The challenges of growing a newsletter in big companies – Naomi West


In this episode, Naomi provides insights into Invoice2go’s efforts to grow their newsletter program. She shares learnings from experiments with segmenting their audience and testing different approaches, as well as the real-world limitations and challenges in executing tests and getting buy-in.

Key Timestamps

00:53 – Naomi discusses her role at Invoice2go and the goals of using email to drive activation and monetization

02:15 – Inheriting an existing email program and getting a “blank slate” for an overhaul with the rebrand

09:17 – Three pillars of the customer life cycle

15:18 – Starting a segmented newsletter strategy for different audiences

17:40 – Testing content performance but unable to find statistical significance

20:32 – Changing no-reply to actual email for a two-way communication channel

24:55 – Intermission questions

29:33 – The three newsletters Naomi picked for Invoice2go

35:07 – Successful testing of personalized outreach from faux personas

38:46 – Call to action versus call to value test

43:35 – Doing list hygiene for the Later newsletter

45:00 – Steps taken to turn engaged subscribers into paying customers

47:13 – Key learning from the time at Later

Show Notes







Bridget Casey



Naomi West – Twitter

Naomi West – Instagram

Naomi West – Website 


Lesley Sim Twitter

Lesley Sim Website

Stay in touch

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Twitter Website



If you’re a news or media publication running on WordPress, check out Newsletter Glue. It cuts your newsletter publishing time in half and enables you to manage your entire newsletter ops in WordPress. Go to to learn more. Welcome to Sticky, the podcast that helps you build a must-read newsletter through actionable case studies and playbooks. Today’s guest is Naomi West. I’m so excited to have Naomi on the show.


Right now, she works at Parcel, which recently got acquired by CustomerIO, managing marketing and go-to-market. Before that, she was a lifestyle marketing manager at Invoice2go, where she worked on multi-channel product activation, monetization and retention. She’s also had stints at Later, Instagram’s first marketing scheduling tool, and she was a customer onboarding manager at Braze.


Today she’ll be talking to us about her time at Invoice2Go, where they focused on segmenting their newsletter program as a key growth strategy. Hey Naomi, so glad to have you on the podcast. I’m so glad to be here. Email is a huge passion of mine, both in my day job and outside my day job. So I’m happy to be here to talk more about email. And you have your own newsletter as well, right?


Yes, I have a newsletter where I don’t abide by my own best practice of predictable sending cadence, but I’ve titled it Slow Emails and it goes fairly and frequently whenever I have actual like email related news to share or you know a new tool or kind of resource in the space. So I try and send once a month, but sometimes it ends up being like once a quarter, which is okay. As long as I set the expectations right from the start that it’s going to be a slow email, I feel like it’s fine.


Yeah, I get that email. It’s really good. Thank you. So when we were chatting on Twitter DMs, as people do, you were talking about your time at Invoice2Go and how you guys spent a lot of time trying to grow your newsletter strategy. So you had your overall newsletter and you tried to segment it. Can you talk us through a little bit more about that? But first, let’s just talk about what you were doing in Invoice2Go.


Mm hmm. Yeah. So I joined Invoice2Go in beginning of 2021 ish as an email marketing manager. And I was joining a team of one existing email marketing manager and a director of lifecycle marketing who also managed SEO and App Store optimization and Invoice2Go.


is pretty similar to its namesake. It’s an invoicing solution meant for small and medium sized businesses. And what we really wanted to do was encourage activation of those that had signed up looking for an invoicing solution to hopefully reach these kind of aha moments with the product so that they would be hooked enough to want to subscribe to a paid plan and then use us for all of their small business needs moving forward.


They were more than just an invoicing solution. They offered quotes that freelancers and small and medium-sized businesses could send out to their clients and payment tracking and kind of a dashboard where they could communicate back and forth with clients as well on invoices and quotes and estimates. So it was meant to be this kind of small and medium-sized business hub. So my role was to use email as well as in-app.


and push and SMS to create these relationships with these individuals to hopefully gain their trust and educate them on the tool and then hopefully gear them towards monetization. And how much do you work with in product onboarding versus kind of external multi-channel marketing type of onboarding? Yeah. So it’s always interesting. I find.


as like an email or lifecycle manager that is jumping into an existing setup, because you usually have teams that will own certain communications before you get there. And so, Product had developed an onboarding process where during signup, you would be asked, you know, what type of business you are, and kind of questions that would hopefully assess your needs to better guide you in the tool. So when I joined that kind of,


in-app experience of here are all these screens that you kind of go through as you’re going to sign up to the product. Those were already in place. And my job kind of moving forward was to inherit a lot of the strategy from product marketing as to what features were going to be released soon and what features we already had that were high in activation and do more like one-off in-app messages in the form of onboarding or…


feature education or feature awareness. So although, you know, I didn’t necessarily get to own kind of the experience where I’m guiding people through the app on day zero or day one. My touch points were more so like, okay, you’ve already gotten through that process and you’re here, what should you be aware of? So it was kind of owning the segmentation after they had gone through the initial screens and gone through, you know, all the data collection of.


Give us your email address, tell us your industry, tell us your business size, tell us how many people you work with. And then I got to do the fun part of like, Hey, if you’ve been in the tool for 14 days, here’s the thing you should check out or if it’s day two and you haven’t signed your first invoice, here’s an in-app to guide you in that direction. Nice. Yeah. And can you share a little bit more about what the state of the newsletter was like before, like, or when you just joined? Yeah. So.


The email program that we had when I had joined was fairly transactional in content. Like it felt robotic. It didn’t feel necessarily like an easy invoicing solution that you could just pick up and do on the go. And we had a newsletter that was very product focused in the form of here are these things that have happened over the past month and you should go do them.


What myself and my other colleague wanted to do was we wanted to take this whole side of brand marketing that was being built and the communities that were being fostered outside of the app itself and bring that personality into our email marketing. And so luckily when I joined, we were actually like, I think the day I signed my offer, they had signed a contract to move ESPs. Oh, wow. So when I got in there, it was kind of like, hey,


you can start basically auditing what we have right now in our current ESP, and you can scrape whatever you want and bring it into the new one or start fresh. And then I think the second week that I was there, they announced that they were doing a full rebrand. And so it was pretty much like, you know, whether it’s the newsletter strategy or the automations, like we have an opportunity to fully change the design and the voice and tone. So that really set us up for success where we could say,


OK, we haven’t done this before, but we’re now going to use all this data that we’ve collected on a user, asking them where they’ve come from, whether it’s the female founders kind of community that we fostered. They had a Facebook group that had a lot of people interacting. Or if it’s the small business kind of segment of users that have said, I own a small business, or a group of freelancers, we wanted to lean into all those aspects and try and provide content to them both in.


educating them on the tool, but also here’s this brand new kind of content that we produce that we think will be useful to you, whether you’re in one of those three categories. So blank slate? Yeah, complete blank slate, which is a dream in my world. I think inheriting a program can be so difficult sometimes because you go in and you’re all like doe-eyed thinking there’s a lot of possibility, but then you realize how many emails are in place and you’re like, oh no.


There’s so much happening here, but it was really like a dream scenario where I could go in and things were set up and the touch points were set up, but I had the opportunity to either rip them out or redesign them or rewrite them, which is so cool, or implement brand new ones. So what was the first, I’m guessing you went in and started with a high level strategy and like you mentioned an audit to see kind of where things were and how you wanted to set things up for the new ESP. Which ESP did you?


migrated from and to by the way. We migrated from Cordial to Braze. I think probably me having a background in Braze was the reason why I was hired on to the position. Thanks. And I wasn’t involved in the Cordial conversation. So I didn’t necessarily know what pain points they were having there, but I was brought in primarily, I think for my expertise with Braze. And that was great. It was an easy tool for me to adopt. I know there’s a lot of tools out there. So.


It was nice to be able to step into a familiar one. And so what was the first few things that you did once you got, you know, started implementing Braze and implementing the new strategy? Yeah. What was the strategy? Yeah. So when we were looking at the life cycle, the way I look at a customer life cycle, especially in the form of like owned channel marketing, is I break it into three pillars in my head and on paper.


But I break it into activation where people might be, you have their email address, you’ve acquired their email address, they’re in your system, but they might not be ready to monetize yet. And that’s kind of the second pillar. And then the third pillar is retention. And what I wanted to do along with my team was kind of set the best possible activation window up.


to make sure that we were covering our bases with educating people on how great the product was and talking to kind of the customer success team or the customer support team to see what common questions were coming in about how to use the product so we could nip them in the bud right there and then, and then start to kind of gear up the communication towards that second pillar, which is monetization, talking about…


why this is a product they shouldn’t live without and why we’re better than competitors without saying like, don’t go use QuickBooks or, you know, the other kind of realm of invoicing solutions, but, you know, set the stage up for why this is a fantastic tool. So what I did first was, I believe we pulled screenshots of every single email that was coming out of Cordial before we ported it over and we popped everything into Miro to look at.


And we had many Zooms where we would go in and just write commentary like, this is outdated or, you know, this touch point on day 10 of the customer life cycle doesn’t really make sense with this specific feature anymore. And it was really like a brainstorming and whiteboarding exercise. And that was really what we started with. We wanted to get the onboarding automations in Braze. Cause that’s one like,


your probably highest engaged audience group, because they’re net new to the tool, and they’re going to have the highest intent to either click or sign up. So in the grand scheme of things, we were thinking about what’s the best content for warming up our new IP address, because we needed to do an IP warming. And- Why did you have to do IP warming if it was kind of like, you’re already sending ongoing emails, and you had all these things set up already?


So we didn’t have anything set up yet in Braze. And with Braze, you get a brand new IP address, as well as we were not sending from a subdomain in Cordial. So we wanted to, one, start sending with a subdomain so that our parent domain was more protected when it comes to sending practices. And then, two, the IPs, we just couldn’t transfer them between Cordial and Braze. So had to start fresh, which is a nice,


I don’t mind an IP warming because you get to kind of say, this practice that we’re leaving behind of sending to a massive list, is that the best practice? Can we leave some of these subscribers behind if they haven’t opened or clicked our emails in six years? Yes, we should absolutely do that. So it was just a dream to be able to go in and strategize what’s going to be the most impactful for IP warming as well as most impactful for the business to set up right away.


And can we have a healthier list? So that was kind of my initial strategy with everything. And then the rest kind of followed. I think when we’re being meticulous at auditing all of our emails, the newsletter strategy kind of came into play as well. And we got to ask ourselves, we have all this data available to us now in Braze that we can segment with or personalize with, what should we try?


And I’m lucky because my manager was just so open to testing and she always wanted to kind of hear new ideas from us. And she’d allow us to kind of run with those ideas and see them through, which is really cool. So at the time, you started as an email marketing manager, is that right? And so your manager was kind of looking over on a multi-channel level? Yeah. So she managed myself, my colleague,


who was also an email marketing manager. And then we both, I think became life cycle marketing managers because we were just owning many more channels than just email. And then there was another individual who focused on SEO and web strategist, and then like someone who focused on app store optimization. Cool. So when it came to email, you and your colleague were really like the ones driving the whole thing. Completely. Yeah.


Because Braze offers like multi-channel automation, it fell, email and in-app and push notifications all fell into our bucket, which I think is why our titles were changed later on, which I think I do feel like there’s a lot of email marketing managers out there who also toy around with SMS and Bush and in-app depending on the tool that they have in front of them. Yeah, that makes sense.


We were just starting to talk about newsletters and the strategy that you employed. Can you share a little bit more about that? Yeah. So one thing that brand marketing really focused on was fostering smaller communities. And this was outside of the beginning newsletter strategy and how we wanted to segment our audience. But what we kind of discovered was.


There was this whole community called the Female Founders that people could sign up to and get an invite to a Facebook group with other female founders. And it was this sub-community with an Invoice2Go. And same with the small business community. And then we had a freelancer community as well. And when you think of it, the personas that we had,


hypothesized that were coming to Invoice2Go, they kind of fell into one of those categories. So what we wanted to do with the newsletter was, you know, try out with dynamic content, is there more valuable pieces for female founders than freelancers, than small businesses, and try out kind of a stint of crafting this really personalized email newsletter program. So that’s kind of what we kicked off.


trial and error. Newsletters are interesting because I find it’s hard to create a North Star of success with them. Like it’s, is it list growth? Is that like what you’re aiming for? Or is it click through rate? Like are you trying to get traffic to your website? Or is it open rate, which isn’t the most reliable metric anymore? And that kind of metric change came into effect when I was at Invoice2Go. And so it kind of threw a curve ball at us for…


We could try out the segmentation. Are we wanting to just give them content and have them respect us as the trusted source of industry knowledge for the content that we’re providing them? Or are we trying to get some secondary action out of them that would positively benefit the business with some metric that we could show for it? That was a struggle, I think, we grappled with during that time of trying to run this newsletter strategy.


is how do we define success of it? You know? Did you end up coming up with anything? I think what we ended up doing was measuring click-through rates just to understand if the content was what we thought would be the best for those audiences. So we didn’t necessarily say, OK, this month’s newsletter had a higher conversion rate than last month. We would say, did articles in the female founders newsletter


have a higher click through rate than when everyone was in a bucketed newsletter approach on its own. So is the segmented approach more impactful than this previous benchmark that we always had where we just assumed everyone would like the same content? We tested it out for a bit and I do believe that it looked higher but there was no statistical significance to say that it was actually higher. Like I think we looked at it and we were like…


This is great, you know, it’s a 1% click through rate. There’s no way that this could be, you know, not statistically significant, but time over time, it kind of came back with just like flat results, which is not necessarily a failure, I would say. It was fun to test out, but I think in our case, we realized that the time and effort that we put into creating this large segmented kind of newsletter campaign.


didn’t have the uplift versus like just going broad. So prior to the segmentation, Invoice2Go was sending one newsletter to all three segments with the same newsletter, is that right? It was, we didn’t segment, it was everyone was just bucketed in to one kind of approach. And the newsletter content was primarily product focused. We would talk about how the product was positively benefiting people.


What changed with the segmentation was we would look and say, you know, does the small business segmentation, would they enjoy this new evergreen piece of content that the content marketing team wrote and is now on our blog about how tax season is approaching and here are all like the tax benefits depending on where you live in the world. And would the freelancer group, would they for this evergreen section piece?


Would they benefit from a case study on a freelancer that became successful with Invoice2Go and saved 10 hours of time? And so it wasn’t necessarily either, like it wasn’t apples to apples when we were comparing newsletter to newsletter, right? But we were just kind of assuming and hoping that these individual approaches had impact. Yeah, it’s kind of sad that you weren’t able to see kind of statistical significance over that because you just talking about it.


seems like, again, like to me, it seems like it would have been amazing to receive such like customized newsletters. Were you able to get any qualitative feedback from people receiving the newsletters that like they much enjoyed or much preferred the segmented approach? Yeah, so that was another thing. It was really difficult because the replies fed into customer support. It was so difficult for the Lifecycle team to get access to.


those replies that were coming in. We originally had the OG newsletter actually was a no reply address. And I went in there and I was like, no, no, this is so valuable to be able to have this two way street with subscribers and for them to be able to come back, whether it’s just like a, I loved this content or like, hey, I can’t log in. Like.


we should use email as a two-way channel. It drives me nuts when no replies are there. Like, ugh, it’s just such a missed opportunity. And I know you said I could swear, but this would be where I would swear because I hate no replies. So there was a lot of pushback from customer support during that time when we were like, we don’t want a no reply. And they were like, we don’t have time to manage replies.


We were like, who does it go on? Like who gets the weight of these replies coming back in? And I think the solution was there was going to be an inbox where the replies would feed into, but it wasn’t going to be actively monitored. Like someone would go in and maybe once a week, take a look at any replies. But when it came down to myself and the other members of like the lifecycle team, it was difficult to try and get like exported replies out of whatever tool they were using to manage them.


and into our hands. So I’m sure there were replies, and I would love to see them, but it was just really difficult to try and get access to them. Oh, that’s too bad. I think when it comes to trying to make the business argument of, you know, the CS team has so many things on their plate already, and when they are to say, what is this newsletter doing? And we’re like, we’re just building relationships.


It was hard for them to kind of say, okay, we can dedicate time to that because we weren’t saying we’re driving upgrades or we’re winning back people. There wasn’t a direct measurement of that even though we could measure it. And I think we did in Amplitude, which is what we used. And we could see that those actions were happening. It was hard to make a business use case for, we need more dedicated resources for the newsletter. And this is why you should give them to us when we were just like,


building relationships. And to me that is important but hard to explain sometimes. Everything that Naomi just talked about is actually just the reality of how companies are run and I find it so valuable. First, she talks about a failed segmentation experiment and that’s the reality of most experiments, right? Like they fail or they need to be tried again in a multitude of different ways before they finally succeed.


And the reality on that is that most companies don’t always have the resources, will or appetite to keep on trying those experiments to get them to succeed. Then she explains how they couldn’t get qualitative data on the segmented newsletters because newsletter replies are fed into customer service. And that’s not the team that she’s on. And again, like, having newsletter replies and emails fed into customer service makes perfect sense.


And then she talks about how it was difficult to make the business case for customer service to get them to change where those replies were going. And again, that makes total sense. Why would customer service spend their valuable time and resources on a relatively small change that doesn’t particularly impact them when they could spend time onboarding new customer service agents, improving their documentation or something else that would move the needle for them?


All of this is so valuable because so many interviews or articles talk about best practices, but they always gloss over the real world limitations. And hearing Naomi’s experience from deep in the trenches really adds a lot of colour to what really happens and why execution is so much harder than just giving advice. In this case, like in most cases, nobody was doing their job poorly or maliciously. It’s just big company things.


I love how open and honest she was about all of that and her willingness to share that with all of us.


Let’s go into our intermission. I have a bunch of quick questions that I’ve prepared to get to know you better. Feel free to answer in a word or a sentence or however much you want. Okay, I’m ready. So the first question is, what’s your favourite ice cream flavour? Mint chocolate chip. Oh, that’s one of my favourites. Without a doubt, there’s no question. Yeah. So no context, spicy or sweet? Spicy. I love spice.


I can’t handle it very well, but I really like it. What’s the spiciest thing you’ve ever eaten? There is a chain chicken wing restaurant. I don’t even know if I’d call it a restaurant, but a chain chicken wing restaurant in Canada, maybe the States as well, called Wings. And they had or have this wing that they call the Bobby wing and it is the hottest wing I’ve ever had. And you sit there and you try it. They only give you one.


And you just cry the whole time because it’s so hot. And then they also give you some kind of like slushy, milk slushy on the side that tastes horrible but it’s supposed to be cooling. That is probably the hottest thing I’ve ever eaten that I didn’t enjoy. Like I did it and I was like, why am I doing this? How much does one wing set you back? You know what? I think it was like, I was gypped because I’m pretty sure I probably paid like $15 for it. It was the experience. Yeah. Maybe the milk drink also.


was a charge, but it wasn’t a cheap wing. Oh man, that’s crazy. Yeah. Okay, beach or mountains? That’s a tough one. I feel like I want to say beach, but on a day where it’s like 21 to 26 degrees Celsius, cause I’m not really good in the heat. And if it’s any more than that, I’m not going to enjoy the beach cause I’ll be too hot. But I really like the mountains too. So I want to say beach on a medium temperature day.


What’s your favourite beach? I live in Vancouver and there are some really nice beaches here that are just quiet. There’s one called Spanish Banks that I love. Otherwise, probably the beaches in Tofino, which is off of Vancouver Island’s coast, are the nicest beaches I’ve ever been to. Cool, I’ve never been to Vancouver before. I love to visit. You gotta come. Yeah, it’s not too bad. Outside of work, what’s something you’re really, really into?


Reality TV, which I don’t… I don’t know if that’s something I should be as into as I am, but probably Reality TV and I’m super proud of it. I love keeping up with my Reality TV survivor, all the housewives, Amazing Race, Top Chef, you name it. And then I also am really enjoying the new Zelda game right now. And… I saw you post about that on Twitter. I love Zelda. Yeah, I can’t deny it. I love…


video gaming and watching reality TV and email. Sometimes all at the same time. Yeah, most of the time actually I’m sitting on the couch doing all three. Okay and last question, would you rather shave your eyebrows for a year or get a bright pink mullet also for a year? I would shave my eyebrows off. One, I feel like that’s actually maybe trending right now. Ah, I didn’t know that. And could be…


Maybe a thing. And a pink wallet. I like neutrals. Like I’m a lot of my wardrobe is neutral colors. So the pink would completely throw things off for me. It has to be the eyebrows. Yeah. All right. So while we were talking, I got ChatGPT to write you a limerick about all of your favorite things. Oh my God. What does it say?


Alright, let me read it to you. There once was a woman, Naomi. Mint chocolate, mint chopped chip ice cream made her dreamy. Spicy wings she’d devour at Spanish banks, Spent an hour playing Zelda as if it were easy. That’s so nice! Those are all my favorite things. That’s like actually like an incredible poem. I really enjoy that. Hey, thanks ChatGPT. Yeah, who would have thought?


Yeah, now you have a little keepsake from our time here. Yeah, that is true. That’s great. That’s something I would frame. Yeah.


So what were the three newsletters that you sent? You mentioned dynamic content and you also mentioned kind of cherry picking relevant articles from the content marketing side of things and adding them into the newsletters. Yeah, like if we zoom out a little bit, how were the three newsletters, I guess, conceptualized and like how do you think about each of the three? And also, sorry, just as a reminder for people, the three newsletters were female founders, small businesses and freelancers.


Yeah, so we worked really closely with our amazing design team to create a base template that would essentially be duplicated every time we wanted to create a new version. The strategy was we wanted to include one customer case study every time because the content marketing team was focusing really heavily on creating customer case studies that could live on the website for SEO but also be repurposed for stuff like this.


So for every newsletter in each segment, we wanted to utilize a customer case study. And then we wanted to include a product feature, whether it was something new or something that maybe had a minor update that would benefit that specific segment. Sometimes it ended up, if we had a tier one launch, it would end up that we would use the same kind of product feature for each, but cater the copy.


to how a freelancer would benefit from it. And then I believe the third section was an evergreen piece of content, like the articles on how to save during tax season or how to avoid work from home burnout or how to manage, think for the female founders, we really leaned into burnout and balancing family life and stuff like that, not to make assumptions, but we definitely did.


Yeah, so we tried to pick an article based on what we thought everyone would like that was new on the website. Cool. Okay, so and then how often were each newsletter sent? Once a month. So basically we would, I think we tried to send mid-month every month. And we would work in almost like sprints.


So one week would be for copywriting, and then I would brief the design team on any updated imagery and assets. And they, I think, had like a 10-day turnaround, or maybe two weeks. So it was kind of a rush to get the copy, who was also edited and worked on by a copywriter, get the copy done with the strategy we had in mind, and then get the design team briefed. And then we would spend.


like a week on the build and QA and getting stakeholder approval. So every newsletter like seemed to take about a month. And it’s funny because I’ve worked on other newsletters where it’s just like, go, go, go. And like Parcel’s newsletter, I write it the same day and I send it. Doesn’t have any images, but like it’s same day. I was just about to say, yeah, it’s same day delivery. I get it out the door like within an hour. So it’s funny. Like.


When you zoom out and you grow teams, how much added time it can add on, which is good in some scenarios. Like some days, you know, even at Parcel, I’m like, oh, I would love to have an image in here. I’m a horrible graphic designer, so it wouldn’t work for me, but yeah. Yeah. I guess that’s the balance, right? Like if you’re working for a smaller team, like Parcel, it’s easy to just kind of get things out the door and I’m the same way.


But then once it gets bigger and the stakes are higher, then you need like the extra week of QA. You need the professional designers to do stuff. Because like, you don’t want to be responsible for your Canva design thing going out to everybody. Absolutely not. No, no one would be liking what I would be putting out if I was in that position and in voice to go. But yeah, it also like, you know, we had put and created really fantastic.


Briefing processes too with this ESP transition, I think we wanted to understand business needs more and understand what the content brand team was working on and what could be used for the newsletter. And so with that newsletter overhaul, it was a great way to reach out to other teams and say this is our new strategy. If you have a product feature that you think would be beneficial to be promoted, let us know and same with content marketing.


And it’s funny with product marketing and product, usually the marketers blast to know that a product feature has been launched, right? But in this scenario where you kind of like an extend, you extend an arm or like an olive branch in the opposite way, they’re like, hold on, let me tell you about this thing that’s coming up. And they’re like all giddy to include you because you’ve promised that you’ll promote their feature. That’s really cool. I bet that helped a lot.


What other key things about the newsletter segmentation strategy would you like to share with us? One thing that we tried out that was super interesting was like a one-to-one like reach out where we created this faux persona and we did an email signature sign off like Amy from customer support and we tried that for a while and that was an email where we knew that there were replies because customer support was shouting about it.


They were saying, we’re getting all these replies to this one email where Amy’s reaching out and asking them information from them and it was like a faux persona. There was someone definitely named Amy and the company and we used her photo for this for this email, but it was so interesting like instead of the blanket team from friendly address or like a blanket email where you’re just assuming you don’t need to sign off from it when we tried that strategy.


We had not only the conversion events, which we tied to all of these emails anyways, just to see if there was movement in them, even though they weren’t our North Star metric. Like the click-through rate was higher, the conversion events were higher, people were replying. Like they felt maybe some sort of like weird pressure on them to engage with this email from Amy, but it was such a cool strategy and it was a great indicator to


customer success or customer support, that email is meant to be a two-way channel. And more people are engaging when you give them an opportunity to reply. And our whole job is to build relationships and see customers succeed, right? So this is a strategy that’s opening the door for that. And that was a great learning. Like we didn’t have, it was hard to pull out learnings when you’re not comparing apples to apples and the audiences were different. But that one strategy


was one that I pulled out and I was like, this is one I’m going to remember for a long time. Nice. And were you able to double down on that strategy and kind of implement it a bit more? Yeah, we implemented it in our onboardings where we baked in some of those touch points at key lifecycle moments. So when we wanted someone to monetize, then they were so close to it, or we thought they had hit the aha moments with the product.


we would implement those touch points to go out automatically to say like, Hey, I’m Bill here from Invoice2Go. Like, I’m do you have any questions about the tool? Like I’d love to be helpful to you in some way. And it was always replies would come in like, Bill, I’m so sorry. Like I’m going to check out Invoice2Go tonight. So the strategy, yeah, the strategy was one that was very easy to mirror. It was an easy one to just point to for how successful it was.


We didn’t necessarily say, oh, this is going to be successful if we hit like a 5% higher click-through rate, but when we put a generic email next to this, like one-to-one touch point, it was so clear that everything was better. So that was really great.


Newsletter Glue cuts your publishing time in half by enabling your team to publish newsletters the way you publish articles in WordPress. Find out more at Now back to the episode. Another learning that we did in one of the newsletters, and this is a test I love to talk about, we ran like a call to action versus call to value test. And I find that in a lot of SaaS,


tools these days, you’ll get emails being like, here’s this new flashy feature, go do this, like try it now. I’m like, what am I trying? Like, I don’t understand. It’ll be some interesting like email with like graphics that I don’t fully understand that it’s meant to look like a product screenshot. And then it’ll be like new feature, like try it today. And it loses me every time. And so what I did was I took.


whatever the product marketing manager gave me in terms of this new feature that we were creating. And for the example with Invoice2Go, it was a feature called engage. And for many of our users that signed up to have an invoicing solution, if we now just said, here’s engage, it goes right over their head. It went over my head and I’m supposed to be the expert in the product, right? So what we did was we converted all the action statements into the direct


took that action. And we ran this newsletter, like the product piece section, with this approach a couple times. And every single time when we had a call to action product feature, the call to value version, like the variant B, would come back with statistically significant click-through rate and conversion rate every single time, which was really cool. So the newsletter in itself, the strategy for segmentation


maybe didn’t work out the way that we wanted it to, but there were so many other learnings where we did like many tests that had crossover effect. Yeah, that makes sense. And so with the call to value stuff, like you ran the A-B test and then after, you know, if it was like consistently coming back as the right way to go, did you eventually stop the A-B test and just like do the call to value all the time? Yeah, I like to run a test a couple of times because I always get nervous that it’s a fluke or like.


And I mean, I’ve had some people like argue with me, like, if you want to test once and it comes back statistically significant, why is it not statistically significant? I would look at statistical significant results in an automation and be like, this had data over a period of time with audiences that may have had, you know, weird external factor things that have impacted them, but it’s statistically significant.


I worry with one-off tests, it’s a fluke. So I like to run it like three times. Yeah. It could have just been like the copy in the call to value. Completely. You said it was like better that week or the design was better that week or, you know, whatever, right? Yeah. I like to like be able to say when we went hard on this call to value approach multiple times and invested in converting all of these action based statements into the value that someone gets.


And maybe it’s just like more critical thinking copywriting. I like to be able to look back on all of those and be like, this is the way we need to be thinking moving forward for everything. And we need to take these insights back into how we communicate new features inside the product with in-app messages and the onboarding emails. We should be more focused on how we communicate new things to our customers because just telling them to do something isn’t enough.


Cool. If there aren’t any other things, I’d like to quickly talk about your work at Later, because you also ran newsletters there. I don’t think we have super a lot of time, but it’d be really interesting to hear about that as well. Yeah. So I joined Later as their first in-house email marketing specialist, and they had a massive… I mean, it was a small company. I think I was employing maybe number 96, but they had a large brand team.


that had what felt like nine to 10 people on it, focused on this newsletter that they would send on Mondays and Thursdays to an audience of three million. And they had, over their period of successful time, they had grown this list just due to creating really valuable content on social media strategy. And the tool and product itself kind of came like on the back burner.


Like people were aware of the later blog and they were aware of all this amazing strategy information but they didn’t necessarily know about the tool that was driving revenue for the business. And an email list of like 3 million people is not cheap. I mean we were using Mailchimp so it was probably like the cheapest but… Although Mailchimp’s gone up a lot recently. It has, yeah, yeah. So maybe it wouldn’t be cheap in today’s time but I came in…


on the growth team and my job was to basically convert leads into subscribers. And they had already built out kind of onboarding or customer success team that owned the communication touch points once someone had paid or like signed up to a subscription. So my whole job was really to come in and disturb this newsletter and try and get as many leads out of it as possible. And I think


You know, the key points that I saw and then immediately changed were we did a lot of list hygiene right away. I think, you know, a three million number is amazing. Like that is phenomenal growth from the blog and it’s an amazing metric to tout, to say like we have this many people that have been interested in our blog and like signed up to hear from us.


But over five years of running the same newsletter, people switched jobs, they’re not interested. Their emails are not necessarily bouncing, but it’s like, I’ve left the company for further inquiries. Please, please reach out to So-and-So. And there was so many things like that happening. So I think I immediately called down the list to 800,000. It was like, here is 800,000 people that have.


either signed up in the past six months or clicked on something or opened something in the past six months. That was when opens were more reliable. And it was great. Like it was still a very healthy, we still had the same amount of people clicking through every week. Like those metrics didn’t drop even though the list size dropped. But for me with my job, now trying to convert people and drive revenue, I had a healthier list to work with. And I could.


better set expectations for actually how many people I was working with. Because to say, yeah, I’ve got 3 million people, 3 million leads to work with, that wasn’t the case. So many people were unengaged. But yeah, that was kind of my initial kind of challenge starting the role. And then so how did you turn those 800,000 engaged subscribers into paying customers?


our free customers? I mean, that was what I tried to do. Yeah. So through a lot of lead nurturers, when I joined, they had kind of individual nurturers going for every signup form on the blog. And I think they had like, 84 different signup forms across the blog. For like every blog article that was driving high amounts of traffic, there was like an embedded signup form in there.


And then when someone signed up, they would get like a source of hack the algorithm or whatever. And then that would have its own individual journey inside of MailChimp. And my first thing was to look at all of those. And I looked at them and they were all like content marketing funnels. So instead of talking about Later as a social media scheduling tool, they were talking about


other ways to hack the algorithm or like other ways to get your social media content visible on Instagram. And so I went in and I audited a lot of them to shout out about the product in line with where they came from to still maintain that level of personalization but they needed more product visibility and same with the newsletter too like we needed a product section in that newsletter there was no mention of signing up to later in there.


So I think that was the first thing that I pushed on was there has to be some sort of call to action. Like we’re bleeding, we’re bleeding sends if we don’t mention the product in our own newsletter, you know, even if it drives like five to 10 subscribers out of the 800,000, like that’s a win. But without mention of the product, there’s no one. So yeah. Yeah, that’s such a good point. What’s one…


key learning that you had from your time at Later? I think to continually highlight why certain changes are going to positively impact the business. I think some of the challenges I faced there were people feeling really attached to this newsletter program that was built over a five-year period, which they have every right to feel attached to it because growing a newsletter less to three million is a huge accomplishment.


But when that growth piece comes in and the business changes in scales, I needed to be better at making an argument for why those changes were necessary. And it sometimes felt like people were like, I don’t understand why we need to do this. And what I realize now, looking back, is I should have been more prepared to say, we’re going to drive 10 times more revenue from this newsletter. And


It’s great to say that we’ve built it to three million, but what if we can also attach a revenue value to it, to say to the C-suite, like, look at what we’re doing with this great content marketing that’s grown over five years. So yeah, always tie things back to the business value. And I think the other thing that I came out of it was, like, processes and documentation on best practices are invaluable. Yeah. I feel like…


always tying things back to business value and monetization is just like the, you know, mic drop. Like there’s no other argument aside from that, right? Yeah. It’s the strongest thing that you can say. It’s funny because I’m now in the role at Parcel where I’m trying to build the community aspect to it. And if someone were to say to me today, like, how many subscribers are you getting from the weekly newsletter? I’d be like, I don’t know. Like I do know I could pull the numbers, but it’s just a different…


a different part of the growth lifecycle, I think, depending on the audience size too, right? Like in the early days, I think you absolutely need to focus on this growth and building that strong foundation so that those people can promote you and you can grow your audience that way. But at some point you should look at it and say, what can we do better so that we as a company or we as a brand benefit from this? Yeah, that’s for sure. It’s always kind of like a…


It’s a balance, right? Like we go through this at Newsletter Glue as well. Like, do we monetize our small list or do we try to grow a bit and like, you know, get more brand awareness out there? Because there’s both Parcel and us, like we’re small teams and we can’t do both. And sometimes also, if you do do both, you kind of prematurely use the social equity that you’ve built up in selling.


as compared to kind of like nurturing over a long period of time, so that when you do have a large enough list and you do sell, you know, the response is better. 100%. You know, there’s probably like, with every business where that line is drawn is different. Like if you had a newsletter to focus on Fortune 100 companies, or like the executives of Fortune 100 companies, like your list is never going to be that big, but it’s possible that your list of…


100 subscribers, you could start to monetize that once you hit 100 subscribers. In comparison, if you have a massive B2C tool later, trying to monetize a list of 100 subscribers would just be a horrible idea. And you have to kind of build to 3 million subscribers to get the value out of it. Yeah, and it’s kind of interesting trying to navigate that as you’re building the business because the line is not obvious.


so dependent on the niche, what you’re trying to do and yeah. I think with the monetization piece is there’s such a worry that the newsletter will lose its authenticity if you go down the monetization route, right? And I think there’s a delicate line that can be walked where you say, okay, we need to bring in we need to bring in the big guns to monetize this and to get business value out of it. But like, why did these people originally sign up to us? And like, how


we’re still this amazing thing that we have created over the years or months or days. Yeah, it’s a hard one. Well, I guess we will keep chipping away at the problem. Yep. So we’re going to go into a section called Quick Wrecks, where I ask for your recommendations in the email newsletter world, I guess. Oh, fun! So the first question is, what’s an underrated ESP that you wish people talked about more and why?


I mean, I got to say, right? I got to say it. I do believe, I do strongly believe. Are they underrated? Sometimes I feel like no one’s ever heard of them. And I’m like, their automation journey builder is phenomenal. And no one is talking about it. I want people to be yelling about it, you know? There’s another really interesting ESP that I’ve just kind of started to track. EcoSend, I don’t know if you’ve heard of it. I think it’s called EcoSend. I haven’t heard of them. It’s like…


crafted on the basis of being eco-friendly, which is really cool. Interesting. And even like I’m an admin with the email markup consortium, so we talk a lot about email standardization and accessibility. And I think a really interesting topic of conversation that’s going to come up over the next couple of years is like, what is the ecological impact of sending email? And like, what’s the file?


If you knew that sending file sizes over a certain amount was going to cost more money, would you work on ensuring that your code was clean and all that stuff? I find that, I don’t know necessarily if it’s an underrated one, but maybe an undiscovered gem alongside customer. Yeah, I haven’t heard of Ecocent, so thanks. I’m glad you talked about it. And now me and more people can check it out. Okay, next question. What’s your favorite must-subscribe, must-read newsletter?


Um, the newsletters that I have on my like must subscribe list are Canadian specific. That’s okay. I have one individual, her name is Bridget Casey, and I actually discovered her on TikTok, which is funny how like the whole marketing thing is such an ecosystem. But I discovered her on TikTok and she was specifically giving out like Canadian financial knowledge. And then.


through one of her TikToks, she was like, I have a newsletter where I talk about latest changes in the Canadian financial market and how the stock market is. And just new accounts that are coming up that could be beneficial for first time home buyers and all that stuff. So I signed up and then she just sends like a great, I guess, plain text type email every week. It’s always super well written. And I ended up converting and I bought a course from her and I like loved the course. So.


It’s funny when you do find those like niche newsletters where I’m like, where was I? Like I didn’t know this existed six months ago. And now I’m like, every time it’s in my inbox, I’m like, I have to read it. So there’s that one and then Wealthsimple, which is also a Canadian company. They have a Monday newsletter called TLDR, where they go over just latest information in the financial market. And it’s an easy read and it’s one I see every week in my inbox. And I’m like excited to sit down.


and read it, which is cool. Nice. And last question, what’s your favourite piece of advice for newsletter publishers? I think maybe just don’t be afraid to test things out. I think that’s really the only way that you’ll spark growth and see what works and doesn’t work. I think, you know, when you start with email and you’re maybe brand new to the email world, you might…


find a template and think you have to work within the bounds of what’s provided to you, whether it’s like copy length or header or CTA button. And I think the newsletters that have stood out to me the most are ones that do not take the traditional like templated approach. So just yeah, the inbox is, you know, flooded with people and businesses and brands these days. So it’s worth it to test things and see if they work better for.


for you and your audience. And the other thing is I do not believe in benchmarks. I constantly see people be like, what’s the benchmark open rate? And I’m like, for what? Like, are you retail? Are you insurance? How many subscribers do you have? When was the last time you cleaned your list? Like, I do not trust benchmarks. I think everyone should create their own and try and improve their own from whatever they have in front of them. That’s such good advice.


And on that note, thanks so much for coming on the show. Thank you so much for having me. It’s been awesome to have you. This was a blast. I love talking about email. Yay. If people want to learn more about you and where to find you, where can they go? I am on Twitter. My handle is emailfromnaomi. And I also have that same handle on Instagram, emailfromnaomi. And then I also have a website,, which I have my very slow email listed in my folder. Thanks, Naomi.


Thank you, thank you so much.

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