Arielle Jackson on Tech & Positioning

Arielle Jackson is the Marketing Expert in Residence at First Round Capital, where she advises early-stage startups on brand and positioning. She previously led product marketing at Google, launched hardware at Square, and headed marketing and communications at Cover, a mobile startup acquired by Twitter.

I start all these conversations with the same question, which I borrowed from a friend of mine who helps people tell their story. And it's such a big question. I use it, but because it's so big, I kind of overexplain it—the way that I'm doing now. Before I ask it, I want you to know that you're in total control. You can answer or not answer any way that you want to. It's impossible to make a mistake. The question is: Where do you come from?

All right, well, I come from LA. I was born and raised here. I'm back here now. So, it's kind of this full-circle thing. I grew up in a pretty normal, loving household in a very normal neighborhood in LA. I grew up in Palms.

My mom and dad are both Jewish people from New York who kind of did better than their parents did—they went to graduate school and, I think, surpassed the expectations of their parents, who had surpassed the expectations of theirs.

So, I grew up with a pediatrician dad and a therapist mom, which made for really interesting dinner conversations and a strong focus on education. We were doing fine by American standards. I’d call it middle-class, upper-middle-class. But I went to a very fancy, progressive private school. That was really important to my parents—they made a lot of life choices to send me and my sister there. It was really instrumental in my upbringing.

One of the reasons I moved back to LA about six years ago was to send my kids to that school.

Oh, how sweet.

Yeah, so my kids now go to that school. I have so much to say about that. One thread is my parents—Jewish New Yorkers who came to LA in the late '70s for my dad's residency at Children's Hospital LA and never left.

We have a loud, loving family that's all up in each other's business. Very classic New York, I think. And that felt really normal to me. I loved learning. I loved school. I kind of did a lot of everything.

Yeah.

There's so much to say about this whole upbringing thing.

I know, it's hard. There's a lot there, of course.

Yeah, and then I think the other part that I would just pull on is I also come from kind of a weird insider-outsider relationship to the tech world. I've worked in marketing and tech my whole career.

I thought I was going to be a psychologist. I did a master's in psychology but decided research wasn’t at the pace I wanted to move. Seven years of researching something that four people in the world cared about didn’t seem appealing.

So, I stopped after my master’s, didn’t do a PhD, and went to Google of all places—kind of did a hard pivot from psychology to Google in 2003. Cool. Well, I want to stay back in LA. As a young girl, do you have a recollection of what you wanted to be when you grew up?

Yes, I wanted to be an artist. I was always drawing, painting, and making books. My mom saved a lot of this stuff. I have books and books that I wrote and illustrated when I was little. I also loved to read and write. At some point, I became kind of argumentative. People would say I should be a lawyer, but I didn’t want to be a lawyer.

Yeah. And I’m curious about the school—you moved back for the school that you went to as a child. What was it like to encounter it as a parent?

Yeah, it's really interesting to come back to something where you’ve changed, but it's mostly still the same. It changed a little, of course—it’s bigger, has a nicer campus.

It's great. I love it there. I’m trying to find words to describe it really succinctly. It’s a place that’s really full of joy.

The way I experienced going to school—I still remember every teacher I had. Some of them are still there and remember me. Now they’re teaching my children.

Wow.

So, it’s pretty special.

I'm curious, because I grew up in the burbs in Western New York, and Los Angeles is always at least partially mythic. Do you know what I mean? So, what does it mean to you to be from LA? What is that like?

LA is such a big place. I spent 18 years here, then 18 years in San Francisco, and now I’m back in LA for a while. It’s so big that saying you’re from LA doesn’t really mean that much. If you grew up in the Valley or near the beach or somewhere else, you’d have a very different experience.

LA has a million tropes—it’s the butt of a lot of jokes, and all those things are somewhat true. But LA is just so big. There’s so much sprawl, so much culture, so much of everything. Probably the way New York City is, although more compact.

You can choose your own adventure and make it what you want. I live in Santa Monica now and don’t really leave Santa Monica very much. You have a very different experience if you’re in this little bubble of the world. The traffic’s so bad that I could either go to the East Side to visit a friend or make it to San Francisco in the same amount of time.

Yeah. So, catch us up—tell me, where are you now? What are you doing for work? What are your days like?

Yeah, so now I work as the—it's a really silly title—but the marketing expert in residence at First Round Capital, which is a seed-stage venture fund that invests in founders often when all they have is an idea.

We like to think of it as the "imagine if" stage of company building. My job is to help founders—usually pre-product and pre-launch—figure out how to talk about what they're doing in a way that resonates with customers.

Larger brands spend a lot of time on that. We try to do a quick-and-dirty version that fits where these founders are, so they’re set up to find product-market fit faster—or pivot, if it’s not the right thing.

Yeah. I’m curious—you pointed at the title. You seem to have a conflicted relationship with it. I quite like it. Can you tell me more about it? Maybe the story of why you feel the way you do about it?

Yeah. So, First Round—I’ve been working there for over 10 years. When I first started, it was an experiment. I had been the marketing person at a company that had been funded by First Round. That company was acquired by Twitter. I decided not to go to Twitter with the rest of the team and started emailing people I’d worked with at Square, Google, and other places, saying, “Hey, I didn’t go to Twitter. I’m ready to help you. If you need marketing help, let me know.”

That was my foray into freelance world. It just so happened that First Round didn’t have a platform team—kind of the people who help post-investment with companies. They were just starting to think about that. Long story short, I did this experiment where, for three months, they were one of my clients. I spent one day a week in their office, helping their founders and seeing if I could do some of the work I used to do as an in-house marketer—but in a more consultative way.

I think that's where the title comes in and why I find it kind of weird. It sounds very transient to me. "In residence" usually implies you’re doing something for a year while figuring out your next full-time move—like starting a company, joining a company, or becoming an investor. Ten years in, I’m still “in residence,” and that just seems funny. And also, the word "expert" is weird. Are there really experts anymore? It feels strange to call yourself that.

How would you describe the relationship between—well, there’s a lot packed in here—technology and marketing, the culture of tech businesses and their relationship with marketing, and then how venture capital views it. The name of your role seems to reflect a bit of that tension, or confusion, maybe. Or maybe I’m projecting.

Never thought about it like that.

Maybe I’m making that up. Okay. I think there are three questions in there: technology and marketing, venture capital and marketing, and then maybe the intersection of the two. Is that fair?

It comes from this place of—well, I invited you here because you had highlighted Jesse Caesar’s work in qualitative research. You’re someone I see as an advocate for principles I align with. And you’re operating in environments that, while not hostile to those principles, don’t exactly feel native to them. So I wonder what it's like for you—being a marketer inside a venture fund, in tech culture. And maybe I’m just exposing all my prejudices.

No, I think a lot of those prejudices are right.

Technology—this comes from so many tech people believing that if you build a good product, people will come. We don’t need to do marketing. If we just build something great, people will want it. That’s the marketing—the product is the marketing.

I started my career at Google, and that was kind of the ethos. But what they really meant was advertising. As in, "We don’t advertise." But marketing isn’t just advertising. Marketing is figuring out what to build, how to talk about it, making sure the right people hear about it, and ensuring it solves a problem and means something to them.

I think the allergy that the tech industry has to marketing is more about not wanting to advertise. You’ll hear founders in interviews say things like, "We did no marketing and grew by X." But when you look into it, they did so much marketing. It's just this kind of posturing—especially from people with engineering or product backgrounds—where they say marketing doesn’t matter. But it actually matters quite a bit.

With the founders I work with, they often equate marketing with advertising, and they don’t want to do that yet. So we focus on all the other things that will help them reach the people who have a need that their product can meet.

Yeah. How—oh, go ahead.

No, you go.

No, you had more to say.

Oh, I was just going to say: in some ways, I feel like an advocate for really fundamental, basic stuff. The kind of thing anyone who works in qualitative research, brand strategy, or communications takes for granted. It's like the air we breathe—but not for everyone.

Yeah.

So things like: when you say everything, it’s not clear what you’re saying. What are you saying first? What are you saying second? That’s part of marketing. Or understanding the competing alternative you’re up against—who can be your "bad guy" when you're storytelling. Those things feel basic to us, but if you grew up learning to write code or build product, they’re not so obvious.

How would you say that’s changed—the role of marketing or fluency with these concepts—during your time?

Honestly, I don’t think it’s changed as much as the rest of technology has. The fundamentals of marketing—understanding your user, understanding the magic of what you’re bringing into the world, and connecting the two—have always been what it’s about. That’s the part of marketing that excites me.

What has changed, especially in the last two years, are all the AI tools. Everyone thinks they’ll change how the work is done and who can do it. And there are real changes happening, but they’re recent. I think the fundamentals still apply, no matter what.

That’s what gets me excited—understanding what makes people tick, understanding the real magic of a product, who it’s for, why they should care—and making that so clear that what makes it unique truly stands out.

Yeah. What do you love about the work? Like, where's the joy in it for you?

I think it's twofold. One is connecting the magic. Early in my career, someone taught me about positioning—about understanding the essence of something and then finding the language to describe it so that it resonates with the right people. That often starts with understanding the people first, building something that meets their needs, and then describing the magic to them.

Some of it is that process, which is a mix of sleuthing, uncovering, talking to people, and figuring out what makes something different. And then it’s almost like an act of sacrifice: what can we let go of—the things we don’t need to say, the table stakes, the things users don’t care about, or the things everyone says—so we can focus on the one thing that is the magic. I get really excited when we figure that out. It feels like a light bulb moment.

I also get excited about the people aspect of this job. Some part of me finds it a little therapeutic. I do a lot of one-on-one meetings and conversations like this—talking with founders, getting into their motivations, their origin stories. You start to pull out their passion. I’ve had people cry. It feels really human.

So, the combination of the aha moments, the human connection, and the variety. I usually work with about eight companies at a time—everything from vertical AI to skincare, to consumer hardware, to healthcare. It’s all over the place. It’s fun to know a little bit about a lot of things.

Yeah. I’m curious—I’ve got two questions, which is always dangerous. First: when do they call you? I imagine a red phone at First Round. When do they pick it up?

Yeah. So, who is “they”?

Right—good question.

There are two answers. Let me tell you the most common, and then the occasional. Most of the time, it's right after we invest in a company. We’re often the first money in—usually between one and ten million dollars. That’s the first big check these founders are getting to start and grow their business.

As part of that, there’s been a lot of diligence and getting-to-know-you between the partner leading the investment and the founder. So, when they onboard to First Round, we usually already know, “Okay, these folks are going to need help with positioning. They’re going to need a new name. They want to launch soon.”

We’ll have an onboarding call and figure out what to help them with first. So it's usually very early—day two kind of thing. Sometimes, I’ll even talk to them before the check closes, just to get started.

Sometimes, the help we provide—not just marketing, but support from our other experts—is one of the reasons people choose First Round. It’s not the reason, but one of them.

One of my side projects has been figuring out how to tell First Round’s story. I recently redid the entire First Round website. Venture capital is such a commodity, so figuring out what really makes us different was fun and interesting. We hadn’t done it in ten years. It was a big refresh and a collaborative effort.

But the idea is: one of the things that makes First Round different is we do the work with you. It’s not just, “Here’s someone who can help,” or, “You’ll be fine,” or, “Here’s some advice.” It’s not armchair quarterbacking.

We get in there. We’re in the Google Doc with you. We’re on the customer calls with you. We’re really in it with the founders—almost like an extension of their team until they build their own. Eventually, hopefully, they hire a marketer. I’ll help interview them, and then I’ll work myself out of a job.

Yeah. I’m just curious—when you sit down for that first meeting, maybe even before the check is closed—what are you thinking about? How do you approach that conversation? What are you looking for? What kinds of questions do you ask? I’m just so interested in how you engage in that first moment, how you create a conversation.

Yeah. So, I start by trying to get a little educated about the company so I’m not going in totally cold. I’ll read their investor deck, their website—if they have one. Just a very cursory look. Often, there isn’t much yet.

If it’s an industry I’ve worked in before—like all humans—I relate the unknown to what I already know, and try to fill in the gaps from there. If it’s something I know nothing about—like this week, I’m working with a company in the freight trucking space—there’s a lot of lingo, and I have no background in it. But I’ve worked on other marketplaces, so I’ll bring in what I know and get up to speed quickly. That first conversation is very diagnostic.

It's like, where are you? What do you need help with? Is this even the right time for me to help you? What do you know? What do you not know? Then I walk them through a menu of things I could help with.

The repeatable pattern I see with almost all founders is they need help with positioning, messaging, brand identity, a website, and eventually a launch. Those things don't always start right after that first meeting, but that's the usual sequence.

Yeah. And how do you talk about positioning with them? I'm always fascinated by how people communicate, especially around first principles. I'm curious—do you have ways of explaining it that help people with no experience in this world? How do you help them understand why this stuff matters?

Yeah. Often, the first meeting is them talking at me for 30 minutes, telling me about their business—what they do today, and where they're going. And then I say, "Cool, so if you had to give me the 30-second version of that, what would you say?" They usually stumble. And that’s when I explain, “That’s what we’re going to work on.”

Oh, wow.

They know their business; they just don’t have a succinct way of describing it. So our work becomes that process of excavation and sacrifice to get them to a place where I can say: “Company X is a Y that does Z for [customer segment].” Make it the truth, but make it the truth that sounds good.

Yeah. I love that you give them the experience of trying—and failing—so they feel the gap.

I believe in that a lot. I also have some worksheets I give them. If I sense they need help distilling their message after that first conversation, I send them an article and a worksheet.

The worksheet is really simple: Who’s your target customer? What’s their problem? What are they doing today to solve that problem? How do they feel about that? Just basic questions.

I always ask them to take a first pass on it on their own—homework before we engage. Then I have something to work from, and I can gauge whether this needs 10% refinement or if we really need to go talk to some customers.

I believe in having them do it once themselves. That way they can see the difference: “I was here, and then we did three or four or five workshops, and now I’m here.” They feel better. They can see how their website will come to life.

Yeah. You were at Google for a while. Do you have other stories from those experiences—working with these giants—that you still carry with you? I feel like you were involved in some monumental projects and product launches. What did you learn through those?

Yeah, that’s a big question. When I joined Google, there were just over a thousand people. So it was already big, but it felt small.

Part of that was because there were maybe eight or ten people in marketing—maybe twelve. It was small. I learned so much. Google from 2003 to 2010 was awesome. When you ask where I come from, a lot of what I learned there I thought was normal, but it was actually just company excellence.

I didn’t know any different—that was my first real job. I’d worked since I was 15, but that was my first job at a company. Google did a lot of things right. Some of them I think they still do right. I left in 2011, so my experience is a bit outdated, but it was a rocket ship.

You got to be a smart, young person with potential, and you were given great managers, mentors, and responsibilities—probably more than you should have had. You just kept proving yourself and getting more.

The people and the early culture were really excellent. And it came from things I took for granted at the time but now realize were special—like having a purpose statement you knew before you even started.

Everyone could recite: “To organize the world’s information and make it universally accessible and useful.” You understood the work you were doing and how it connected to that purpose. That’s rare. It seems so obvious—why don’t more companies do that?

Yeah, that’s beautiful. I’m curious—you mentioned you just refreshed First Round’s messaging. Is that the right way to put it?

Yes. We refreshed our messaging.

Refreshed your messaging. What did you learn about venture capital? What's the state of the category that you addressed? I'm curious about that experience and what you learned.

I mean, you're constantly addressing where you fall within a category when you offer a product in that category. First Round, twenty years ago, was really the first seed-stage investor that focused on companies at a very early stage. But over the last twenty years, the category has grown significantly.

Now there are angels, pre-seed investors—it's gone even earlier than seed. There are so many general partners a founder could raise money from: individuals writing checks, semi-angel funds, pre-seed funds, seed-stage funds, multi-stage funds. Even the big multi-stage investors are writing seed checks now. You can raise a seed round from a firm that also writes Series C or growth-stage checks.

What’s unique about First Round is that we’ve always focused solely on the seed stage. That’s all we do. So when we talk about sacrifice—it means we’ve chosen to only support this phase of company building, from the very beginning through the first two years.

First Round has done that across a huge variety of industries—consumer, B2B, healthcare, AI—but it’s always that early stage. And it’s rare to find that combination: deep focus and a full set of services tailored to help founders at that moment.

You can get money from firms that focus on seed but don’t offer much support, or from firms that invest across stages but don’t really care about the seed phase. They treat it more like an option: “If I invest $5 million now, maybe I’ll invest $100 million later.” But you're not important to them until you're big.

Yeah.

So part of our job in this messaging refresh was communicating that, and also this idea that we do the work with you. We used to say, “We’re called First Round for a reason”—that was the line on our website.

We changed it through this process of talking to lots of people: founders, employees, people who took our money, people who didn’t, those who worked closely with us and those who didn’t. We came up with the new line: Where imagine if gets to work.

That’s now the core of the website. We take your “imagine if”—and we wrote an "imagine if" statement for every company we've invested in. If you go to the site, the companies page is made up of those statements.

I actually tried to use AI to write those, with my colleague Jesse—not Jesse Caesar, a different Jesse who works at First Round. Unfortunately, that didn’t work very well. So, we wrote them all by hand—for hundreds of companies.

But the idea is: you have this “imagine if,” but it's only as good as what you do with it. And we’ll fill in for you—support you—until you’ve built the team to carry that forward.

Wow. What is the role of research—qualitative or otherwise? How do you go about learning? When does research show up in your work?

A lot of the work I do with First Round founders involves secondhand research—meaning, the founder is doing the actual research. We believe the founder should be the one talking to potential customers—doing the calls, the interviews, gathering insights from their target audience to understand what people need.

We have a program called PMF Method—Product Market Fit Method—where we teach founders how to do high-quality customer discovery, especially with a focus on revenue. We call it dollar-driven discovery: will people actually pay for this? That’s especially important in B2B.

My ability to do my job—especially positioning—depends on the founder’s understanding of their customer. If they don’t understand their customer and can’t communicate that to me, then I can’t do my part. In those cases, we go out and talk to customers ourselves before we can do any real positioning work.

That said, I usually rely on founders to do this work just because of the volume—I'm working with eight companies at a time, and they’re rotating every six weeks. I can’t do the research justice in that format.

Outside of First Round, when I do consulting, I get more involved in primary research. I often include qualitative work—sometimes I do it myself, sometimes I bring someone in. But the principle is the same: start with the customer. What’s working? What’s not? How do customers understand you—or not? How do non-customers perceive you? That’s always the foundation of good messaging.

Yeah. Again, I'm curious. Oh my God, the question just vacated my mind. Oh—the product-market fit method. What can you share about how that informs the qualitative side of things?

So that program is for founders who are even earlier than the ones we typically write seed-stage checks for. Often, they don’t even have a clear “imagine if”—they're still just thinking through an idea.

The first step when you don’t have a solid hypothesis is to make one—and then go test it. A lot of that program is about validating that a real problem exists, validating that there's a specific persona who has that problem, and validating that you have a promise which, if fulfilled in your chosen market, could support a venture-scale business.

Sometimes it starts with a founder saying, “I have this unique insight into the world,” either from a past experience or from going unreasonably deep to learn something.

It could be, “Oh, there’s this security gap—I used to work at a security company, and I see a new way to solve it.” Then it’s like: Who is it for? What’s their problem? What’s the promise you can make to them? And is the market big enough to support a venture-backed business?

There are steps for all of that, and we think of it in levels. The first major milestone is: can you get five really, really happy customers? Build something and get five truly happy users. That’s a big step. If you can’t get five people who are thrilled, then one of the elements—product, promise, persona, or problem—is off. From there, you adjust.

What kinds of conversations do you have with founders around their understanding of customers? How open are they to the idea of research?

They’re generally very open. Sometimes they just need help structuring how to do it. Founders need this skill—they need to be able to talk to people and understand their problems. If they don’t have that skill, we help them build it. And in some cases, we’ll do it for them—we’ll go talk to ten potential customers and come back with insights.

What is the skill? How would you describe it?

It’s the basic stuff of qualitative research: asking non-leading questions, digging into “why” without using the word why, finding the thought behind the thought. If someone’s unclear, you reframe the question until it lands. It’s basic—but foundational. Stuff that, for you, is like air and water.

Yeah. But I love making that explicit. The way you casually listed those principles—that’s so cool. I don’t think enough people ever encounter them laid out like that. Well, tell me what you think about this—and I’m interrupting your response, sorry—but I often feel that qualitative research is invisible when done well. You can watch someone doing an incredible job applying all those principles and not even realize they’re doing anything beyond being friendly. That’s why I loved how casually you laid those ideas out.

Yeah. I mean, that’s mastery. I don’t know that any of our founders get to that level of proficiency.

What comes to mind is the founder who thinks they’ve done customer discovery because they pitched their product to ten people and asked what they thought. And those ten people said, “Yeah, seems pretty good. Come back when you have something.”

Then the founder walks away thinking, There’s something here, I should build this. But “Come back when you have a product” isn’t a strong signal. The response you actually want is, “Oh my gosh, when can I sign up? This is amazing.”

A lot of it is shifting from pitch mode into discovery mode—uncovering problems, understanding how people have tried to solve them, learning where the budget lives, and getting smarter so you can build something better. Then, when you return with that better product, people say, “Oh my God, it does that? When can I sign up?” That’s the reaction you’re aiming for.

I remember early in my career, I did a lot of validation work—lots of different types of projects with Unilever. One of them was for Lipton Cup of Soup. I think they were re-engineering it somehow. The line that stuck from that project was, “It would be great for camping.” How do you feel about the new Lipton Cup of Soup? “It would be great for camping.”

Like—no thank you, kind of, right? Yeah. When you asked, "Where do I come from?" I didn’t mention this, but I’ve pretty much always been in tech in various ways.

One of the reasons I still sing Google's praises from the early days is that while I was there, I did an exchange program with Procter & Gamble to go through their Associate Brand Manager training. That was so awesome—an amazing experience.

I relate it to Paul and my experience there. At Google, a lot of our research was user testing: you’d have people click around while you sat behind the glass. You could test messaging that way too, but it was mostly UX.

At Procter & Gamble, it was so different—and so cool. I got to do a Febreze shop-along. And I learned from the guy who did the Old Spice campaign that blew up in 2007. He had also been the brand manager for Tampax, and we talked about Tampax Pearl.

It was such a great crash course in excellent qualitative research and in brands built entirely on customer insight. In those cases, there's some product differentiation, sure—but the brand is 90% of it. In tech, I think that ratio is flipped. The product is a much bigger part of the value, and brand is more like the icing on the cake. But it’s not just icing on the cake.

Yes. I feel so vindicated that we’ve uncovered this P&G moment. I was always curious—do you feel like you carry what you learned at P&G with you? Does it help in the work you do now? I think that’s really amazing. How impactful would you say that was on how you think about marketing and your work now?

I think that organization is run by marketers in a way most tech companies are not. A tech company is usually run by an engineer or a product person. I had this friend I worked with—he was the product manager for Gmail when I was the marketing manager. His name’s Keith Coleman. He now runs Twitter’s Community Notes feature.

Oh wow, wow.

Anyway, he used to say: “Product’s job is to make the boat. Your job is to paint the boat yellow and let it sail.” That’s how he saw it. And there was a fun tension in that. In some ways, it was like, yeah—tell me what the product does and let me paint the boat yellow.

We had a lot of fun painting different parts of Gmail yellow and letting it fly. We got to do cool stuff with Gmail’s marketing early on that now sounds kind of blasé, but at the time it was amazing—collaborative YouTube videos, stuff like that.

I’m talking 2007, 2008, 2009. We did all kinds of crazy stuff. We made keyboard shortcut stickers for our biggest users and mailed them out. You had to send us a self-addressed stamped envelope to get them. It was very community marketing—before that was even a thing.

So we had a lot of fun painting the boat yellow, but my experience at P&G taught me that it’s not just about painting the boat yellow. It’s about figuring out how to build the boat in the first place. And that’s how P&G does it.

Yeah. I’m so excited we uncovered that. I feel like I sensed some unnatural wisdom in you—especially for someone operating in tech. But again, that’s my own bias. I feel like in the tech world, especially with lean startup culture, qualitative research is often treated in a very mechanical way. It has different objectives and feels like it approaches the experience so differently from how I learned. Does that resonate with you? I mean, I’m letting my bias show.

Well, I think there is an ethos in tech—it’s very much the “users don’t know what they want” thing. Don’t ask them. They’ll ask for a faster horse. Build it and they’ll come. Move fast and break things. Throw spaghetti at the wall.

That’s a big part of the tech mindset. And yeah, some of it is true. But there are also people who build products really thoughtfully and have a natural tendency to bring in the customer voice early. It’s just the exception—not the rule. At a place like Procter & Gamble, it’s the rule. It’s codified. It’s what you do.

Yeah, yeah. And I think for me, my experience was mostly just feeling left out of these organizations that were being built a different way—these brands that were being built a different way. You know what I mean?

I don't think it's wrong, though, in a lot of ways. If you think about a product like air freshener—which was my follow-me-home, shop-along project for Febreze, some kind of new form factor—I don’t remember the exact details, but that’s a commodity product, right?

The insight that brand was built on, and I remember this really clearly, was that people didn’t use Febreze to mask bad smells. They used it to signify that their home had been cleaned and was ready. That was the insight: "I just finished deep cleaning, and now I’ll spray Febreze as a sign that my home is clean." It wasn’t about spraying to fix something that smelled bad—it was a signal.

That was a deep insight. They had whole campaigns—probably even Super Bowl ads—based on that. And it was really cool, but they needed that kind of insight because the product itself, in isolation, was just a nice-smelling spray.

Whereas in tech, sometimes the product is so fundamentally different—something you couldn’t have done before—that marketing’s job is just to clearly explain what it does. You don’t necessarily need a super deep insight if the product is already mind-blowing. It's just, “Wow, you couldn’t do this before. Now you can.”

Yeah. I remember—maybe this was a colleague of yours—I always reference an article about Gmail positioning, this idea of “discoverable benefits,” like “come for X, stay for Y.” Does that ring a bell?

Yeah, that vaguely rings a bell. The Gmail positioning story is kind of interesting because it launched publicly on April 1st—April Fool’s Day—and we said, “We’re giving everyone a gig of storage,” and people thought it was a joke.

Oh, wow. Really?

Yeah. It sounded too good to be true. A gig of storage at the time was insane.

Yeah. That was probably a whole new metric, right? Had anyone had a gig of anything?

Yeah, exactly. The idea that you got a gig was mind-blowing—and it was a message that could spread. People were saying, “Did you hear Gmail gives you a gig of storage?” People were buying invites on eBay. It became this whole thing once people realized it was real.

All the messaging was about: “You can search your email because you have a gig, and we’re Google, and we’re good at search. You never have to delete a message again.” That was the primary hook. Then there were sub-messages: “It’s fast,” “There’s no spam,” and so on. But those weren’t why you came. They were why you stayed.

And I think a lot of products are like that. What’s the hook? Especially in tech, where it’s so easy to try something—and just as easy to abandon it. What’s the thing that makes someone try it? What’s the thing that makes them stick? The marketable benefit is usually the differentiator—the “wow” thing that makes you tell your friends. The retention benefit is what keeps you coming back.

Yeah. Yeah, it’s awesome. I totally agree—there’s no right or wrong. I think I was just being territorial and prideful about my consumer qualitative background. How would you say the role of research has changed over the time you’ve been working? Has it changed at all?

I think it’s similar to what we were saying about how marketing has changed. The fundamentals haven’t really changed. The tools might have.

For example, it used to be hard to go find the user persona you needed—say, people who run hedge funds, or women looking for fertility services. Conducting those interviews used to be really hard. But now, with Zoom, it’s so much easier to recruit and run them. There’s less excuse not to do it.

More recently, there’s been interest in things like synthetic users, which I haven’t fully bought into yet. But they can give you a good first pass.

I was working on something recently where I needed to understand a “day in the life” of a veterinarian. I just needed to know: What do they do? How much money do they make? What are they worried about? Who employs them? What are their incentives? What's the business model?

AI made it really easy to get that basic, high-level understanding. But I still believe that real, face-to-face conversations give you a much deeper understanding—just like they did 20 years ago.

Yeah, that’s funny. This is a bit of a tangent, but I’ve had conversations with people in the political world who are questioning how they’ve been learning. They’re so tied to polling and surveys and are starting to open up to richer, deeper qualitative methods—like ethnography—which we would take for granted.

Have you seen a shift toward ethnography or deeper qual approaches? You mentioned changes in tools—has there been a shift in the types of tools people are choosing? And I definitely want to talk more about synthetic users because I find that fascinating.

Yeah, I don’t think there’s a ton of ethnography happening with the founders I work with. I think there's some good one-on-one qual being done. Sometimes it's basic, but sufficient. And then there are times where it's very basic and not sufficient at all.

Part of my job is to say, “I don’t think you understand this user well enough.” I’ll give you an example. I’m working with a very early-stage founder who is trying to be everything for everyone—hasn’t really chosen a clear direction. The mindset is, “Anyone who does this can use it.”

But the reality is there are ten other companies going after that same broad market. One way to win is to lean into the features and benefits that apply to a subset of that market—where you’re uniquely strong. So, we’re pushing this founder to niche down, to narrow the audience. That way, the things they’ve built will really shine.

It’s hard for her, because she’s essentially saying, “I’m going to sacrifice some of my current users.” She’ll still keep them, but she won’t go after more of them. She’s shifting to fewer, higher-value deals, where her product will be stickier.

That’s a tough move—but when she went back and talked to those customers, she realized, “Wow, these people see me as the best-fit product.” For everyone else, there are lots of other tools that could meet their needs. That understanding came from those customer conversations.

She had that experience. As you were talking, it reminded me of my own—taking out new concepts and products. You know very clearly when something clicks with someone—or doesn’t. When it doesn’t, you struggle. But then you find that one person who gets it, and it’s like, “Oh my God, here we go.” The sun is shining, the sky opens up—it’s a real moment.

Yeah. I mean, we’re still in process with that founder, but she’s definitely had glimpses of that experience. And like we were saying earlier—you can’t always ask, “Why do you do that?” But you can get to the why behind the why.

My own career went from Google to Square to a very tiny startup. I kept going smaller and smaller. The last company I worked at had seven people. It was a seed-stage company building an Android app. This was around 2012–2013.

At the time, Android was totally underserved. This was before usertesting.com and tools like that. So, the research we did was: we posted an ad on Craigslist—I'm sure you’ve done this too—saying, “Do you have an Android phone? Meet us at a Starbucks and talk to us for 10 minutes. We’ll give you a $20 gift card.”

We did this all around the Bay Area—Oakland, Palo Alto, San Francisco. That research made the company, I have to say. The first part of the interview was just: “Show me your phone. What apps do you use? Where did you get that phone? How did you choose it?” The second part was mockups—getting them to react to prompts and possible app store designs.

The insight we got was powerful. It wasn’t just about how to position the product. What we learned—though no one ever said it explicitly—was that people felt kind of ashamed of their Android phones.

They’d say things like, “Yeah, it kind of sucks,” or “I got it because it was cheaper,” or “Yeah, I know it’s not great.” You could sense the shame. So, we leaned into that. We positioned ourselves as an Android-only company: “We’re building an app you can only get on Android, because iPhone doesn’t let you do this. But Android does.”

That shift—owning the platform and making users feel proud of it—was a game-changer. All of a sudden, they were like, “I’m not ashamed of my phone anymore. My phone’s cool. It can do cool stuff.” And tapping into that emotional ethos—that’s when the product really took off.

Wow.

That whole experience of sitting in those Starbucks—again, it wasn’t perfect research. We only did it in the Bay Area. There were a lot of flaws. But it was enough.

Yeah. How do you describe what happened? What did that kind of face-to-face qual actually do for you—what only that kind of interaction can do for a team?

It gave us real confidence in how to talk about the product—both from a features and benefits perspective, and from the “your iPhone can’t do this” angle.It validated assumptions we had, and it just felt like, “Yeah, I’ve talked to 20 people—and if 20 people all tell you the same thing, you don’t need to talk to 20 more.” You know what I mean? Like—we’re good. Yeah, we’re good.

Beautiful. Well, listen, I want to thank you so much. This hour has flown by. I really appreciate you accepting the invitation and sharing your experience. It was really great.

Thank you so much. Thanks—I feel like we could keep talking for another hour. I looked up and thought, “Wow, it’s already been an hour.”

I know, it’s true. I’ve got a bunch more questions, but I just checked and we are at time. So—maybe another time.

Lovely. Thank you, Peter.

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