending emails to friends and family, buying ads in the papers, and organizing restaurant fundraisers.
So email kind of started then, and my marketing journey kind of started through that. Throughout high school and college, I had different jobs and internships where I was doing cold email outreach. I fell in love with email as a channel in my teens and reconnected with it in high school and college through jobs and internships.
After graduating college, I used email in a really interesting way, different from what I do today. I was using cold email to acquire massive amounts of users, whether it be newsletter subscribers or users for ed-tech platforms.
So when I graduated, I was building an education technology platform that connected students at college campuses with others in their classrooms to make learning more collaborative. To explain simply, I connected students at large campuses to create study guides, share tests, notes, and quizzes.
We went to the college directories, found students’ emails, and sent personalized emails saying something like, "At UCLA or USC, we’ve built this organized drive where if you upload your documents, you can get access to others’ documents in your class." It was almost like building a social network for college students.
Then from there, I took that skillset and built a travel series, growing it to 500,000 email subscribers in 10 months by aggregating data from Instagram. We identified people using hashtags like #travel or who followed Nat Geo or tagged places like Bali. We’d get their emails and send them personalized messages, such as, "Hey, we both follow Nat Geo, and you're based in Irvine. We wanted to invite you to join this travel newsletter and its Facebook group for like-minded travelers."
Long-winded story, but it started with charity fundraising and awareness, jobs, internships, acquiring users, and now, over the past four years, I’ve been specifically focused on eCommerce email marketing. One of my buddies saw that GDPR was coming, California privacy laws were on the way, and cold email was becoming a gray area. So, I transitioned to opt-in email marketing— all white-hat, very by-the-book today. That’s the short version of the long story.

Callum: Wow. Wow. That's an incredible journey. I love reading your content. I think your content is original. What’s the best-performing piece of content you've done so far in the newsletter?

Chase: Well, first off, thank you! To answer your question, I have this guide on the welcome series for non-buyers. If you think about an eCommerce brand, we all acquire subscribers through forms, whether that's a pop-up, a flyout, an embedded form, or even at checkout. For the first three—pop-up, flyout, and embedded form—those subscribers trigger what's called a welcome series for non-buyers.
At my agency, we have a four-part email sequence. The first email is sent immediately, welcoming people to the list and delivering any offer or discount that was promised in the pop-up. Most brands offer a percentage off, a dollar amount off, or free shipping. That’s what email one covers.
If email one doesn’t convert, email two focuses on the "what’s in it for me" angle. We address the quality of the brand, how it’s different and better than competitors, and what the subscriber gets as a customer. One example is Magic Spoon, which sells keto-friendly cereal. In their second email, they have a graphic comparing their product to competitors—Magic Spoon with 3 grams of net carbs versus competitors with 21 grams. That visual paints a clear picture of their benefits.
If the person still doesn’t convert, the third email highlights social proof and popular products. This includes media features, celebrity endorsements, or influencers praising the brand.
If they still don’t convert, the last email invites them deeper into the brand’s community—join the Facebook group, Slack channel, or reply with questions.
So, the article was about this four-part email sequence for the welcome series.

Callum: That’s super interesting! I love these sequences and the psychology behind them. They’re fascinating. In that first step, when you capture the email, there are different solutions like Klaviyo, PushOwl, and others. Which one do you recommend, or does it depend on the retailer?

Chase: I don’t think there’s a one-size-fits-all. I’m biased because I run an agency, and we have over a hundred clients. For us, having everything native in Klaviyo is really convenient because managing different platforms across different accounts can be a headache.
If one account uses Klaviyo, another uses Octane AI, and another uses Privy, it’s a lot to juggle. So for us, Klaviyo isn’t necessarily the best, but it gets us 80-90% of the way there, and it’s good enough. For a brand, Klaviyo is great because it’s built into the cost of the platform, but there are other good platforms too. For example, Octane AI is great for quizzes that recommend personalized products. There are tools like Privy, Justuno, and WisePops that also work well.

Callum: What about SMS? Do you get involved in SMS marketing, or do you stay away from that?

Chase: It’s interesting. I’m an email guy through and through. We’ve started offering SMS as a service, though I personally don’t know much about it. SMS is easier in that you don’t need long-form copy or complex designs, but it’s more delicate because of compliance issues. If you break rules around opt-ins or don’t provide clear opt-outs, the fines can be hefty.
That said, SMS is great for immediate engagement. The VIPs—about 10-30% of your email list—are the ones who will sign up for SMS, and the revenue per recipient is strong. You need both email and SMS, though. If you’re starting small, I’d say start with email but collect phone numbers for when you’re ready to implement SMS.

Callum: Yeah, that’s good advice. Walk before you run, especially with SMS. We collect reviews via SMS at REVIEWS.io, and conversion is really high, but you have to be careful with spam and compliance. Timing is crucial too.

Chase: Absolutely. With email, we send about 2-5 emails per week per brand, depending on the business. With SMS, it’s more delicate—usually once a week or every other week works best. Anything more and you risk overdoing it.
We try to mix community-building content with product updates and sales. For example, we send out playlists, recipes, and tips alongside promotional content to build a bond with the audience.

Callum: Community is hot right now in eCommerce. Everyone’s talking about it—how to keep customers loyal and how to get them talking to other potential customers. Who do you think is doing this well with email marketing?

Chase: A couple of brands come to mind. One is Olipop. They’ve nailed everything—product, email marketing, and customer experience. They do an amazing job. Another is Judy, which sells emergency preparedness kits. They’ve done a fantastic job blending products with education and content.

Callum: Yeah, I follow Olipop on Twitter, and they’re always sold out. Brilliant marketing!

Chase: Another brand I’d mention is CrossNet. They invented a sport, built it from scratch, and turned it into an eight-figure brand. They’re doing everything right, from going viral on TikTok to hosting tournaments. It’s pretty inspiring.

Callum: That’s awesome. Switching gears a bit, deliverability is a big issue in email marketing. It’s not just about hitting the inbox but making sure the email is engaging enough to get opened. Do you have insights on improving deliverability?

Chase: Definitely. There are five factors that determine whether someone opens your email:

1. The “from” name—Is it familiar and recognizable?
2. The subject line—Does it catch attention?
3. The preview text—That’s like a second subject line, so use it wisely.
4. Timing—When you send the email impacts its open rate.
5. Where it lands—Inbox, promotions, or spam folder?
   To improve deliverability, start by sending to your most engaged subscribers, like those who’ve interacted within the last 30 days. Focus on high-engagement flows like welcome series, abandoned cart, and thank-you emails. Also, make sure low-engagement flows like re-engagement campaigns don’t drag down your deliverability.

Callum: We send hundreds of thousands of review collection emails every day, and timing is so important. We don’t want to send them too early before breakfast, but we also want to hit inboxes after the first check of the day.

Chase: Exactly. Another thing people don’t talk about enough is consistency. I send my newsletter every Monday at 8 AM local time. Over time, people know to expect it, so even if it lands in promotions or spam, they go looking for it because I’ve built that pattern.

Callum: Why did you choose Fridays for your second newsletter?

Chase: I send my main newsletter on Mondays, so I wanted to bookend the week by sending something on Fridays too. It keeps me top of mind over the weekend, and then on Monday, they see me again. It’s a strategy I’m testing, and so far, it’s working.

Callum: I like that! What do you see changing in email marketing over the next 12 months?

Chase: I think deliverability will remain a big issue, but I also see email becoming more interactive. There’s a technology called AMP (Accelerated Mobile Pages), which allows users to interact with content directly within the email, like filling out surveys or making purchases. It’s underutilized, but I think more companies will adopt it.

Callum: Interesting. We’ve experimented with reviews inside emails, but we find that linking to a separate page often works better. AMP might be a solution to that.

Chase: Yeah, AMP could improve the experience. It’s not supported by all email clients yet, but it’s gaining traction.

Callum: Tell us about the new SaaS tool you’re launching.

Chase: I’m building a tool called Email Up—we bought the domain emailup.com. The idea is to make it easier to design beautiful, high-converting emails. Right now, our agency has a full team of designers and developers to create and code emails, but that’s expensive and time-consuming.
With Email Up, we’re creating a platform with pre-built templates and easy customization, allowing users to export directly to platforms like Klaviyo or Mailchimp. We’re also integrating features like AMP, countdown timers, GIF creators, and dark mode previews. The goal is to make email design accessible and efficient, so anyone can create high-quality emails without needing a full design team.

Callum: That sounds huge! I can see the demand for it. Are you launching this as a Shopify app, or will it be outside the ecosystem?

Chase: Both. It will be a standalone platform, but we’re also launching a Shopify app so users can dynamically import products from their Shopify stores directly into emails. It’s in submission now, and we’ll have it ready when we go live.

Callum: I think it’s going to be a massive success. Your approach to email design is much more advanced than what most platforms offer. Are you in beta right now?

Chase: We’re in alpha at the moment, with about 10 users testing the platform. We’re moving into a private beta soon, inviting people who filled out a survey about their current email design process. We want to keep it small at first—maybe 100-150 people—so we can get detailed feedback, fix any issues, and roll out to a larger audience later.
This way, by the time we go public, we’ll have more features and a smoother experience.

Callum: That sounds smart. Private beta is the way to go. It keeps things controlled and manageable.
Chase, you’ve been a fantastic guest. Thank you so much for sharing your insights. If anyone isn’t following Chase on Twitter, make sure you do—I’ll drop his Twitter handle in the show notes. Good luck with Email Up, and thanks again for joining us!

Chase: Thanks so much for having me! I really appreciate it.

Callum: Thank you for listening today. In Reviews We Trust is a bi-weekly podcast, where I bring you advice and insights from brands that are taking the eCommerce world by storm.