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How to Play The Long Game with Life Cycle Marketing – Jess Chan, Longplay Brands

About the guests

Jess Chan

Kunle Campbell

Jess Chan is the Founder & CEO of Longplay, a full-service retention & lifecycle marketing agency for DTC e-commerce brands. Jess bootstrapped the agency - scaling to 7-figures in revenue in the first 18 months, and since then the business has continued to scale sustainably and profitably with a remote team. Longplay has generated $300M+ in email revenue working with clients from startup to $500M+.

On today’s episode, Kunle is joined by Jess Chan, Founder & CEO of Longplay Brands, a marketing agency that helps D2C brands nurture and retain customers through full-service retention and life cycle marketing.

Working her way up from being a marketing assistant to being the CMO of a multi-million dollar DTC eCommerce company, Jess Chan decided to build her own company, Longplay Brands after being sought after by different entrepreneurs with regard to marketing. She manages to live her core values and to turn out to be who she actually wants to be.

Longplay Brands, while being a young company, upholds their clients’ experience with their high quality and white-glove service and attained their first million dollar mark in their first eighteen months. That being said, Jess also opened up with her struggles in the company’s first two years. She shared how Longplay Brands maintains their client base and the company’s work culture and education.

This episode is especially inspiring as you’d hear Kunle and Jess talk about her journey from battling depression to being the successful CEO that she is. You will also learn about quality client and customer experience and the importance of knowing your target customers in marketing your product.

Here is a summary of some of the most important points made:

  • It is important to have the right growth plans for people and the right financial and legal systems in building stability for a company.
  • Scaling is important but Longplay focuses on finding higher-quality clients, thus, keeping their client count at around twenty.
  • Longplay sees SMS and email as channels for retention marketing.
  • “There is no one email that’s going to blow it all away. It’s about all of it working together.”
  • When making creatives, it should be both conversion-optimized and a branded approach.

Covered Topics:

On today’s interview, Kunle and Jess discuss:

  • Who is Jess Chan?
  • Jess’ Daily Habits and Life Perspectives
  • Jess’ Journey from Marketing Assistant to CEO
  • Longplay Brands’ Beginnings
  • Entrepreneurial Operating System (EOS)
  • Longplay Brands’ Scaling and Selectiveness in Clients
  • How D2C Brands Should Approach Life Cycle Marketing
  • Customer Segmentation Strategy
  • Quizzes in Lifecycle Marketing Strategy
  • Email Collection in 2022
  • North Star Metrics in Life Cycle Marketing
  • Benchmarking
  • Importance and Place of Creatives in the Lifecycle Marketing Strategy
  • Longplay Brands’ Strategy Mapping
  • Longplay Brands’ Team Members
  • SMS as a Critical Marketing Strategy
  • Social Media’s Role in D2C and Customer Relationship
  • 2020 vs 2022 eCommerce Marketing


  • 06:07 – Who is Jess Chan?
    • Founder and CEO of Longplay Brands, a full service retention life cycle marketing agency for D2C econ brands.
    • She has a background in actuarial science, economics and political science.
    • Jess worked as CMO at a D2C eComm company.
    • She went through a depressive period for a year and a half and read her way out of it.
  • 12:17 – Jess’ Daily Habits and Life Perspectives
    • “Instead of saying, ‘I want to be able to be on a beach and work a few hours,” it was more like, ‘I want to love what I do. I want to feel excited.’”
    • She created a morning routine.
  • 16:14 – Jess’ Journey from Marketing Assistant to CEO
    • Jess worked at BestSelf Co as a marketing assistant and also wanted to start her own thing.
    • She saw a future in the email and SMS channels and it requires many different skill sets more than content or influencer marketing.
    • “I learned everything I could at that stage of my journey and it was time to move on.”
  • 18:58 – Longplay’s Beginnings
    • It started around May 2019.
    • The first two years were “grueling”. They scaled their first million-dollar within the first 18 months.
    • Jess was burnt out because Longplay doesn’t have the infrastructure yet in terms of financial and legal systems.
    • “It was not set up to be sustainable in the sense that we didn’t have the right org chart structure. We didn’t have the right growth plans for people.”
    • COO and Longplay partner, Rachyl Neidecker forced Jess into the EOS model and taught her how important it is to operate.
  • 22:53 – Entrepreneurial Operating System (EOS)
    • “EOS model functions by having a visionary and integrator.”
    • The visionary is the CEO and/or founder and the COO is the integrator that runs the entirety of the business, and reports to the visionary.
    • “Visionaries don’t like management.”
    • “It is a true partnership. That’s probably one of the things I value most now in scaling Longplay.”
  • 26:57 – Longplay’s Scaling and Selectiveness in Clients
    • Longplay keeps their client count around twenty to make sure they deliver a more “personalized, white-glove” experience.
    • “We can focus on finding higher-quality clients and working with them on a deeper level.”
  • 29:39 – How D2C Brands’ Should Approach Life Cycle Marketing
    • Retention Life Cycle Marketing is about thinking holistically.
    • “There is no one email that’s going to blow it all away.”
  • 32:45 – Customer Segmentation Strategy
    • In terms of positioning, messaging and branding, Longplay uses the typical customer avatar approach.
    • “When it comes to segmentation and building on different customer journeys, we look at purchase behavior more.”
    • “We find that customers who would complete the quiz on-site to help them choose their supplements have a different buyer journey than someone who doesn’t.”
  • 36:10 – Quizzes in Lifecycle Marketing Strategy
    • Quizzes should not be in all life cycle marketing strategies as it really depends on the product.
    • “Quizzes are there to solve a problem. They’re there to solve the problem of choice fatigue.”
    • “Quizzes work well with companies with large catalogs where they’re all the same in a sense.” Examples are deodorants with different scents and apparels.
  • 38:26 – Email Collection in 2022
    • “One of the most important things I’d say for people to remember is you don’t need an email list. You need a list of potential customers.”
    • “Knowing your customer well and having the data is important.”
    • “When it comes to list growth, the foundational principle is, are these the lists for your potential customers?”
  • 41:26 – North Star Metrics in Life Cycle Marketing
    • Revenue, open rate, click rate and dollar per recipient.
    • Dollar per recipient isn’t used as much but it can still give you an idea if it is working or not.
  • 42:02 – Benchmarking
    • Longplay usually pays attention to industry benchmarks but it is not always helpful in decision-making.
    • “One of the principles in our approach to reporting is, it has to be actionable.”
    • Important metrics are the industry benchmarks, time between purchases, putting a timeframe on your lifetime value, and lapse rate.
    • Dollar-per-recipient and industry benchmark can be found in Klaviyo while lapse rate and six-month lifetime value are hard to find in it.
  • 45:14 – Importance and Place of Creatives in the Lifecycle Marketing Strategy
    • Longplay’s creative team, both copy and design, blends and develops techniques on the creative side.
    • The creatives are both conversion-optimized and aligned with the brand’s tone and voice.
    • “What is the strategic way to communicate this message through copy? What is the strategic way for a copy design to work together to communicate something in a different way?”
  • 48:56 – Longplay’s Strategy Mapping
    • Onboarding takes 4 to 6 weeks and is critical to the quality that they build.
    • They sit with founders or CEOs or whoever’s in-charge and ask questions about their customers, their approach to discounting.
    • “It’s our job to understand the business first for us to make those decisions and understand the customer first.”
  • 54:00 – Longplay Brand’s Team Members
    • Team training is more focused on “how to think” versus “how to do.”
    • “I find education to be important. Everything that we do has been built around, how do you educate from the ground up?”
    • “A lot of entrepreneurs found their initial success by being intuitive but intuitive is not scalable. It has to be built in a way that is a complete no-brainer. “
  • 57:39 – SMS as a Critical Marketing Strategy
    • “Every brand should try to do SMS.”
    • “When does it make sense to communicate this thing through email? When does it make sense to communicate this thing through SMS?”
    • Longplay Brands’ strategy still skews slightly towards email and then they send SMS as a follow-up.
  • 01:01:26 – Social Media’s Role in D2C and Customer Relationship
    • Social Media can be a little different in the sense that every channel can be effective for anyone but not for everyone.
    • The biggest issue that brands and entrepreneurs run into is the shiny object syndrome.
    • “A lot of channels can work if you do it properly but most people don’t have the resources to do it all properly. You need to pick and choose. “
  • 01:04:11 – 2020 vs 2022 eCommerce Marketing
    • “Acquisition and top-of-funnel are becoming more difficult and more expensive. Now’s the time to focus a little bit more on that retention lifecycle marketing side.”
    • “Focus on keeping your customers and building that loyalty.”


  • D2C brands should look at life cycle marketing holistically.
  • List growth strategy should bring you into contact with people who might buy your product.
  • Knowing your customer is first and foremost when it comes to retention marketing strategy.
  • “It’s balancing those two. Build your brand loyalty and double down on making sure you’re creating a great client and customer experience.”

Links & Resources:

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On this episode, we’re going to be talking about how to play the long game when it comes to lifecycle marketing, that’s email and SMS marketing. It’s a great episode you do not want to miss.

Welcome to the 2X eCommerce podcast show. This is the podcast dedicated to rapid growth in online retail. This episode is an interview I had with Jess Chan, she’s the Founder and CEO of Longplay, a full service retention and lifecycle marketing agency for direct-to-consumer eCommerce brands. Jess bootstrapped the agency scaling it to over $1 million in revenue in the first eighteen months.

Since then, the business has continued to scale and thrive sustainably and profitably. Longplay has generated over $300 million in email revenue working with clients from startups to $500 million-plus brands. This is a terrific episode I had with her, quality conversation. She talks about the entrepreneur operating system. This is about the 2nd or 3rd time I’m hearing about it. She sheds a bit more light on it over the conversation.

More importantly, she speaks to personalization, segmentation, your email marketing strategy, and how to look at it holistically and also from a long-term view. This is a terrific episode. I do not want to say much. She is a clever speaker. She’s going to be speaking at the Commerce Accel conference. If you haven’t already, go to CommerceAccel.com to get your tickets. This is a great episode. Enjoy this episode. I’ll catch you on the other side. Thank you for reading.

Jess, welcome to the 2X eCommerce podcast.

Thank you so much for having me. I’m excited to chat today.

I’ve been looking forward to this conversation. When the opportunity came to speak with you guys at Longplay, I was like, “Please, let’s go for it.” For the readers who don’t know who you are, Jess Chan, the CEO and Founder of Longplay Brands, could you take a minute to give us a brief introduction?

I am the Founder and CEO of Longplay brands. We are a full-service retention lifecycle marketing agency for direct-to-consumer eComm brands. We work with brands, manage all their email and SMS, and build out holistic customer journeys through email and SMS to nurture, convert, and retain their customers at each stage of that customer journey. I got my background in actuarial science and economics and then worked my way up into a CMO role at a D2C eComm company and then started Longplay from there. Longplay was honestly scratching my own itch of building the retention lifecycle marketing agency that I couldn’t find as a CMO.

That’s the intro to growing up, Jess Chan, who is the CEO, founder, and entrepreneur of quite a fast-growing retention agency. Should we go back to the child Jess? What was growing up like? How were your formative years to you being an entrepreneur now?

Honestly, childhood was amazing. I had the best parents that anyone could ask for. They did a good job of letting me explore my own interests, take responsibility for my own actions, and be responsible for trying the best I could. It’s one of those values that doesn’t come out until you’re tested in the entrepreneurship space.

I was lucky to have different mentors that found me at different stages of my life and one of the key ones was my high school teacher, Cody, who was a big part of expanding my worldview and teaching me that there’s so much more to life. Life is about your choices. You could choose anything. He broadened me up to realize that you don’t have to do the linear path. You don’t have to go to school and then graduate and do the job. You can take a year off. You can completely switch career paths. You can change your mind at any given point. You are only responsible for your choices and you always get to choose. That was a powerful lesson to learn early on.

At that time, even though there wasn’t necessarily a major life switch I wanted to make, that idea planted the seed in me that allowed me to have the courage to jumpstart my entrepreneurship journey. The big catalyst of when the journey began was when I did my degree in actuarial science, economics, and political science in school as far from business marketing as possible. I was on that path for a little while. It felt like the logical choice and I was good at it. I was good at math and economics. I could do it but something didn’t feel right for me.

In the 2nd and 3rd years, I went through a depressive episode. It was a year and a half of dark crap, quite frankly, suicidal thoughts, panic attacks constantly, feeling trapped and overwhelmed at the same time, and not seeing a way out. The entry into the self-development space was my way of pulling myself out of that. In my childhood, whenever anything went wrong, I would read something. I was like, “I don’t feel great. I’m going to read.”

I started going online and found all of these niche blogs. There’s Live Your Legend, which is still going on, Cal Newport, Seth Godin, and all those self-development books that are so popular now. I went down that path and pulled myself out with all these daily routines. I was like, “As long as I run three hours a day, listen to a Tim Ferriss podcast, write a blog post, and do my studies, at least I can keep being sane.” That was my entryway into everything.

When I started pulling myself up, it was a catalyst for me to explore, “Now that I can breathe again, what do I want to do?” That was when I ended up applying for a job as a marketing assistant at a company called BestSelf Co and worked with them part-time in my last years of college. When I graduated, I became the Chief Marketing Officer. I was working with them for three years. Amazing team, amazing company, and amazing products. It was one of the happiest periods in my life and a fulfilling period of my life. I then went to start a Longplay almost accidentally as things took off.

There’s a lot to pick from your initial story. Given the fact that, in college, you had that breakdown and you read your way pretty much out of a rut is something to reflect on and uphold. Speaking of BestSelf Co, it was season four, we had Allen Brouwer from BestSelf Co. We recorded two hours of an episode. We had split it out into two episodes. You sounded like you were building something quite substantial to know your part of it. It’s super interesting in itself. What daily habits did you adopt that formulated or changed the way you started to view perspectives and life in general and know, “Entrepreneurship is probably going to be that route I will take.”

I’m going to answer it slightly differently in the sense that ideas powered me during that time and also daily routines. One of the core ideas was the idea that I could rebuild myself and reconstruct everything because I felt trapped. I felt like I didn’t know who I was or where I was going. I felt this total disintegration of like, “Who am I? What do I want to do? I don’t know what’s going on.” Especially with suicidal thoughts and panic attacks, if anyone’s been through it, it’s almost like this reality distortion field that happens.

One of the core ideas there was this idea, “If I don’t like what I have in my life, I don’t like where I’m going, and I don’t know if I like who I am specifically, or I don’t know if I’m fully expressed as a person, let me build it all from scratch. What do I want my life to look like? Who do I want to be? What do I want my personality to be like? What do I care about as a person? What do I want to be acting out of? What am I choosing? What are my core values?” That was probably one of the core ideas that powered everything.

From there, it became, “Great. If I can rebuild everything from scratch and if I can rebuild who I am, my identity, and my life path, what do I want to build?” That was the catalyst to start reading my way out of the problem. It was like, “Let me turn out who I want to be. Let’s read some self-development books. What types of people do I look up to? What kind of person do I want to be? How do we decide what kind of person we want to be?” That’s when I read a lot of history and read a lot of self-development books.

When it came to, what kind of life do I want to build? That’s when Tim Ferriss, The 4-Hour Workweek, and all of those entrepreneurship lifestyle guides came up. One of the biggest differences for me was about, “How do I want to feel and how do I want to act?” Instead of saying, “I want to be able to be on a beach and I want to work a few hours.” It was more like, “I want to love what I do. I want to feel excited.” For me, it was important that I want to wake up excited every day. I was like, “If I can wake up excited every day, that to me is already such a great life.” You can be excited about so many things and things can be challenging but if you’re excited about them, it’s right.

I created these core pillars for solving that problem of what I want to build. From there, a lot of morning routine. For a while, I woke up at 6:00 AM. I would read for an hour or two hours in the morning, that was super critical to me. After an hour or two hours, I’d be excited to go to work or excited to do whatever I need to do next. I did a lot of time blocking to honestly distract my mind because my mind was going off to these dark places. It was like, “No time to think. It is 10:00 AM and it’s time to write your blog post of the day. You will then eat lunch and then you will study for two hours and then you have class.” This was also during school. The routine was important for me, for sure.

Looking at what you want to be and then trying to align with the people that you want to be and stick into too routine. Longplay, when did you start? What’s been your journey thus far? You’re full-service retention and lifecycle marketing partner, which we love. You’re thinking long-term. We like the play there, Longplay. Retention is what grows eCommerce brands. What’s been the journey? You started out phenomenally. You started as a marketing assistant at BestSelf CO. You finish that off with a CMO role heading all their marketing and then you moved on to Longplay. What’s been the journey thus far?

I loved it at BestSelf. I had no intention to leave at any point. I knew I wanted to start my own thing at some point but I also loved it there. I was attending different entrepreneurship events and conferences and meeting people there. I would share what I was doing naturally on the retention lifecycle marketing side and email side with BestSelf because I was already flexing my muscles a little bit there and love the channel. Eventually, other entrepreneurs would say, “Can I hire you? Can you consult? Can you do this?”

At first, I was dabbling and someone would be like, “Can you help me with content marketing?” I’m like, “Sure, I’ll help you with that.” I said yes to everything and then eventually narrowed it down to email and SMS because I saw a future in those channels. It felt like the right model and also, it was difficult to get into. It’s a little bit easier to go into content marketing or influencer marketing but email and SMS flexed many different skillsets. I thought it was my unique edge to venture into that. That was how it started.

It got to a point where I was already hiring VAs to help with some of the backend stuff. I was working as efficiently as possible but there was one Black Friday, Cyber Monday, or Q4 period where I was running all of the BFCM Q4 stuff for BestSelf and managing the team there. I was also personally running it for 3 or 4 other brands and I was writing all of the emails and doing all of it.

I was like, “This is as efficient as I can possibly get. There’s no more efficiency to be squeezed out from me, personally.” That was more of like a catalyst of like, “There’s something here.” At that point, I wasn’t actively looking for clients. People were coming in. Eventually, I reached that point of, “I got to choose.” I wasn’t able to balance both and do both justly. I loved my time at BestSelf. Also, for me, I learned everything I could at that stage of my journey and it was time to move on.

I could rebuild myself and reconstruct everything. Click to Tweet

You need to learn the ropes and then get on your two feet and eventually span your wings and fly, which is what you did. What’s the situation now at Longplay? How many clients do you have? How have you built it? You started in 2020. Was that in the pandemic? What was the first year like and what is it like now? Please break the journey down.

We got our start probably around May 2019. The start date is a little bit fuzzy because of the journey. When did it start and stop? Around May 2019 is probably when we got our start. Honestly, the first year or two years were grueling. It took a piece of me. It takes your heart and soul to tend to this business. After that whole process, especially with entrepreneurship culture being popular these days, I’m the first one to say don’t start a business unless you can’t not start a business that it hits something inside you that you have to do.

It is not sitting on a beach and working remotely. I had a lot of great times like that where it looked picturesque but also so many nightmares and many things that come up. It was not easy. Within that first eighteen months, we had our first $1 million year, the first full year in business. It was cool but it was also so hard. It was what I call a castle built on sand. It was $1 million but it was not sustainable. Not because we didn’t have product market fit and not because we didn’t have a good business or it was flashy but because we didn’t have the infrastructure for it. I was burnt out.

People infrastructure or systems?

I’d say a little bit of both. We were already doing a lot of systems-based stuff. We had SOPs. We had a lot of delegation. I wasn’t doing everything myself but we didn’t have the infrastructure for it. It was good payroll systems, basic accounts receivable, and cashflow management. A basic org chart and team structures because it was flat.

Everyone was reporting to me but I hate management. I don’t want to be accountable for other people. I can be accountable for myself. Once I give you the vision and give you the instructions, I am pretty much done with the problem. It was not set up to be sustainable in the sense that we didn’t have the right org chart structure. We didn’t have the right growth plans for people. I want to invest in people but I was burnt out. Also, I’m not a manager.

We didn’t have the right financial systems, the right legal systems to cover our bases. With that, missing some of these core systems to scale, which is less so about individual SOPs. It’s more about, how do you integrate and onboard people? How do you make sure those SOPs are executed on? That’s where my COO and also a partner at Longplay, Rachyl Neidecker, was critical to getting past that first $1 million.

The first $1 million was an achievement but getting past that was probably even the harder part, believe it or not. It was about stabilizing. We spent so much time on foundation building. She was the one who forced me into this EOS model in the most beautiful and loving way because I was so resistant. I was kicking and screaming. With the EOS model, she taught me how important to operate.

You’ve got to break the EOS model for people who don’t know what it is. It’s the Entrepreneurial Operating System.

Honestly, I’m not going to pretend to be an expert on this. You should have Rachyl on the podcast at some point as well. The EOS model functions by having a visionary and integrator. That’s going to be your CEO, your founder, and then also your CEO as well. The COO or integrator is the only person that reports to the visionary because visionaries don’t like management. The COO runs the entirety of the business. It is a true partnership. That’s probably one of the things I value most now in scaling Longplay.

I did the first $1 million alone and I needed to do it alone for personal reasons. Now, I get to do the next $10 million and $20 million. It takes a partnership. It takes someone who is world-class at operations. Rachyl is the best COO I’ve ever met. It’s hard to find people who are not only world-class at what they do but also understand business. Entrepreneurs, we’re a finicky bunch.

This tells me two things. First, you guys have a unique approach to your product. The way you execute lifecycle marketing is unique to your company, probably proprietary. The second is you’re selective with the clients you take in order for you to deliver and maintain the staying power. What you’re doing is down to retention. It’s about keeping the customer and not acquiring. It’s so much work trying to onboard a new client. Where are you guys from a client base? How many clients are you serving? Are you geographically agnostic? Are you platform agnostic from an ESP standpoint? I’d like to find out more, please.

We keep our client count roughly around the twenty-client mark. We do have plans to continue scaling that but we’ve always been pretty adamant that we’re not the agency that we want to start merging with other agencies, getting a client roster of 150 clients, and all that. Inevitably, the quality goes down. Instead, we can focus on finding higher-quality clients and working with them on a deeper level. We’re starting a software company as well as our growth strategy. We stay around 15 to 20, usually 20, client mark, and deliver that personalized white glove experience.

From an industry standpoint, we exclusively work with D2C eComm clients but they’re usually all over the place, apparel, fashion, beauty supplements, and home goods. We’ve worked with companies serving car owners as well. Most of our clients are on Shopify, somewhere on WooCommerce or BigCommerce.

All of our clients would go over to Klaviyo. We do have clients we start elsewhere on our outdated ESPs. We exclusively work on Klaviyo because they do genuinely have the best platform for D2C eComm businesses who want to focus on retention like marketing because you need that data. You need that to be able to leverage all that data. That’s the difference. That’s usually where we operate.

We always hear good things about Klaviyo. We use Klaviyo ourselves. They’re sponsors of this podcast. In terms of your approach, from a first principles perspective, how should D2C brands approach lifecycle marketing in today’s world of email and SMS?

The approach is to look at it holistically. I find that a lot of clients or brands that I speak to try to apply top-of-funnel and ads marketing strategies to retention lifecycle marketing. In the world of ads, you’re always looking for that next ad that’s going to go viral or that next Facebook ad that’s going to have that 10X ads. It’s like placing bets.

Each ad is separate from each other. It’s about disrupting yourself. On the retention lifecycle marketing side, it’s about thinking holistically. There’s no one email that’s going to blow it all away. It’s about all of it working together. It’s not about what’s the one ad that’s going to catch your eye. It’s about, what do you want to talk to the customer about for six months?

When we look at customer lifecycle journeys, when we onboard new clients, we always talk about timeframes. In 6 months, 12 months, or 2 years, what’s your ideal customer journey? How do you want them to interact with your brand? What do you want them to think of first? What do you want them to shop first? How often are they going to come back ideally? What are their purchase patterns? What’s their mindset?

We rarely started the conversation with, “What email strategy would you like to try? What ideas have you had? What has worked well in the past?” One, we can always look that stuff up. Two, that’s the wrong way to think about it. Probably the biggest shift that brands need to make when they’re focused on retention lifecycle marketing is it’s not going to be the one explosive thing that’s going to 10X your revenue in two months.

If any email agency is sitting there saying, “We’re going to 10X your revenue in 60 days.” They can and we can do that too but it’s going to be at the cost of burning out your list because the back end and the front end don’t operate the same way. You can have the one Facebook ad that changes your business in a real way. That’s not the way email is going to work because you’re burning up the trust of your customers.

You’re thinking about the customer first and you’re thinking about that long-term conversation you’re going to have with the clients over 6  months, 9 months, or even 1 year. You’re nurturing a relationship, which probably takes us to the topic of segmentation. How do best-in-class eCommerce businesses segment customers?

You do have those winner Facebook ads that get those impulse purchases. A lot of the leads or sales do slip through the cracks and never come to fruition. I’m not an expert in this but what a lot of brands may be missing might be an effective segmentation strategy. What is your approach to segmentation? How are you viewing customers in order to speak to them effectively?

When it comes to customer segmentation, there are two camps that people take there. One is the typical customer avatar approach. We still use the avatar approach in terms of positioning, messaging, and branding. When it comes to segmentation and building on different customer journeys, we look at purchase behavior more. We’ll look at what is the first purchase that someone made and does that indicate what their next few purchases are going to look like.

Theoretically, you have health and wellness companies selling supplements and you have a group of supplements that help with bloating and you have a group of supplements to help with fatigue and one with sleep. We can talk about the customer who is in LA and makes this much money and drives his car but that’s not useful. What’s useful is, did the person come in for bloating, sleep, or fatigue? What did they buy first? What content did they read? That’s where what ad they came in helps. Whatever they clicked on, whatever caught their eye gives you an indication of what their pain point might be.

We find that customers who would complete the quiz on-site to help them choose their supplements have a different buyer journey than someone who doesn’t. Let’s segment the customers. For customers who complete the quiz, these are our next goals for them. If they complete the quiz, we want to make sure they buy the product that’s recommended.

We want to follow up with a lot of content because they seem to care about something that’s personalized. We’re going to give them personal content to continue the conversation on what they found out with the quiz. If people don’t complete the quiz, we’re going to first try to get them to complete the quiz. If not, maybe we will try to give them this starter product that’s the cheapest as a quick fix for whatever their key issue is.

Whenever we talk about customer lifecycle mapping, it becomes this tree with different branches. What are the 3 or 4 key actions that customers take when they come to your site? It’s probably some combination of them taking a quiz, adding something to the cart, and don’t do anything or browsing. From those four different starting points, what are the next 2 or 3 things that you want them to do? Each action they take opens up 2 or 3 other pathways that they could take as well. All of our segmentation is usually based on customer behavior, whether it is purchase patterns or also what they don’t do.

I like the saying, “You judge people by what they do and what they say.” You’re taking what exactly they do and where can we take them next. You’re almost a chauffeur guided via email and SMS. Speaking of which, you spoke to quizzes. Should quizzes be in all lifecycle marketing strategies?

I’d say no because it depends on your product. There was a period when quizzes were popular back in 2018. Everyone is like, “Quizzes work. It goes on your site.” At the end of the day, it comes back to what’s the customer mindset? What’s the customer experience? What’s the customer journey? Quizzes are there to solve a problem. They’re there to solve the problem of choice fatigue. They’re like, “I don’t know what to do. I don’t know which one to choose. I don’t know where to start.” “You don’t have to decide anything. Take this quiz and answer these questions.”

The only time it makes sense to take quizzes is, quite frankly, if you have anything to deliver of value with a quiz. Sometimes it’s that customers can’t decide and it’s one method of deciding. With quizzes, they work well with companies with large product catalogs where they’re all the same in a sense that if you sell deodorant, it’s all the same deodorant but just different scents. Someone doesn’t know what to choose. It’s like, “That’s a good one.” It’s like, “That’s all the same. Here’s a quick quiz. Figure out which one’s your personality type or which one suits you.”

Apparel, the same thing. All t-shirts are the same. Nudge them in some direction or it is problems that solve a specific pain point like supplement companies. They are trying to find the right product to solve their problem. In those cases, quizzes make sense. If you have three products, you probably don’t need a quiz unless it’s hard to decide for whatever reason. I do find quizzes sometimes overused for the sake of it.

What’s your take on email collection in 2022? What is the best way to identify cold traffic via email in terms of email capture?

With email capture, it’s email list growth. One of the most important things I’d say for people to remember is you don’t need an email list. You need a list of potential customers. People get that mixed up quickly. They talk about building an email list and now they talk about buying an email list. What if you want a giveaway? All the strategies could be legitimate but they’re only legitimate if you feel like that group of people that’s going to come into that method might end up buying your product.

You can be excited about so many things and things can be challenging but if you're excited about them, it's right. Click to Tweet

If you sell supplements and give away an iPad, you’re not going to get a list of potential customers. You’re getting a list of people who want the chance to win an iPad. If you’re giving a giveaway with a list of supplements that are similar to what you do or giving away your own supplements, maybe. You might have some crossover there or you still might end up with a list of people who want free stuff.

When you’re doing list growth, does your list growth strategy bring you into contact with people who might buy your product? That’s where knowing your customer well and having some of that data is important. Also, on the side, make sure you’re segmenting those people separately. We have clients come in and they’re like, “I bought a list.” They would merge the list with their legitimate customers and now you have a hodgepodge of people. Keep it separate. If it’s bad, you can sequester them away. No damage has been done.

When it comes to list growth, the foundational principle is, are these the lists for your potential customers? What are some incentives that you can give them that will at least get them in the door and get them on your email list? It could be 10% or 15% off your store. That’s an effective strategy. Email lists capture is pretty straightforward at this point. Customers are savvier these days. They expect 10% or 15% Off. It always still continues working.

I’ve also seen successful list growth strategies with partnerships or with lead gen content and things like that. From a strategy standpoint, I don’t think the innovation is in, what’s this new hack, new giveaway, or new channel? Everyone has so much data these days on their customers. It’s about leaning into that more. Understand what your customers want to learn from you. What do customers want to hear from you? Turn that into a lead capture mechanism whether it’s content, PDFs, partnerships, or a simple discount on that email capture.

What are your north star metrics in lifecycle marketing?

There’s the usual like revenue, open rate, click rate, and purchase rate but most people already have those on the top of their list. Dollar per recipient is one that isn’t used as much but I find it a good apples-to-apples metric. If you have a dollar per recipient, you can ignore the open click rate and purchase rate to an extent and it gives you that quick, “Is this working or not working?”

Would you benchmark it against other companies in your vertical? Would you benchmark it against a general expectation?

With our benchmarking, we pay attention to industry benchmarks but we found that they’re not very helpful in deciding what to do. One of the principles in our approach to reporting is it has to be actionable. If I tell you that a company has a 30% open rate, that doesn’t mean anything. Is it good? Is that bad? We benchmark off of the company’s performance over the last six months to say, “Was this campaign good or bad? Is it trending upwards or is it trending downward?”

Some clients come in and like are like, “We’ve been working with them for two years.” We’re already far above industry benchmarks. If we looked at industry benchmarks, it’s like, “We’re above it. We’re doing great.” There’s still so much growth opportunity. That’s not very helpful. Some clients come in and they’re far below industry benchmarks, it’s like, “You’re off. We already knew that. You’re going to be continued to be off for months as it’s trending upwards.” That’s not actionable either.

The industry benchmark is good to know once and then you’d only do much off of it. It’s more of a fun fact than anything else. They are useful for people who aren’t specialized in email because you need something to gauge off of. We look at this stuff every day. To answer your earlier question, two other important metrics are the time between purchases. A lot of clients talk about wanting repeat purchases but if you have a high repeat purchase rate but it takes you ten years to get that second purchase, what good is that? The time between purchases and shortening that and getting that cashflow in the door is important.

The third one is putting a timeframe on your lifetime value. People talk about like lifetime value. If takes you 100 years to get your lifetime value, what good is that? You’re going to go out of business. We usually use a six-month lifetime value as a benchmark timeframe so you have something to gauge off of. The last one is the lapse rate. The lapse rate is applicable for software companies but I do think it’s applicable for eComm companies. If someone has bought from you and doesn’t buy again within 90 days, they’re probably never going to buy from you again. That means 90 days is your lapse rate and that helps you set timeframes on when you need to start to win back people.

Can you get all these metrics from Klaviyo?

The lapse rate is a little bit tougher. Six-month lifetime value is also tougher. The dollar per recipient is in Klaviyo. The industry benchmark is also in Klaviyo. At the end of the day, lapse rate and six-month lifetime value are hard to find on Klaviyo mainly because they are not email metrics. They’re retention and lifecycle marketing metrics. You’re going to find those in whatever dashboards you’re using for more lifecycle data.

Triple Whale should be able to deliver.

Triple Whale is fantastic.

What’s the importance of design? The two things I’ve picked up coming to your website is your focus on strategy and then your creatives. There are some nice-looking mobile-first templates. Typically, people would display what it looks like on a desktop. You guys have been intentional here on mobile. Do you want to speak to the importance and the place of creatives in the lifecycle marketing strategy?

Our creative team, both copy and design, is phenomenal. They’ve done a good job at finding that blend and developing techniques and strategies on the creative side to make sure it’s both conversion-optimized and also aligned with the brand tone and voice. I find that most brands choose one or the other. That’s where you hear a lot of debate about plain text or not. How aggressive should you have these banners? Should we have a big red flashing button? All that direct response type approach.

Also, you have the branded approach. Our team has done such an amazing job at blending the two. Their first thought is it’s not an either-or, it’s an and. We approach email design similar to website optimization or CRO design. You need to be branded. You need to be aligned. Also, let’s test what’s going to be optimized. They have their own principles around basic things, “Let’s make sure there’s a call to action above the fold. Let’s make sure this is readable if you’re going to quickly scroll through it.”

It’s putting yourself in the customer’s shoes and thinking, “If this person is in line for coffee, checking their email, which is probably what most people are doing.” No one’s sitting there on the phone, “I’m going to check my email and read this thing like a blog post today.” People are usually doing this between errands.

You only have three seconds to be eye-catching. You also still want to be branded as well. It’s putting yourself in the customer’s shoes. That’s where the creativity comes in. At the end day, it’s the materialization of strategy. We put so much work into what the customer needs to hear, when they need to hear it, what they need to hear, what point of the customer lifecycle they’re in, and what’s their customer journey? Where are they at, mindset-wise?

Now you have the creatives. They have the toughest job, which is how do you bring all that strategy together in a way that is interesting, in a way that’s unique, and in a way that the customer is like, “This thing caught my eye. This thing resonates with me.” When we talk about creative internally, strategy is part of that. There’s a creative strategy around, what is the strategic way to communicate this message through copy? What is the strategic way for a copy design to work together to communicate something in a different way?

I was going to ask if your copywriters and designers sit in the same room but you answered that question already.

It’s tough. We’re a fully remote team. That’s where collaboration is always a little bit tough. We still have the copy start the process but it is a collaborative thing along the way as well.

Speaking of strategy, which is always step one, you’re mapping out what they’ve done. Were they in the customer journey? Have they purchased one item or have they not purchased? What is the next step going to look like? That’s strategy mapping. How long does it take you to map out a strategy? Do you sit down with the founders or the operational team to understand their offering so you can map those journeys out? I would assume that strategy is your first step. What does the lifecycle marketing strategy look like?

Our onboarding period is between 4 to 6 weeks and that is one of those non-negotiables for us because it’s critical to the quality of what we build. It’s that onboarding period where we’re able to download all of the strategic thinking. We sit down with the founders, the CEOs, or whoever’s in charge of this portion of the business and we first have a strategy call. It’s usually an hour and a half. We’re downloading everything from them.

We’ll ask questions such as, what are the key things that you’ve seen that customers who’ve never bought from you before need to know about your brand or your products to make that decision? What are common products that if they can try these 2 or 3 products from you, they get bought into what you guys sell? From there, they usually become raving fans or at least have a higher likelihood of repeat purchases.

We’ll talk about your approach to discounting as a brand. What are your margins? Do you like discounting? What types of discounts have you run? When do you like to do discounting? Some brands want to do it once a month as a flash sale. Some brands avoid it completely. Those are a few example questions to give you an idea of how people should be thinking about doing email and SMS. We don’t ask things like, “How many emails do you want to send per month? Which customers do you want to send to?”

It’s our job to understand the business first for us to make those decisions and understand the customer first. We start at a high level and that’s why we say we do retention lifecycle marketing because we don’t ask email questions. We ask business questions. We start with that and then we also do a similar call on the creative side, more so understanding what resonates with the customers, their mindset, your tone of voice, and the brand of your business.

We spend the entire time doing a pretty deep download. From there, we do a strategy roadmap. That’s where we present a 3 to 6-month strategy. That gets in-depth around, what types of flows we want to build. What are your key business goals and how are we executing those goals? Through flows and campaigns. We’ll walk through AV tests we want to run as well. We also build an in-depth flow map. With some of our long-term clients, we built out flow maps for a six-month customer lifecycle journey. You have every single email that they’re going to get in a flow setting for six months and all those emails are built and timed to what your goals need to be.

At the three-month mark, they churn. At the six-month mark, if they haven’t churned, we want them to buy an XYZ product. This month, we want them to do XYZ. We then structure the entire journey. That’s how the strategy is executed. From there, we do the usual, build a brief and pass it over to creative. They understand what portion of the customer journey they’re writing for and they also understand the vision for the email and then it’s their job to execute that.

When you talk about six months ahead of a flow map stretching out to six months, you’re talking about persuasion. It’s an art of soft persuasion based on action. It’s phenomenal. I can’t imagine the tree structure, the branches you have based on certain actions and certain triggers over a six month period. I don’t want to see that tree. It would intimidate me.

I’m a nerd. I’m like, “This is the most beautiful thing on Earth.”

You probably start to draw symmetric parallels and all of that stuff. This probably brings me to the fact that your actuarial science background and analytical background are allowing develop these sophisticated flows. How do you export that to team members? That’s what companies are all about. For the strategy team members, are they analytical personality types?

That’s where systems come in. There are two pieces to that. One is a lot of our team training is on how to think versus how to do. A lot of our training or onboarding is built off of, here are the principles that we’re operating off of. Here’s what customer lifecycle marketing means to us. Here’s our approach to AB testing. Here’s our approach to deciding what success looks like. We see the role of email in the broader scheme of the business. A lot of our training is foundation driven.

One of the things that’s important for me is, eventually, to start a nonprofit in the education space. I hate the word passionate but I’ve been trying to avoid it. I find education to be important. Everything that we do has been built around, how do you educate from the ground up? That’s where having a great COO and operations team is important. Our operations team is world-class. Our HR director is amazing. They do a great job of funneling everything into my brain that is not very good for training and not good for a broad understanding and building it into bite-sized onboarding materials.

At the end of the day, it comes back to what's the customer mindset? What's the customer experience? What's the customer journey? Click to Tweet

To answer your question, it’s having an operations team partner with me to say, “Here’s how I think about this. Here’s everything in my brain. Here’s my approach.” They’re like, “That is not understandable. Can you describe it in a different way?” “This needs to get broken into a three-week course. You can’t teach that until six months in because they need to know all these other things first.” These are all the things that would come up to me. The first answer is finding someone who can download it out of your brain. Entrepreneurs are usually not good trainers. They have different skillsets.

The other thing is building systems around it. We have a lot of systems for even our analytics. We have systems around when to flag metrics are notable and starting to codify the thinking process and spend time saying, “I decided to do it this way for these reasons. What are the three things that you saw?” A lot of entrepreneurs found their initial success by being intuitive but intuitive is not scalable. It has to be built in a way that is a complete no-brainer.

All the systems we build are built assuming someone knows nothing about email coming in as a strategist. We hire a strategist who knows email already. We build it as if this person doesn’t know email or doesn’t know anything and has no experience in the space. How would you explain it to them? Bring in highly talented experienced people to work off of those systems but then they have the space to flex their creativity versus having to worry about doing everything your way. It’s been an iterative process.

I’m cognizant that time is fast running out. We’ve probably lapsed the 45-minute.

I’m enjoying this conversation.

The pleasure is mine. We’ve talked about lifecycle marketing email but we haven’t spoken to SMS. Where does it fit now in the ecosystem? For brands that have missed the SMS list-building phase, how do they augment or add SMS information or cell phone number information of their customers? Why is SMS so critical?

Every brand should try to do SMS. If I had to choose between the two channels, I would still go with email first because it runs a lot deeper. If people look into the data around the SMS industries and email industries, SMS is a little bit inflated in terms of how effective it is if you look at like basic attribution windows and things like that. That’s something to consider. Over the last few years, there’s a lot of hype initially like, “SMS is going to beat out email. It’s generating these insane amounts of revenue.” When you dig into the attribution windows, it doesn’t look quite right. That’s something for each brand to decide on its own.

In terms of SMS, because we approach everything from a customer journey and lifecycle standpoint first, we sit down and say, “When does it make sense to communicate this thing through email? When does it make sense to communicate this thing through SMS?” We sit down first and say, “What needs to be said to the customer and when?” From there, which channel would best support that? Is it an email-type communication or is it an SMS-type communication?

Our strategy still skews slightly more on the email side. There’s a lot of opportunity for something like an abandoned cart, let’s say. We might send an abandoned cart email and if they don’t open it, then we send an SMS as a follow-up. Sometimes we’ll flip it. For some brands that we work with, SMS works well for some reactive purchases. In that case, we might say, “If they don’t open the SMS and buy off it, then we send them an email. We see email and SMS more like a one-two punch. It goes back to the whole, what do we want to say to them first and which channel makes the most sense for that?

In terms of list growth, leverage your email list first. The basic tactic here is to make sure you start AB testing and incorporating SMS into your email capture. If you can capture both email and SMS and it doesn’t affect your conversion rates, that’s great. Do that first. At the very least, if someone opt-in to email, you can follow up when they return to capture their SMS for returning customers. If they don’t even opt-in to email, try hitting them again with an SMS request as well. Figure out how to incorporate SMS into your capture but AB test, for sure.

The second one is we use email to grow with SMS lists. We’ll add in banners and flutters to get people to opt-in to the SMS and also leverage your promotions and product launches for SMS as well. SMS gets early access. We have this new product launch coming up. It’s going to sell out pretty quickly. Get on the list. SMS gets the first notification and the email gets the second notification and then it goes out to the broader list. Treat your SMS and email list as VIPs.

Also, be more helpful with your SMS comms rather than sales-y. Only pull that card when necessary like a real urgent sale. This brings me to other communication or chat platforms. We have WhatsApp. WhatsApp is significantly huge. Messenger used to be big at the time Facebook’s dominance. There’s also DM messaging on platforms such as Instagram and Tiktok. Where do you think all this fits in the arsenal of D2C brands trying to deliver a long-term relationship with their customer base?

Our way to think about it is a little bit different in the sense that every channel can be effective for anyone but not for everyone. It’s about finding the right channels for you. If WhatsApp works beautifully for you, it might be the worst investment for another company. It’s more about thinking like, “Are my customers on WhatsApp in the first place?”

I don’t know the demographic of WhatsApp these days. Let’s say WhatsApp is like 35-year-old women or at least 35-year-olds and you’re targeting 19-year-olds who don’t use WhatsApp. This channel is not going to work for you. Do some basic, “Are my customers even using this platform?” The second is, “Do I have the resources to test this thing?”

I find the biggest issue that brands and entrepreneurs run into is like the shiny object syndrome. It’s like, “SMS is working for someone. They made so much money off of it. Someone’s making money off of messenger. Someone’s making money off TikTok.” I’m not on TikTok. I don’t even know if they have chat. It’s that distraction. It’s less so of, would the channel work? It’s more like, do we have the resources right now to spend time on it and do it properly?

A lot of channels can work if you do it properly but most people don’t have the resources to do it all properly. You need to pick and choose. Our approach to developing new services is it’s not our priority to be first to market. If everyone is super high right now about WhatsApp chat, we’re like, “Let’s see if it still stands in a year or two years.” We’d rather be the best in the market than the first to market.

We don’t try to jump on each individual platform. We take some time to wait and see if it works well. Everyone has a different approach. That’s not a right or wrong type of thing. It is more about the conversation of, “Can you get the ROI there? Do you have the resources to do it properly in order to get that potential ROI from that channel or platform?”

The final question is 2020 eCommerce marketing versus 2022. They’re completely two different experiences. Do you want to share bits of light on what you’re experiencing In 2022? There’s an all-time. There’s the recession. Consumers’ discretionary income has significantly dropped. How are best-in-class eCommerce businesses tackling these challenges? What advice do you give to readers? It’s a genuine question I’ve been asking every guest that comes on the podcast.

This is what we’re doing with our clients as well. Best-in-class brands are doubling down on the customer relationship and not using this as a chance for cash-grab. Right now, finances are sensitive for a lot of people going into the recession. At the same time, ads are becoming more expensive. I don’t know what is going on with Facebook these days. It’s been one roller coaster after another.

Acquisition and top-of-funnel are becoming more difficult and more expensive. Now’s the time to focus a little bit more on that retention lifecycle marketing side regardless of whether or not that was the space that we’re working in. There are so many statistics around. It’s five times cheaper to keep a customer than to find a new one.

Right now, focus on keeping your customers and building that loyalty. Going into a recession, everyone has fewer discretionary dollars. Everyone is going to spend a little bit less on luxury items or the not necessary items. It becomes a battle for the wallet around which brands are they going to continue spending with. With that, comes that loyalty building as well.

There’s a little bit more discounting that’s happening. I don’t think it’s a bad thing, especially if you have the margins for it. I do think the best brands are doing it in a careful way and not making it like a flash sale and not making it too gross. How do you position your sales in a way that’s rewarding loyalty and still preserving the quality of your brand but also supporting your customers a little bit more and giving them a little bit more of that breathing room and making things a little bit cheaper?

It’s balancing those two. Build your brand loyalty and double down on making sure you’re creating a great client and customer experience. The worst thing someone wants to feel is like, “I only had $100 to spend this much on something luxurious I was excited for. I bought it and it was a shitty experience all the way through. They kept spamming their things.” That’s not a great retention strategy. Be aware of that. Discount if possible but again in a light branded way.

Jess, I could go on and on. I appreciate your time in sharing Longplay Brands’ journey. For those people who want to find out more about Longplay Brands, it’s LongplayBrands.com. Is your company or are you active on any social media platforms?

We’re active on LinkedIn. In line with the fact that our greatest asset is that we have not done much marketing, we are not super active on a lot of social media platforms. Hopefully, that’s going to change in the future. Our website is still the best place to reach us.

Jess, thank you so much for coming on to the 2X eCommerce podcast.

Thank you so much for having me.


About the host:

Kunle Campbell

An ecommerce advisor to ambitious, agile online retailers and funded ecommerce startups seeking exponentially sales growth through scalable customer acquisition, retention, conversion optimisation, product/market fit optimisation and customer referrals.

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