Lance Dobson runs marketing for a healthcare-compliant telehealth brand, where privacy regulation strips away identity-based targeting entirely. His counterintuitive take: that constraint made the marketing better, not worse, forcing a return to understanding the customer's actual problem instead of leaning on an algorithm to paper over not knowing them.
Behind the Expert
Lance Dobson has spent 15 years in e-commerce, the last decade largely inside healthcare and healthcare-adjacent brands. He started as what he calls an "agency kid," then moved through outdoor retail — including a stretch at Backcountry — before landing at Adobe, where he consulted on the Adobe Ad Cloud's algorithmic search-bidding tools for accounts like 1-800 Contacts and later joined 1-800 Contacts in-house. From there he worked with a CPAP brand and other healthcare-adjacent companies before arriving at Shed, a telehealth brand built around GLP-1 weight loss and whole-person wellness, where he now leads marketing data and analytics. Having worked the agency, ad-tech, and brand sides of the business, he argues that healthcare's strict privacy rules — usually treated as a pure constraint — forced his team into a marketing discipline most unregulated brands skip entirely.
The Quick Hits
- Healthcare privacy law strips out most identity-based targeting and retargeting. Shed has to anonymize data end to end, which removes a lot of the tracking infrastructure other brands lean on by default — in Dobson's words, "it's not like it can't be done, it's just — it's a lot."
- That constraint became an advantage, not a handicap. Without hyper-personalization as a crutch, the team was pushed back to a simpler discipline: understand the customer's actual problem and show it, rather than infer who they are from a data trail.
- People don't care how much you know until they know how much you care. The "oh my gosh, that's totally me" feeling — the same one that makes stand-up comedy or a Progressive Insurance ad land — comes from naming a shared problem or moment, not from a demographic segment.
- Persona-based marketing can become a "too high resolution proxy" for the real thing. Diced finely enough, it starts to resemble marketing's version of analysis paralysis. Dobson's fix: start from the customer's problem and solution, then layer personas outward from there — not the reverse.
- Retention outweighs acquisition in headcount by roughly four to one or more at most companies, once you count ops, customer service, and lifecycle teams propping up a lean paid-acquisition function — a dynamic he sees as even more pronounced in a healthcare product people depend on continuously.
- Don't lead with "we're privacy-first" as a marketing claim. Saying it out loud can plant a doubt that wasn't there before — customers start wondering whether you weren't before, or whether everyone else isn't. Better to make trust implicit in the product experience itself.
- AI's proven use case on his team so far is analytical and light coding work — he estimates it's replaced the output of one to three developers — plus ideation and content structuring. Final content stays human-written, and new AI tooling has to clear Shopify's bar: prove AI can't do the job before you hire for it.
Fifteen years in e-commerce, most of it in healthcare
Dobson's career runs through three different vantage points on the same industry: agency, ad-tech, and brand. He started, as he puts it, as an "agency kid" — a path he thinks produces the deepest generalists, because low agency pay is offset by exposure to more accounts, more industries, and more disciplines than a single brand role can offer. From there he moved through outdoor retail, including a stint at Backcountry, before landing at Adobe, where he worked on the Adobe Ad Cloud's algorithmic search-bidding products for large accounts, including 1-800 Contacts — then joined 1-800 Contacts in-house for several years. A CPAP brand and other healthcare-adjacent work followed before he arrived at Shed.
What Shed is building
Shed began as a weight-loss-injections brand and is expanding toward what Dobson describes as the most complete fitness and wellness solution — not there yet, but building toward it. The most recent addition is a weight-loss lozenge, a troche-style medication aimed at customers who are injection-averse, alongside longevity and vitality solutions and hair-loss treatments. The part he considers a cornerstone rather than an add-on is the coaching layer — human-aided programs that sit alongside the medication itself.
People don't care how much you know until they know how much you care
Dobson's central argument for marketing in a "generic" category — his word for weight loss, GLP-1, and longevity right now — is that customers aren't looking to be understood as a demographic. They're looking to feel understood as a person with a specific problem. He points to comedy as the clearest version of the mechanism: audiences respond to a joke, dark or clean, the moment it produces an "oh my gosh, that's totally me" reaction.
He extends the logic to category advertising that has nothing to do with healthcare — Geico, Pepsi, Progressive's "don't become your parents" ads — arguing they work because they capture a shared day-to-day moment rather than pitch a generic product. He also points to the proliferation of intake quizzes across self-help and wellness brands (BetterHelp, Talkspace, Strawberry.me) as the same instinct in a different form: even a manufactured, templated quiz can make a customer feel like the company is about to assign them something built for their specific needs.
The trap of persona-based hyper-personalization
Asked whether Shed's privacy constraints push the team toward persona-based marketing as a substitute for identity-based targeting, Dobson pushed back on personas as a full answer. He worries hyper-personalization becomes a "too high resolution proxy" for the thing that actually matters — diced finely enough, it starts to resemble analysis paralysis rather than insight.
His preferred sequence: start from the customer's problem and the solution, build the ad-to-landing-page-to-conversion experience around that, and layer persona-level refinement outward from there — not the other way around.
Privacy as an unspoken promise, not a marketing claim
Given his public stance as privacy-first, Dobson was asked whether that shows up explicitly in Shed's marketing. His answer: deliberately, no. He compares announcing "we're privacy-first" to the moment of pulling a splinter out of a kid's hand — better handled without drawing attention to it.
In his read, trust is better built implicitly — through an intuitive site experience and a product that clearly takes care of the customer — than asserted directly in copy, where the claim itself can introduce doubt that wasn't there before.
Retention outweighs acquisition by four to one
Asked how he splits time between acquiring new customers for a net-new brand and retaining existing ones, Dobson reframed the question around headcount rather than budget. Counting only the marketing team, the ratio might look close to even — but widen the lens to ops, customer service, and lifecycle, and retention dominates.
AI: useful for coding and ideation, not yet the final decider
Dobson's take on AI is deliberately unhyped for a highly regulated, trust-dependent category. The clearest win so far has been analytical and light coding work — he estimates it's replaced the output of one to three developers on his team. Content is a different story: he uses AI for ideation and structuring, but keeps human writers as the final decider on anything that ships, given how directly the content touches the trust relationship with customers.
For deciding when a new AI tool or workflow earns its place, he borrows a framework from Shopify's internal AI mandate: before you hire for something new, you have to make the case that AI genuinely can't do the job first.
Sound Bites
- “You've got the agency space, the tech space — the ad tech, mar-tech space — and then you've got the brand space. You get to see a little bit behind the curtain on the algorithm, what the incentives are for these tech companies trying to sell to you, and how to partner with them.”
- “I don't want to be the company that's just flinging vials at people and saying "inject yourself with this." We want to be a customer- and patient-first platform, with humans who help walk you through using these so it's sustainable — actual person-first solutions.”
- “People, customers, patients, clients — people don't really care to understand you. They care if you understand them.”
- “Persona-based can become a too high resolution proxy for addressing the problems that people are encountering, versus helping them feel understood at the level of the problem and the solution. It can look and feel like marketing's version of analysis paralysis — you're dicing it apart, dicing that apart, and you end up with a tree of hyper-personal segments that may not actually help people feel understood, may not build a relationship, may not target people where you need to.”
- “I want the expectation to just be that we're privacy-first, full stop. If we start saying that we are, I worry people will start questioning whether we actually are — because if you say you're privacy-first, people think, well, I assumed you already were, so why are you telling me? I've seen that happen — people weren't thinking about it, and now they're thinking about it, and now they're worried about it.”
- “I'd be willing to wager that at almost any company you step into, the number of people devoted to retention is at least four-to-one over acquisition — probably more. You'll have one to three max paid-search and paid-media people, a couple of people who do SEO, maybe a couple of writers. Then you have an ops team, plus the email marketing team, plus the customer service team, plus, plus, plus. So I still think retention is king in this particular domain.”
- “AI is tricky to me because in spite of all the tools and all the ways people talk about it, it's still mostly a one-to-three-trick pony as far as I'm concerned. It can help with coding like crazy, and that's a pretty big trick. But I just don't want it to be the thing that ships — I still employ writers, and I still want my content to be human-written.”
The Chord take
Dobson's argument inverts the usual complaint about healthcare marketing constraints. The instinct is to treat compliance-driven data limits as a tax on performance — less targeting, less personalization, less signal, therefore worse marketing. His experience running growth for a telehealth brand says the opposite happened: stripped of identity-based targeting and retargeting, his team had no choice but to get better at the thing personalization was always supposed to be a proxy for — understanding the customer's actual problem, well enough to say so plainly. That's also his warning about persona-based marketing for teams that do have the data to hyper-target. A persona, sliced finely enough, starts to feel like precision, but it's still a proxy — one more layer removed from the problem itself, and easy to keep slicing past the point of usefulness. The same discipline shows up in how he treats privacy as a brand claim: stating "we're privacy-first" out loud can create the doubt it's meant to resolve, because it invites the question of what wasn't true before. In each case, the stronger move is structural rather than declarative — build the experience so trust and understanding are evident, instead of building the copy that says they exist.
Put it to work
- 1Before adding another layer of persona-based targeting, ask whether it's getting you closer to the customer's actual problem or just slicing an existing segment finer. If you can't say what problem a persona uniquely captures, it's probably not earning its complexity.
- 2Audit your acquisition-to-retention headcount ratio, counting ops, customer service, and lifecycle teams, not just paid media. If retention isn't outweighing acquisition by something close to four to one, ask why not.
- 3Before writing "privacy-first" or a similar trust claim directly into marketing copy, consider whether it introduces a question customers weren't asking. Where possible, make the promise implicit in the product experience instead of explicit in the copy.
- 4Bring in an outside perspective — an audit, a new consultant, a different agency — on a fixed cadence, not just when something is broken. Regularity is what keeps a team from tunnel-visioning on the vendor or approach it already trusts.
- 5Before greenlighting new AI tooling, apply the test Dobson borrows from Shopify: make the case that AI can't do the job before you build or buy for it. Treat that as the default bar, not an exception.
- 6If you're in a "generic" category, invest specifically in messaging that names the customer's day-to-day moment or problem, the way Progressive's parent-behavior ads or a well-built intake quiz does — rather than differentiating on product claims alone.
Full transcriptShow ↓
Bryan Mahoney
How's the weather there in Utah, by the way? Did you guys finally get snow?
Lance Dobson
It's really disappointing, actually. This week it's supposed to get up into the 50s, and it's the middle of December. I don't know what's going on — everyone said the Farmer's Almanac had Snowmageddon coming, but I haven't seen it yet. So if it's coming, it's going to be all in one shot here in January and February.
Bryan Mahoney
Yeah, I don't know what's going on either. I'm a skier, and I've been doing my snow dance — I'm up at Mammoth Mountain most of the time, and we got some snow in October, a little in November, and it's kind of the only thing that's open. I've just been watching the snow reports in Northern California and Utah, wondering when it's going to happen. Not too much here, so hopefully it starts dumping over there soon. But we're not here to talk about snow — well, not mountain sports, at least not yet.
Lance Dobson
Me too. Need it.
Bryan Mahoney
So I'll kick us off. Thanks for tuning into another episode of the Brilliant Commerce Podcast, where I'm lucky enough to get a chance to sit down with some of the brightest minds behind some of today's iconic — or, as I like to say, soon-to-be-iconic — brands. Today I'm joined by Lance Dobson, coming to us from Salt Lake City, Utah. Lance is Head of Marketing Data and Analytics at Shed, the telehealth brand helping people navigate the GLP-1 and whole-person wellness industry. Lance has a fascinating background and career that spans stops at a number of really amazing brands that I'm excited to learn from and unpack. So with that, Lance, welcome to the pod.
Lance Dobson
Thanks for having me, Brian. I'm stoked. Stoked to chat.
Bryan Mahoney
My first question is where am I finding you? But I already sort of let the cat out of the bag that you're in Salt Lake — but yeah, maybe take a couple of minutes and tell us a little bit more about your background and what led you to Shed.
Lance Dobson
Yeah, for sure, man. I'm historically an e-comm guy — I've worked in e-comm for 15 years, and in the past 10, mostly healthcare, although it's been a bit of a hodgepodge. Started off as an agency kid like everybody does, made my way through a couple of really kick-ass brands, made a stop doing kind of tech — not sales, but account management and strategy — and have been back in the health and e-comm space for a while now.
Bryan Mahoney
Okay. Yeah, one of those brands I saw was Backcountry — I've been a customer of Backcountry for a little while, sort of a real fan. The agency thing is interesting — there's been a number of people on my podcast who either grew up through agency and then went in-house, or did the inverse. I did agency first for nearly 20 years before going in-house and then ultimately finding my way into software. Do you think there's a right way of doing it? If you could rewind the clock, would you do in-house first and then go to agency, or do you really appreciate starting at an agency and getting the opportunity to see all those brands before ultimately landing where you are?
Lance Dobson
This is a fascinating question, because I think it depends on your learning style a little bit. The thing I really liked about agency life — and it depends on the agency, of course — is that at the low level, you typically don't get paid great. So what you get paid in is opportunity to learn, I think. That was my experience, and what I saw when I look at — I keep calling them 'agency kids' because it seems like a lot—
Bryan Mahoney
Yeah.
Lance Dobson
—of people grow up in marketing at an agency. I think the vast preponderance of marketers probably do, just because of the numbers — a lot more people can be at an agency than can be at a brand. So you get to see a lot of accounts, a lot of different industries, a lot of different areas you can learn from — brand marketing, SEO, performance marketing, copy, you get to learn a whole bunch of things at an agency. It seems like you can do that at a brand too, but it's just not as accessible across multiple areas. But if you happen to find a thing that really resonates with you, you're able to go five miles deep at a brand. So I think there's a little bit of luck, a little bit of learning style involved — I'd say typically the agency-first route is going to be better, but I know, like you said, a number of people who strike it rich going the other way around.
Bryan Mahoney
Yeah, I think the opportunity to go deep — I don't think one is necessarily better than the other. I know I really appreciated being able to get to know multiple brands, try things out, and share those learnings across accounts — I thought that was interesting too. That was one of the reasons some of the brands that chose to work with my agency at the time recognized the work we did and wanted to learn from it, not necessarily copy it. I do think that if you're starting out in your career, the opportunity to see a lot is really useful, but then eventually there's the opportunity to say, I really want to sink my teeth into this brand, get to know our customers, and spend more time here. I consider myself fortunate to have done both, and it sounds like you'd say the same thing.
Lance Dobson
I'd say maybe there's a third possible track as well, and I'm fortunate that I got to land in that too — my time at Adobe. You've got the agency space, the tech space — the ad tech, mar-tech space — and then you've got the brand space. I was fortunate to step into all three of those tracks, and again, like you said, they each have their benefits. But where the ad tech, mar-tech space has its benefit is that you get to learn—
Bryan Mahoney
Yeah.
Lance Dobson
—the backend of the tech that both the agency and the brand are using. You get to see a little bit behind the curtain on the algorithm, a little bit of what the incentives are for these tech companies trying to sell to you, and understand that — how to partner with them, how to communicate with them, how to communicate back to the brand. So I think there's also that track as well.
Bryan Mahoney
Yeah, talk to me a little bit more about the role at Adobe. Obviously a massive company that does an awful lot — what was your role there? What products did you get to work on?
Lance Dobson
Yeah, it was really fun during the time I was there, because I got to touch a number of very, very cool brands. I was on the Ad Cloud, mostly Ad Cloud for search — historically I'm mostly a search guy, paid and organic — but I got experience in a variety.
Bryan Mahoney
Mmm.
Lance Dobson
With the Ad Cloud, the idea at the time — because the algorithms were still pretty new as far as algorithmic bidding — was essentially taking tech and layering it onto the search platforms to do the bidding, supposedly better than the ad platforms could do themselves. That's changed drastically since — Google and even Bing have much better algorithms now, much more closely tied to their own data. They've kind of built their own walled gardens, so it's different now. But at the time, that was the game, and Adobe did a pretty good job — it was like the Kenshoos, the Marins, the Adobes of the world. That was the game. So essentially, we'd go into companies and say, you have a medium-to-large search business, we want to come in, make it more efficient, enhance your reporting, layer in a bit of agency-style consulting, and help grow your business.
Bryan Mahoney
Okay, you said 'game,' and I remember the early innings of SEO when it did feel like a bit of a game. We'd see the algorithm change, we'd try to reverse-engineer it, all sorts of strategies — creating backlinks, shadow content, whatever it took to get on the first page. It sounds like some of the work you did at Adobe was adding structure to that game — how do we make it not a game, but leverage data to give insights so you can make the content actually better, more authentically deliver results? As we see the landscape changing again under our feet, with agents doing more of this discovery for us — what advice would you have for people who grew up in SEO with a strategy that's worked well, to adapt it so it's not a game with these agents, but so they stay ahead? Or is it still too soon to say?
Lance Dobson
Right now it seems like, in some ways, the more things change, the more they stay the same in this particular area. It's just — keep your ear to the ground, aggressively research, stay well connected. We've been holding on for dear life on the SEO side here at Shed, honestly — but I'd say bring in multiple perspectives. It can be easy — and this is a luxury I have, because I have the experience to know which—
Bryan Mahoney
Yeah.
Lance Dobson
—perspectives to bring in. But it's really easy to say, 'I like this tool, I like this provider, I like this consultant, I'm going to stick with them.' I think it's important to remain skeptical and bring in new perspectives with regularity — that's the case in most marketing, because it's easy to get narrow-minded, tunnel-visioned on what you're working on. Find a thing that works, bring in another perspective, do an audit — make sure it's incentivized right, make sure it's not an agency that wants to win your business, that it's an audit for the sake of the audit — bring in another consultant to look at things, give advice, dice it apart, and do that with some regularity so you're not stuck in that feedback loop, I think.
Bryan Mahoney
Yeah, I found the same thing — I like what you said, the more things change, the more they stay the same. The shift to AEO from SEO hasn't really felt like much of a shift, especially considering SEO became less of a game once it became something you could actually understand. Good content matters — the agents, the robots, are seeing the same thing we as humans are seeing, and there's no way to cheat it. You've got to keep making good investments and measuring them well. I think the advice of bringing in outside perspective — maybe this brings us back to the agency conversation — it's one thing to see the traffic your brand is getting, but how do you understand how that compares to what others are seeing? We're all in it together — whether you're working with agencies, or going to conferences and asking colleagues what they're seeing and what's working — keeping your ear to the ground and staying willing to learn and adjust is probably the best advice we can give. I'm curious — you mentioned you're at Shed, a relatively new brand, if I understand correctly — can you tell us a little about what you're selling and why the brand was created?
Lance Dobson
Yeah, I agree.
Bryan Mahoney
— because I want to get into the importance of brand, but first let's level-set on what Shed is.
Lance Dobson
Yeah. Shed began as a weight-loss-injections brand. Right now, the vision is for it to become the most complete fitness and wellness solution — that sounds like big things, and we're not there yet, but we're building toward it. A lot of what we do today is a smaller subset of what you'll eventually see on the site. We do weight-loss injections, and we just released a very exciting new weight-loss lozenge — a troche-style medication — this week, which is really timely. It's for people who are injection-averse, and there are plenty of those. We're gathering data on—
Bryan Mahoney
Whoa.
Lance Dobson
—the efficacy, but the initial results are super exciting. So, really exciting things in the weight-loss space, especially for people who want options that aren't injection-related. We also have longevity and vitality solutions — energy-boosting and things like that — as well as hair-loss treatments. That's what we are right now. The thing I'd add — it's the icing on the cake, but also in some ways a cornerstone — is our coaching, our human-aided programs. I don't want to be the company that's just flinging vials at people and saying 'inject yourself with this.' We want to be a customer- and patient-first platform, with humans who help walk you through using these so it's sustainable — actual person-first solutions. That's what Shed is in a nutshell right now.
Bryan Mahoney
I love that. I imagine so much of the success runs through the relationship you're able to establish with your customers.
Lance Dobson
Yeah, 100%.
Bryan Mahoney
Relationships — I kicked us off saying I love using the term 'iconic brands,' or 'next-to-be-iconic brands.' I think you can't be iconic without a healthy cohort of customers who really believe in you and support the brand. And I say this with all respect — when I think about weight loss, or GLP-1, or even longevity, there's an awful lot of interest in the space right now. It's what I'd call a generic category. If that's fair, how do you, as someone in charge of growth and marketing, looking at the data, advocate for the importance of brand investment in order to really stand out and win in a category that's somewhat generic?
Lance Dobson
Yeah, it's a fair question. In some ways it goes back to the blocking and tackling of marketing in general. I'll invoke a truism here — there's that thing where people don't care how much you know until they know how much you care, which is the grandma's version of saying—
Bryan Mahoney
I like that.
Lance Dobson
—people, customers, patients, clients — people don't really care to understand you. They care if you understand them.
Bryan Mahoney
Whoa.
Lance Dobson
When people see a site that's easy to navigate, part of why they like it is because they think, okay, this site understands how to take care of me. People are self-interested that way, as they should be. So I think the right answer is always: how do we show that we understand you? A lot of the best content—
Bryan Mahoney
Yeah.
Lance Dobson
—I see out there these days really emphasizes that. You can even see this in comedian content — I consume a lot of stand-up comedy, and the thing people respond to best, whether it's overtly funny or dark and crazy, is when they go, 'oh my gosh, that's totally me.' It's like that comedian sees me and they've never even met me. Same with marketing in a lot of ways.
Bryan Mahoney
Yeah.
Lance Dobson
It's like, oh my gosh, this ad gets me. I see this a lot in the self-help space, honestly — the BetterHelps, the Talkspaces of the world, Strawberry.me is another good example. Even an app I saw that was designed to teach AI had a bunch of courses — this is why I think there's been a huge proliferation of quizzes, quiz-style forms to get people in. Even though it's about the company understanding the customer, I think people feel like by filling that out, the company—
Bryan Mahoney
Yeah, that is right.
Lance Dobson
—is understanding them and assigning them a treatment, a product, an intervention that's married to their specific needs. That's why I think the focus for marketers, especially in a generic category, is to find ways to say, 'I see exactly where you are.' It almost doesn't matter — that's why the Geicos, the Pepsis of the world create marketing that's just about day-to-day experience. I'm thinking of Progressive Insurance, and what happens when you become a parent, or—
Bryan Mahoney
Yeah, yeah — 'don't become your parents.' Those ads crack me up. That's a generic product — they're selling me insurance, but who do I want to be associated with? Do they get me? Can I see myself becoming my dad? Yeah.
Lance Dobson
Yeah, they understand me. You cringe and go, 'no, I am becoming my parents.' And so you feel understood — you relate to it. I think that's maybe the most important thing, and honestly it's just good life advice in interacting with people generally: if you want to be a value-add in the world around you, you have to learn how to help people feel understood by you.
Bryan Mahoney
Yeah, so again it comes back to — the more things change, the more they stay the same. You're describing traditional marketing, and when there's data capture, that's where you're establishing that trust relationship with a customer. There's a responsibility as a brand to demonstrate you're going to do something with it — there's a fair value exchange. I'm telling you something about myself, maybe something personal, and the healthcare side of this makes that even more important. It's not just about encouraging you to add something to cart — I want to establish a relationship that brings you back. And you're ultimately selling a product that customers are going to put in or on their body, so the bar for trust is even higher. So it's about understanding customers, I think—
Lance Dobson
Yeah, 100%.
Bryan Mahoney
—which isn't always the easiest thing to do, or to pull off well, and authentically. You've done marketing, acquisition, and retention across a number of brands — including outdoor goods. Are there any challenges specific to healthcare, to data capture, that surprised you? Any advice you'd give to others in this space?
Lance Dobson
Yeah. I've worked in healthcare or healthcare-adjacent for 10 years — whether consulting at Adobe, or in-house, I consulted with 1-800-Contacts for a number of years while at Adobe, then was in-house there for a handful of years. I've also helped a CPAP brand and a couple of others like that — again, generic category, nothing sexy or fun about CPAP. The difficult thing is always compliance and privacy. There's a layer of privacy you have to adhere to that has legal standards — that one's always tricky. I've said before, that one's about making sure you can give your attorney a hug and he'll hug you back, so you can get good oversight on how you manage your data and your agreements. What it means in effect is you don't get to use a lot of the traditional—
Bryan Mahoney
Yeah.
Lance Dobson
—tracking enhancements that come with a lot of platforms, because you have to anonymize everything, which is an extra step, and you have to make sure you have all your ducks in a row — and if something goes wrong, you have to report it. It's just a lot. It's not that it can't be done, it's just — it's a lot.
Bryan Mahoney
You've mentioned before — I've read and listened to some of what you've said — you're kind of on record as a privacy-first person for your customers. How do you think about incorporating privacy as a brand promise? Is that something that comes through in marketing, or is it built into what you do without being said outright?
Lance Dobson
That's a good question. If you go look at the Ad Preview tool on Meta and look at the ads we have out there, we don't do a ton of that. I go back and forth on this one — it's a fascinating question, because on the one hand I think it could be a thing, but on the other hand, you almost don't want to. It's kind of like when you're pulling a splinter out of your kid's hand — you want them to look away while you do it. So it's the kind of thing where—
Bryan Mahoney
Yeah, yeah, huh.
Lance Dobson
—I want the expectation to just be that we're privacy-first, full stop. If we start saying that we are, I worry people will start questioning whether we actually are — because if you say you're privacy-first, people think, well, I assumed you already were, so why are you telling me? I've seen that happen — people weren't thinking about it, and now they're thinking about it, and now they're worried about it.
Bryan Mahoney
Right.
Lance Dobson
So, I don't know.
Bryan Mahoney
Yes, so maybe another way of saying it is — if you do your job as a brand and establish the relationship, the customer is happy to be there. You mentioned UX, the investment there, making sure the site feels intuitive, that you're taking care of the customer and understanding them. Maybe that's a way of making the trust implicit, rather than explicitly saying 'we're privacy-first,' which invites the question — wait, does that mean you weren't before? Is everyone else not?
Lance Dobson
Now I have questions.
Bryan Mahoney
I mean, obviously — well, not obviously, but I see Apple ads everywhere. They've decided Safari is going to take this stance as the privacy-first browser. I've been a privacy-first person for a long time myself, sometimes to the disappointment of my marketing counterparts, when I was expected to deliver the stack they wanted to use to acquire customers. I've always wanted the brands I'm associated with to use customer data the way I'd want my own data used — sometimes that standard is really high. But when I see a company like Apple investing millions of dollars buying billboards to say 'Safari keeps you safe,' I keep coming back to: do customers really care these days? Or do we just feel like our data is an asset we're happy to give away as long as the value we get back from the brand is meaningful? I don't have a right answer, but I continue to be fascinated watching these investments, and talking to people who don't have a choice — given the industry they're in — but to think about this in a privacy-first way. What I'm hearing from you is that you're trying to create those trust relationships with customers in a way that isn't overtly built into the branding.
Lance Dobson
I think so, right now. It's difficult to tell — we test a lot, and it's very possible that at some point we decide this would engender more trust. But right now, this is my intuition, and intuitions in marketing seem to be wrong very often, so there's that.
Bryan Mahoney
Okay.
Lance Dobson
I think people are maybe a little tired of having scare or anti-scare messaging thrown at them constantly. It's like, 'we're going to keep you safe' — and people are thinking, can you just be safe and not have to bring it up? Because I don't want to have to worry about it.
Bryan Mahoney
Yeah. Can that be table stakes?
Lance Dobson
I'm just tired of being worried and scared all the time. So in some ways, that's my intuition on it. But I'm always open to an interesting test — so who knows?
Bryan Mahoney
Well, I think being willing to be wrong is really important. All the best marketers I know trust their gut, and they're also the first ones willing to say, 'I got that one wrong, the customer surprised me,' and pour that learning into the next thing they do. The other thing I wrote down as you were talking is this idea that you can't take advantage of some of the retargeting tools, given that—
Lance Dobson
Yeah. Yeah.
Bryan Mahoney
—you're healthcare or healthcare-adjacent. As I think about the landscape for acquisition and retention today, given we're moving quickly into a more privacy-first world — customers choosing privacy browsers, the ability to be anonymous becoming almost automatic — I'm seeing some marketers shift away from hyper-personalization and more into persona-based marketing, with some really interesting results. I'm wondering if this constraint you have — which on one hand might hold you back — is actually an advantage. At Shed, are you doing anything with personas? Does that impact how you try to acquire or reacquire customers?
Lance Dobson
This goes back a bit to the — I didn't say this a minute ago, but this is the 'meeting people where they are' concept, helping people feel understood. Persona-based marketing can certainly be useful, but I think it can become too high-resolution a proxy for addressing the problems people are actually encountering, versus helping them feel understood at the level of the problem and the solution. So can it be useful? Yes. But I think simply understanding the very specific problems people are encountering, and addressing them there, matters more. This is fascinating to me, actually — I go back and forth on hyper-personalization all the time, because it can look and feel like marketing's version of analysis paralysis. You're dicing it apart, dicing that apart, and you end up with a tree of hyper-personal—
Bryan Mahoney
Yeah. Yep.
Lance Dobson
—segments that may not actually help people feel understood, may not build a relationship, may not target people where you need to, to your point. So I like the idea of starting at the problem and the solution, and working outward from there, making the experience about that.
Bryan Mahoney
Yeah.
Lance Dobson
If I make it super linear — like, ad, landing page, conversion, full experience — the thing that seems to work is one that's hyper-focused on the problem-solution concept, and perhaps layers on persona-type things after. People can spin their wheels on personas a bit, because the persona may or may not be the right proxy for the problem, if that makes sense.
Bryan Mahoney
I see, yeah, that does make sense. There are two different lenses here — the acquisition lens and the retention lens. Ten years ago it was all about acquisition — 'retention, what's that?' You just keep acquiring customers because you have all this capital available. You've lived through both — at Shed, how do you split your time between acquiring new customers on a net-new brand and retaining the customers you've already acquired, maybe using your best customers to go beget other customers?
Lance Dobson
Sure.
Lance Dobson
I'd be willing to wager that at almost any company you step into, the number of people devoted to retention is at least four-to-one over acquisition — probably more. Within the marketing team specifically it might be pretty linear, but look at ops, customer service — all the people devoted to 'I need to keep you, I'm here to assist you because you're—'
Bryan Mahoney
Really? Okay.
Lance Dobson
—here' — it massively outweighs acquisition generally, with maybe a few rare exceptions. I can think of a few one-to-three-person shops that just exist to get someone in and make a purchase, and that's it. But most of the brands I've engaged with—
Bryan Mahoney
Or maybe you're making a lifetime purchase — like buying a mattress, where I don't need to talk to you again for ten years, or until I know you've bought a house.
Lance Dobson
You'll have one to three max paid-search and paid-media people, a couple of people who do SEO, maybe a couple of writers. Even at pretty large companies, you have a handful of acquisition people. Then you have an ops team, plus the email marketing team, plus the customer service team, plus, plus, plus — you just have so many people devoted to retention, even if they're not on the—
Bryan Mahoney
Okay.
Lance Dobson
—email and SMS team, they're augmenting those like crazy. So I still think retention is king in this particular domain.
Bryan Mahoney
I like that — you work so hard to get the customer, you might as well make them love you. That's kind of the name of the game. We haven't talked about AI yet, in the couple of minutes we have left. We've talked about trust, retention, the human component — and you're working in a highly regulated industry, so I imagine you have some constraints on leveraging AI. What role is AI playing for you right now, in either acquisition or retention? And if you fast-forward 18 months, what role do you see it playing, if any?
Lance Dobson
First of all, I love that we relegated AI to an afterthought — I've been to conferences where it takes up the first half of the whole thing. So, I think that—
Bryan Mahoney
Yeah, that's it. There's no oxygen left.
Lance Dobson
—AI is tricky to me, because in spite of all the tools and all the ways people talk about it, it's still mostly a one-to-three-trick pony as far as I'm concerned. It can help with coding like crazy, and that's a pretty big trick, I'm not going to deny that — I've replaced—
Bryan Mahoney
Yeah, fantastic at coding.
Lance Dobson
—just for my own analytical and light coding work, I've probably replaced one to three dev people just by using an AI chat tool. I'm not a fan of using it for content creation — I'll use it for ideation and content structuring, but I still employ writers, and I still want my content to be human-written. There may be cases, like certain educational materials, where it doesn't really matter if it's human-written, and I can see some benefit there. But in my conversations with so many people, it just isn't quite to the point where we need to be 'AI-centric' in the way Shopify said they were going to be about eight months ago. I like the framework Shopify came out with at their conference — essentially, if you need to hire for something new, you have to make the case—
Bryan Mahoney
—that AI can't do the job.
Lance Dobson
Exactly. I think that's a good framework, because it forces you to try AI first and see if it can do it. That's how my team works — we use it a lot, mostly as, 'give me instructions on how to use this tool,' which is immensely useful, or 'make some creative and let's see if it's useful,' or 'let me take that and enhance it,' or for coding. There are probably people screaming at their phones saying 'I use it for this and it's amazing' — fair enough, but it seems to drop off pretty quickly for us beyond that. I'm not fully convinced yet, except maybe in instances where people are using tools like n8n with true AI agents to feed in and process data — I'm thinking of something like Fyxer AI that does that with email inboxes, which is pretty rad. But those can get expensive if you don't know how to set them up, and you can burn through a whole bunch of tokens.
Bryan Mahoney
No, it's a great answer — it's really helpful for people to hear how others are actually using it. There's sometimes this fear of, 'I've been excited, but I've also been disappointed' — I don't want it to just spit out a bunch of content. I tune out right away when I can tell someone's copy-pasted something from ChatGPT and posted it straight to LinkedIn — that's not you, and I'm following you because I'm interested in what you think and what you have to say. So it's helpful to hear how the people behind these brands are actually leveraging the tools today, where it's working. It's encouraging to hear you say you're using it for efficiency, that you love it for ideation, as a thought partner, but you still want a human being as the final decider on what's good, because you want to establish that relationship with customers. It brings us back to where we started — the more things change, the more they stay the same. The brands that win are the ones that understand how to connect with their customers. If you can use these tools to get rid of the repetitive tasks and focus more on nailing the perfect message, or building an even better product, then everyone's winning and we're moving forward. But if it's just a race to replace jobs, I think we're missing the point. We've covered a lot of ground today — I really enjoyed it. Lance, thanks so much for joining me.
Lance Dobson
Yeah, thanks, Brian. It was a pleasure. Hope we can do it again.
Bryan Mahoney
Yeah, of course.