What High Price Point Brands Get Right About Growth (Most Brands Don’t)

Liam:

Chelsea, excited for today’s episode. Why don’t you give everyone a quick 60 to 90 seconds on who you are?

Chelsea:

Yeah, thanks so much for having me. I’m so stoked to be here. My name’s Chelsea. I’ve worked in marketing for the past 13 years, but my background was actually in actuarial science, risk management, and insurance. I was setting rates for health insurance straight out of college. And I tell people all the time — I hated it. Working in health insurance is so stressful, and honestly it’s devastating to be in that industry day in and day out. So I did what any normal sane person would do, and packed up my bags and moved to New York City. I got picked up by a marketing agency there and they were so fun and supportive — taking my data insights and having me work with incredible companies like St. Jude and Hearst, giving them insights on how their direct mail performance was going. That was the light bulb moment. I went from waking up devastated setting rates for insurance, to giving insights about what was actually making a difference at these huge companies — how could they get more donations, how could they reach the right audience. That was really where I got my start. From there I moved through a few companies — LegalZoom, Ask.com back in the wild west of search days, the dating app world at Match.com when they were big with Tinder, and then back to LegalZoom working with smaller businesses. I fell in love with leading startup marketing teams and have been in that space since. And right now I’m starting one of my own, which is a really fun time.

Liam:

I’ve noticed a trend where marketers don’t always start as marketers — they start in data, like you did. Why do you think that makes someone a good marketer?

Chelsea:

For a long time you just had creatives leading marketing. But once you got into Google and Facebook advertising, where you’re putting real dollars behind immediate interactions, that’s where data and analytical people really stepped up — because they understood all of it and could drive the direction of what was working. I always thought data was where I was going to live forever. I love a good spreadsheet. But I’m also a very creative person. I think marketing draws in people with those varied skill sets and pushes the analytical and creative sides together into one job.

Liam:

What are some key highlights of your career that taught you what great marketing looks like today?

Chelsea:

I was at LegalZoom for quite some time, and I loved that company. The company grew and actually IPO’d by the time I left — we went from working directly with the CEO to having a thousand-employee company. And since LegalZoom does LLCs and business formation, I was around business people 24/7. They were always talking about what businesses were really taking off, what we could support, what they were doing differently. Just being around all of those creative people and understanding what was kicking off their careers was so much fun. Diving into the personalities of the brand and understanding what people were drawn to — it was a lot of unique personalities, which has been really fun to see.

Liam:

What does it take to truly stand out as a brand? The beauty vertical you worked in at Lancer is about as competitive as it gets.

Chelsea:

There’s a lot of trust that needs to be built, especially in saturated markets. For beauty specifically, Lancer Skincare was supported by Dr. Lancer — a Beverly Hills dermatologist — so there’s an inherent trust in the brand because people come to him knowing he’s going to back only what he believes in. Having that front-facing person, someone who really speaks up for the brand and becomes the face of it — we’re seeing that more and more now. It’s almost like the second wave of influencers, because brands are building their own influencer personalities from within.

Liam:

Do you think there’s been a big shift in the influencer marketing world?

Chelsea:

I do. Most of the companies I’ve worked with are pulling back on influencer spending. A big reason is that general UGC content is doing so well — a normal person talking about their experience with a product performs just as well as a paid influencer when you put it into a Meta ad. And there’s been so much backlash around beauty influencers especially, because people know they’re getting sent dozens of products and just talking through each one. It’s not what they actually reach for at the end of the day, so it doesn’t feel genuine.

Liam:

Can you get the same reach by creating something in-house and putting it on TikTok or Reels, or does it take more iteration?

Chelsea:

It takes more iteration — it’s definitely more work. If you want that quick flash in the pan, paying an influencer for reach makes sense. But you’re not building trust with it. People can see through it. So it really depends on whether you want to grow quick or have long-term staying power. I’m firmly in the long-term camp.

Liam:

What does thinking long-term look like in reality? Because in most team meetings it’s all about hitting this month’s or this quarter’s numbers.

Chelsea:

I’m seeing a lot of people in the freelance and agency space doing a better job of over-communicating how long it actually takes to build awareness and trust — making sure people remember you when they’re actually in market for the product. And that conversation is gaining more value in boardrooms. I’m having fewer conversations about “why aren’t we hitting our numbers right now” because founders and C-suite leaders seem to be increasingly understanding that there are long-term processes you have to go through.

Liam:

What are some of the biggest mistakes brands are making right now when it comes to awareness?

Chelsea:

I see so many people throwing money at Meta ads without knowing what it’s actually doing for their brand. They’ll say, “our ROI is horrible but it’s building awareness, people are seeing us, we’re spending a lot.” And I’ve definitely talked to people who are almost cocky about how much they spend on Meta. That’s not necessarily building the awareness you want. Are you tracking these people? Are they coming back? Did they sign up for your email list? Most of the time they just don’t know. So I ask — why are you spending so much? Understanding the full flow of what your customers are doing and what each dollar is actually getting you is so important.

Liam:

It seems like a lot of brands are coming back to the basics of retention. We’re seeing brands aim for at least 20 to 30 percent of monthly revenue from retention tactics. How are you thinking about it?

Chelsea:

I’m looking at those same numbers — at least 20% of revenue through email flows. There’s been so much conversation around browse abandonment and add to cart emails, and it’s so interesting to go from a few years ago when those were just a given — kind of ugly, just turned on — to now seeing some of the most elaborate abandoned cart flows I’ve ever seen. Five emails long, really thoughtful about how they’re introducing the brand, speaking to the specific item abandoned. That would have been unheard of two years ago. A big reason for the shift is people got burned out on Meta, so email feels like — well, we’re already paying for the platform, let’s make it really work. And marketers are recognizing their own personal behavior too. My friends tell me they sign up for a brand and then wait three days for that abandoned cart email to trigger just to get the 20% discount. So marketers are thinking — okay, this is what people are doing, how do I reconfigure my whole plan around that?

Liam:

Lancer has a pretty high price point. What are the retention strategies you use with a product like that?

Chelsea:

Almost all of the jobs I’ve had in the past few years have been high AOV products. When you have a high-value product there’s a little more wiggle room with ads, but I’m thinking about lifetime value on a much longer playing field. I worked for a bed linens company where sheets were around $300 a set. With products like that I’m thinking I’ll probably be talking to that customer for two to three weeks, maybe two to three months, before they purchase. So I build out all these strategies knowing I don’t want to annoy them, but I want to inform them and give them little nudges throughout the journey. And then I have to think about repeat purchases — if someone just bought $200 worth of skincare, I’m not telling them to come back and buy more skincare in three weeks. I have to map out the timeline of when to re-engage them later in the lifecycle. It’s a harder conversation to have with the C-suite too, because they want revenue now.

Liam:

Something you’re super passionate about outside of email is conversational SMS. What are your thoughts there?

Chelsea:

I love SMS as a channel — that comes from my own personal behavior as a consumer. When I’m making a larger purchase, I want to really make sure I’m buying the right thing, and most people want to talk to another person and get that validation. SMS and customer service tie so closely together. The conversations on our SMS should feel like they’re genuinely coming from us. There are great AI platforms that can engage with customers, but I also encourage our customer service team to be in there too, responding to SMS and email, having those real conversations. We’ve had our CS team pop in and say “hey, we actually don’t recommend that product for you — here’s what we’d suggest instead.” Having that direct relationship is really helpful. With high AOV products especially, I’ve had customers find my personal email or phone number to track down an answer. People are craving that validation — yes, I’m making the right purchase, this is good for my money. I tell our team to be honest. If it’s not something they’d recommend, don’t recommend it. We’ve integrated AI into our SMS but baked in rules — don’t just push the bestseller because it’s popular, make it customized per person. SMS is just so much more personal. A recommendation showing up on your phone sits differently than an email or a quiz.

Liam:

What about SMS in flows and retention marketing?

Chelsea:

I have a love-hate relationship with it because you’re paying per message, so you have to justify every flow. But I do think it’s more personal — I respond way better to an abandoned cart text than an abandoned cart email. So I keep that in mind when building SMS flows. I’m a lot more strict about triggers for SMS than email. I want some other signal that they’re actually engaged — they did X, Y, Z — rather than just “they were on our website, send them a generic text.” And I update SMS flows way more than email flows — every other month I try to refresh the copy. Because if you’re buying skincare every two to three months and you’re getting the same text every time, you can scroll back and see it. That’s not personal and it doesn’t feel good for anyone.

Liam:

Do you think AI will change personalization in email and SMS?

Chelsea:

Yes, and I was just talking to a friend who’s a copywriter and it’s honestly a little scary for people in that role. There are so many tools now personalizing messaging — you may just have a base statement and then it fluctuates based on dozens of different attributes. I always try to keep in mind when integrating new tech: is this actually what the customer wants? Is that personalized tone or mention actually beneficial? If I don’t see it as a real customer need, I don’t integrate AI unless I have to.

Liam:

Do shoppers expect a more personalized experience now?

Chelsea:

Yes, absolutely. To me it reflects something deeper — people are more lonely, craving more one-on-one conversations, and I think they’re looking for that from brands too. They want it to feel like a friend telling them what to buy. For a long time, especially as a millennial, word of mouth was everything — if a friend recommended something I was going to buy it. People really want that feeling now, where it feels like a conversation with your buddy. That’s why people default to chatting with customer service — they want that connection on the other end of the line.

Liam:

Where do you think AI in marketing is a hell yes versus a hell no?

Chelsea:

I have a really hard time with anything that replaces creativity. I’m also a photographer — concert photography is my nighttime. AI influencers, AI UGC, AI photo shoots — that one’s hard for me. It’s very hard to come to terms with replacing creativity with a computer. Ideas-wise it’s more of a gray area — bouncing ideas with AI can be helpful, though it does take away from personal relationships and understanding what people actually want. But things like finding a new audience for you, integrating into the system to create better triggered emails at the right time — very happy to integrate AI there.

Liam:

Let’s spend a few minutes on your new business. What are you working on?

Chelsea:

I’m starting my own camera bag company called Cryptid Camera Bags. I’m a concert photographer — that’s my nighttime job. A few months ago I was talking to my husband and I had this whole rant about how I couldn’t find a camera bag that fit my style and vibe. I can’t show up to photograph Iron Maiden with a pink little tactical backpack. That’s basically the whole market. I did a lot of research and couldn’t find anything in that space, and my husband said — why don’t you do it yourself? So I’m finally diving in full-time. It’s a wild career pivot to go from helping other people market and build their businesses to doing it completely on my own. But having all that experience and all these people I can lean on — I’ve got my fingers crossed.

Liam:

What are the learnings you’re taking into the new business? What mistakes have you seen founders make that you’re being conscious of?

Chelsea:

I think a lot of founders get very personal about what they want — and of course this is personal for me, I’m building the camera bag I couldn’t find. But I’m also coming in with the awareness that I need to make sure it works for other people, not just me. So I’m going into it with a lot of customer interactions, a pool of people who will give me feedback before we go to mass production. The vision is still mine, but I need to fit a need that’s wider than me. I don’t want to end up with something uniquely made for myself that doesn’t work for others. I’ve worked with a lot of founders who hold on to things too tight — “this is my baby” — and won’t expand or grow based on feedback. It hurts the business. So I’m being very intentional about taking the feedback and running with it.

Liam:

What do you think marketers must be experimenting with over the next 12 to 24 months to stay ahead?

Chelsea:

I think it’s twofold. First, your team — you need them to be strong ambassadors for the company. Second, your existing customers. If your current customers aren’t also ambassadors — telling other people they need to buy your product — you’re losing out. So you have two bases of really solid people who can go out and talk about your products: your team and your retention audience. If you make both of them very strong supporters of your brand, that foundation carries through months if not years. Then take that knowledge and drive it toward acquisition — figure out why they came to you in the first place and feed that forward. Those two sets of people are really where you need to lean in.

Liam:

Thanks so much for coming on. It’s such an interesting time — brands dying faster than ever, but others growing exceptionally quickly. Exciting times to start something new. Congrats on the business.

Chelsea:

Thank you so much for having me. It was lovely to sit down.

We get into why high-ticket products require longer buying journeys, how to build trust across weeks or even months, and why retention, SMS, and real customer conversations matter more than ever.

We also cover:

Why brands are overspending on Meta

The shift away from influencer marketing

How to think about retention vs acquisition

Where AI is a “hell yes” vs a hard no

No matter what price point you’re selling at, Chelsea shares practical takeaways every marketer can use.

0:00 Intro 2:30 Why Data-Driven Marketers Win 6:10 What It Takes to Stand Out as a Brand Today

8:30 Why Influencer Marketing Is Losing Trust

11:55 The Biggest Mistake Brands Make with Meta Ads

13:15 Why Retention Matters More Than Ever 16:10 How High Price Point Products Change Your Strategy 18:50 The Reality of Longer Buying Journeys

19:20 Why Conversational SMS Works

24:20 AI in Marketing: Where It Works (and Where It Doesn’t) 27:25 The Line on AI and Creativity

29:30 Building a Brand from Scratch 31:20 Lessons for Founders (What Not to Get Wrong)

33:20 What Marketers Should Focus on in 202635:20 Final Takeaways