Joining Wealthfront

Alex Kracov: So I'd love to start today's conversation with your time at Wealthfront where you were a marketing director responsible for product and brand. I'd love to know what made you join Wealthfront. What was it like when you joined?

Maya Spivak: Oh, man. When I joined Wealthfront, there were 23 other people. So I was number 24. I joined because I deeply loved the product. I loved the product for years before I joined the actual company. I was one of those people that was a very noisy customer, where I would send in my thoughts and my feedback. It helped that I actually lived in Palo Alto at the time, because Wealthfront was based in Palo Alto. I was born in Palo Alto.

I, one day, walked past a building which had a sign in the window. Literally, one of those cardboard. Not cardboard but Styrofoam board sign. On the front was printed the first Wealthfront logo. It was literally propped in the window. After I saw that, I was like, whoa, this is the Wealthfront building. Then I went back and emailed them. I was like, "Hey, I'm a customer. I love the product. By the way, I live in Palo Alto. Did you know that if you have customers that maybe live in Palo Alto - which probably have a good handful because we're all tech people - and they walk past this location, and they see this styrofoam board in the window, they might not think the brand is super legit, and it's safe to park your money there and invest in an automated fashion. Maybe that thought might cross their mind." That's when we connected, based on that light and good intention feedback. They were probably a little bit offended. But in general, that made the connection between me, a very enthusiastic customer, and them, very enthusiastic founders. We were exchanging exchanging notes for probably about a year before they asked me to join just as a marketer. I'm exchanging notes like I was an alpha user of basically everything. It's like, "Hey, we're about to announce this. What do you think?" And I would just send back some notes.

Alex Kracov: Very cool. I know one of the founders of Wealthfront was Andy Rachleff, who, I guess, was a Benchmark partner and had a big career before Wealthfront. He came up with the idea. So it sounds like you were trading notes with him directly. Was he the one who had hire you, or was it someone else? I'm curious. When you did join, what was your first goals as a marketing director?

Maya Spivak: Yeah, he's definitely one of the people. He took me out for a cookie. He bought me a cookie. Well, I was working at Google at the time. And so we picked a nearby cafe to meet and hang out. He told me more about himself and why he founded Wealthfront and his belief and his vision. He bought me a cookie at Specialty's, and I'll never forget that. So that was part of our conversation. That was like, I definitely need to work for this man. He's incredible.

When I first joined, what we had to do was basically just open up beyond word-of-mouth marketing. So at 24 people, Wealthfront had - I don't remember how many assets under management we have, how much money. That's the metric by which FinTech institutions, banks or retail banks assess their success. It's like how much money they actually have under management. It's called assets under management (AUM). I don't remember how much the AUM was, but it was well under $500 million. That was all word of mouth, just people in Silicon Valley who knew about what Wealthfront was trying to build and telling each other about it. What we needed to do when Wealthfront decided to open up marketing as a function was to get out to the broader world or even just penetrate Silicon Valley more. In the very beginning, what we were selling was an automated investment service, but we had a pretty high bar for a new customer to hurdle over in advance of being able to even open an account.

So in the very beginning, Wealthfront was automated investment services for accounts that were a minimum of $5,000. So it's like a non-trivial amount of money that you had to be ready to lock up into a long-term investment strategy. You had to know what a long-term investment strategy was, and you had to be interested in the long-term investment strategy. And so those three things, that was the start of the marketing. It's like, how do I explain to people? How do we explain to people what's the difference between long-term passive investing and the kind of investing that people tend to think about when they first hear the word investing, which is like, that's more of the Wolf of Wall Street type of investing. That's like the day trading type of situation. That's the beat the market Jim Cramer type of test pounding investing. That's what people tend to think about. That's pretty much the opposite of what Wealthfront does. There's a lot of education, just a ton of product education, leaning on expertise that we had in-house and really lifting up some of the incredible authorities on the topic that we were working with like Burt Malkiel, who was our Chief Investment Officer and literally wrote the book called A Random Walk Down Wall Street, the primer on why you should be passively investing for the long term. That was basically the entire first two years. It was elevating all of that, teaching people.

Marketing at Wealthfront

Alex Kracov: It sounds like a lot of that education and sort of building trust in the market, it was mostly content marketing. Because I imagine automated investing and long-term investing, the stuff are scary concepts for a lot of people. So was it mostly content marketing of how you pushed that message, or was there other things that you were doing as well?

Maya Spivak: Both of those things. So it was mostly content marketing, but there was a lot of product marketing involved. The difference between those two, I would say, probably comes down to the channels in which you create those materials for. The Wealthfront blog, for example, was probably the thing that we held up most on a pedestal. It's just incredible knowledge from really trustworthy experts, written in a way that we sought to educate people. Some of it wasn't even about things you could do with Wealthfront. It was just like you know you can trust the people that built Wealthfront because they're writing and telling you about your equity plan at your startup that you work at. Because the majority of our early day customers were engineers and tech people in Silicon Valley, because they were the ones in the earliest days who trusted that machines can do a lot of things better than humans can, including investing money. This was a key. There's a foundational philosophy you had to believe in.

The Wealthfront blog was our content marketing engine, even though we weren't just writing about investing, investing, investing in there. We were writing off of the themes investing, like investing in yourself, investing in your career, what is equity, how do RSUs work, how do preferred stock options work and all this kind of stuff. You can't put your stock options inside of Wealthfront. You still can't to this day, but we were teaching and we were engendering trust.

Then on the flip side of the product marketing where we actually work, explaining what the product does and what the features are, every time we rolled out a new service, the component marketing pieces that involved a lot of creativity to make them mainstream consumer could pick up and to learn from. So that was, for example, Wealthfront was the first automated investment service to debut tax-loss harvesting and then the first to do direct indexing, which is an even more sophisticated financial technique that we automated. And so people that do these sophisticated investing technique in the real world, pre-app and pre-services that do it using machines, they don't even know how to explain it. So we have to figure out how to explain the concept in general. We have to figure out how to explain the concept in general as it is practiced by machines in the software and algorithm. Then we have to do it in a way that engenders trust because this was pre-AI. It's okay to let the machine do your work for you. Actually, that guy, that wolf on Wall Street who your parents know, or your uncle, or your aunt has the hook up for, you don't need that guy. What you need is a trustworthy automated solution like Wealthfront. So there's a lot of I think product marketing, which I would really distinctly put in its own corner, away from the blog and the content marketing that we were doing.

Launching Wealthfront Products

Alex Kracov: Let's go a level deeper on the product launches, because you mentioned a few that you had launched at Wealthfront like the index investing. I think you also did the first mobile app for iOS and some others. Were any of those product launches super memorable? Can you take us behind the scenes of an actual product launch? Because there's a lot of understanding. Okay. You do work on Wall Street before this. What is this thing that they're actually building, turning that into marketing messaging, making all the collateral? What did that actually look like at Wealthfront?

Maya Spivak: Yeah, it was really fun. For example, for the launch of tax-loss harvesting, this was the first time that we decided to do a video. We decided to do an animation, an animated cartoon. So this was approaching eight years ago. The cartoon, the animation, in order to translate a complicated financial technique into an animated, very, very short film like an explainer video, you have to first understand the concept so well that you then translate it to the designers and the animators who are making your video. You have to think up the analogy. What is the analogy for tax-loss harvesting? It's like you have to do something to make it visual. Because you can't just write tax-loss harvesting in fancy fonts and put some colors on there and that's your explainer. No, that doesn't explain anything.

We figured out this analogy where you're planting seeds and they grow, but certain once of your trees don't grow. In fact, they stay rooted. You can rip them out, rip your losses out. You harvest those losses. And so it's just this whole complicated but get a bull analogy, like way more artistic and interesting and definitely intellectual exercise. You get to see that whole thing come to life. As a marketer, you are first yourself. Like you mentioned, I didn't come from investment banking, and I didn't study it. I had Finance 101 in college, and that's where I really started to like it on a personal level, to like it enough to want to do it for myself and study it a little bit more personally. That's why I became a customer of Wealthfront when I first read about it. But I didn't have the education required. So you have to go so deep that you get it. Then you have to turn around and teach other people, because they have to get it in order to illustrate your concept. Then you get all the way to this finished explainer video, and people watch it. And it makes sense.

The best thing about the video when you tell stories with video and when you use those videos to explain concepts, the way that you know that it works in the world of marketing, in the world of tech marketing - maybe I don't want to over generalize and say that this always works, and that's how you know. But for me, in my career so far, I take it as a huge success when on launch day, the video that you created gets embedded in the assets created by other people. The journalist is writing up the story about you, your company, your launch, the thing that you debuted that day, and they willfully choose to embed your assets in their work. You know you did a good job, because they are very allergic to - journalists are allergic to anything that seems like itself too hard. They don't want to inject any more advertising into their difficult-to-read websites as they already are.

But if they choose to embed your assets, it's like win, win, win, win, win. Everybody wins. Then years later, I'm still Googling these articles so that I can show my prior work as it is held up and endorsed by other people. So this happened at Wealthfront for tax-loss harvesting in a couple of - I mean, at least one financial trade press blog that covers all the FinTech happenings. Then it happened at Segment when we launched a product called Sources. The TechCrunch article that came out on the day of the launch, on the day of Source's launch, had my visual with it. It's very gratifying. That's how you know that it's received well.

Alex Kracov: I've been on the other side of that, of trying to put together the press packet and have all my little gifs and images and stuff. Then it's like no, they just go with some Stock image. You're like, what? Come on. I made this nice thing for you. But I totally get their perspective, too. That's a great, great task that I've never thought of before. Yeah, I've tried and failed many a time.

Maya Spivak: You'll never know. You can't ask. That's one thing you can't do, right? It's like you can't ask the journalists to include your assets. You can only just try to be like, "We made these other things. Feel free to use them if they're helpful," and try to incept the idea of using the assets that you've already created.

Alex Kracov: How did you get the press in the first place? Did you have a deliberate strategy to go reach out to journalists and things like that? Do you think it was just buzzy enough that you were able to ride the Zeitgeist, and they were excited to write about it?

Maya Spivak: We had a deliberate strategy. Well, I'm sure Wealthfront, you can always say that it's buzzy and it was interesting. It was frontier. They called us robo-advisors. At the time when I was at Wealthfront, Andy Rachleff didn't like the term robo-advisors at all. Because, again, this was pre-generative AI, pre-robo anything being a good thing. It's like too much RoboCop and not enough ChatGPT, which is 10 years away. But we had a really incredible PR leader, Kate Wauck. You could interview her next and find out all of her secrets, because she stayed at Wealthfront. A true believer for close to 10 years now. She's incredible. She's been with it since the very beginning and is still there just making it shine.

TV Campaigns

Alex Kracov: Very cool. While you're at Wealthfront, I think you ran a big direct response TV commercial campaign. I'd love to spend some time talking about it. Because it was really interesting as I was reading a little bit about it. I'd love to start with the beginning. Why did you decide to run a big TV commercial campaign? What was the strategy and your thinking going into it?

Maya Spivak: Well, we decided to run TV ads partly because it was time. We perceived it to be timed within our growth trajectory to really try to break out into the mainstream. One thing that we were doing really well is appealing to people who had an easier time picking up the idea that software does things better than humans can, and you should automate your investing. Those people happened to primarily be in Silicon Valley and then in New York, of course. Usually, they were engineers, software people, tech people, product people. They're just software adjacent. And so it was not unusual to them to think this way. It was not unusual to them to seek out software solutions to the everyday questions that they were asking themselves about their own investing, their own finances, and their own money. It's early fintech. Robinhood was maybe just on the being born side and certainly not - this was pre-AMC theater is crazy. Everybody is using Robinhood to invest in meme stocks like that. None of that was happening. This was like, can you trust a computer to do any of this? We just barely had passed over peak online banking. Can I get an online bank?

So we needed to go mainstream beyond the people who are already comfortable with it. We wanted to pick up regular consumers. What the regular consumers do at the time, they were just beginning to cord cut. Sure. But plenty of them were still watching TV with commercials. And so we picked up. It wasn't enough for us to do one commercial. Because one commercial, we thought it was just too risky. You don't know what a mainstream consumer is going to respond to. You can commit to a brand idea and one campaign, but it's expensive to do that. It's expensive to go all in. So what we wanted to do was, actually, we created a lot of different ideas. We tested a lot of different creative concepts. So we bought the same amount of time on the air as we would have for one commercial. But we created 35 commercials instead and just plotted them in over the same period of time, which was basically over one year. We did it into half. We created first 15 to 20 commercials. Then we were like, let's do it again. Let's do another 15.

The reason we did that was because we really wanted to see what people reacted to, what got them going, what got them clicking, what they wrote in about. Frankly, it surprised us. Everyone had this internal - we didn't actually do best, but it was as though it was a pool where I certainly thought that you don't need that guy. Commercials would go pretty well. It wasn't that. It was the ones that were a little bit more fear, uncertainty and doubt oriented, where people were moved into action by thinking about their futures and their retirement and running out of money and having to flip burgers in retirement. That was an actual storyline to a commercial that we released, that people responded pretty actively too. It's never the ones that you think it's going to be. So the idea that you would commit, go all in on one script and one storyline. Now that I've experienced in doing the opposite of that, it's a little bit shocking that anybody does that.

Alex Kracov: It must have been just a ton of work to create 35 different commercial spots. Did you just test the messaging in each commercial or their unique actors and setups and scenes? How drastic was the test?

Maya Spivak: Yes, good question. We had to do it in a scrappy way as possible. One way we did that was, we worked really closely with this one production company in LA that I had sourced. They were incredible in that they were really willing to be catering of their work staff to this scrappy approach. What we did was, we booked one location across four days. Over those four days, we would do one scene. Basically, one setup per day, which meant that we started our script making within certain constraints that would enable us to book a set like that.

For example, on day one, we would record a set that was inside of a house, inside of a kitchen. In the kitchen, we had two different scripts, two different scenes, two different setups but with the same actors. Basically, now you have two different commercials recorded in a day within one set. On the next day, you could record in the backyard. Because you would be set up in the backyard and you had a whole different script, and you had the same actors - they were wearing different clothes, but they had a different scenario that they are running through - now they're doing a thing in the backyard. You're still on the same set. So you've extended your stay one day. Then the next setup that you record is on the couch in the living room. It's a whole different scenario that they're running through why they need to do automated investing. But now they're sitting on the couch, and there's two dudes talking to each other. These were our hipster series, which actually did do pretty well.

Then in the afternoon, they're doing the yoga scene which is in a different room in the house. They're both doing yoga, and they're talking about Wealthfront. It was ridiculous, and it was fun. It was funny. But you can see how basically that all aligns into these economies of scale where you envision the scenarios within the constraints of the cost of the set and the production. But once you get that out of the way, those set costs, then you're able to be really creative in your storytelling within those constraints. Oh, we have a house. Great. We have the backyard. We have a living room. We have a couch. We have a kitchen. We have this. We have a fireplace. We have that. What stories do you tell within those constraints? So you can be a little bit more scrappy than you might imagine.

Alex Kracov: Yeah, I filmed one commercial in my life for Lattice, and we didn't have a huge, huge budget. But it was really interesting how the constraints just informed the creativity. Because once it was like, okay, here's my budget, then the agency and the director we were working with was like, "Okay. Well, here's what we can do. It can only be a one-day shoot at one location." Then the script in the story all sort of forms around that constraint. Honestly, at first, you're like, "Oh, that's annoying. I want this. I want that." But then, it actually sort of forces the idea and makes it better along the way. It's really fun to me though.

Maya Spivak: Totally. It's totally fun. I think, honestly, if I had to boil down my most saleable marketing skill that I learned across that year of making commercials, making short films, if you will, if you'll grant them that artistic license is, if you understand the constraints of production, you can do incredible storytelling. And if you have that opportunity once, twice, three times, you can take that skill with you wherever you go to become a marketer thereafter. You understand what goes in here. Suddenly, the people that you hire - the production crew, the contractors, the freelancers - they're like, "Oh, my god. Are you speaking my language?" Because it's so frequently you're not speaking the same language.

You, as a creative person, as a marketer who hasn't done any production, you have visions. But they're based on things that you've seen on the other side of the screen. You've never seen how it gets made, how the sausage gets made. Once you see how the sausage gets made and you start setting up your campaigns and speaking the language of the sausage makers, oh, my gosh, you can achieve so much more economic output. You can achieve better relationships with your vendors. You can work more efficiently. It's incredible. So learn the language of the sausage maker. That's my takeaway there.

Alex Kracov: I love it. We got to clip that one.

Maya Spivak: Yeah, exactly. Learn the language of the sausage maker. That's the intro.

Alex Kracov: Then you mentioned this in the beginning as you're talking about the campaign. How did you actually measure the success? Did you have unique URLs and commercials, or was it more just like qualitative feedback you heard? How did you think figuring out which variation worked?

Maya Spivak: Yeah, we actually tried to be as programmatic as possible, in that we hired this one agency that specialized in commercial awareness, not commercial but literally TV spot awareness and measurement. What we did was, we, again, were pretty scrappy with how we purchased our spots. I don't remember the terminology anymore. There were some very inside baseball terminology. Maybe it's not really a thing anymore as everyone has cut the cord. But when you're buying spots, there's a difference between buying spots on cable versus the different local access, these different channels. So there are certain channels that, broadly speaking, cover the entire United States no matter what cable network you're on. And so the cable companies, whatever contracts they have, enable them to just play the feed.

Then there are some that are broken down by geography and regions. So regional buying, you can do where you know, for example, that your spot is going to be on Bravo and on ESPN and on E! or whatever during this very specific time slot in these very specific regions. So I'm playing like Midwestern on Bravo at 4 PM Central time, and I just know that that's when my spot is going live. That's when I'm going to watch app download traffic, and that's when I'm going to watch traffic to the site in rolling eight-minute increments. The math there was really specific. It was like, okay, for these eight minutes, this was the traffic coming from Chicago or the Midwest area. Then the next eight minutes and the next eight minutes and the next eight minutes, the commercial happened in the following eight minutes. Oh, my God. Spikes, actual real spikes. You can start to measure that. You're not going to have 100% accuracy because that's not how people think or do stuff. But certain commercials just move people more than others. You would actually see spikes from mostly mobile. Because if they're sitting there watching TV, most likely, the traffic is going to be coming from a phone if they're very curious and they were moved into action right there after. That's how we would measure.

Joining Segment

Alex Kracov: Yeah, it makes sense. It reminds me of something I tried to do at Lattice too as we put billboards in different cities and then would watch the uplift in traffic from when we put a billboard. But it was the eight-minute rolling increments that have been really fun and exciting. That sounds awesome. All right. Let's switch gears a little bit. After Wealthfront, you joined Segment. I'd love to know why you did join Segment. What was it like when you joined?

Maya Spivak: The reason I joined Segment is because I was looking to get back into B2B marketing. I think B2B marketing and B2C marketing are pretty, pretty different animals in different specialties that you end up really flexing. The reason I wanted to get back into B2B is because I had been having a really interesting adventure with B2C selling consumers - sophisticated investment services, basically. When the market was up and to the right, which it was for several of those first years, you just felt like a genius. You just pat yourself on the back. Like, oh, my gosh. I'm the world's best marketer. This is the world's best company. Everything's going well. Everything's up and to the right. Then the second the market gets just a little bit choppy, just slightly volatile; you can see that reflected in people's actions. Because they're moved to this degree when they're thinking about their money and their personal assets and whether or not they can afford it. It's like a very true, gripping fence.

As a marketer, I got to this place where I was like, oh, man, there's truly nothing - there's very little I can do to convince people to do the right thing. It was kind of like a little bit demotivating. It was difficult. It was incredibly challenging to be. I know that the right thing to do when the market is volatile is nothing. Don't do anything. Stop opening your app. Don't even look at it. It's not doing you any favors. You're not going to change the trajectory of the market by getting stressed out, upset and worried about it. Certainly, what you don't want to do is sell, sell, sell, sell, which is your first instinct and the thing that most people do. That's literally the opposite of what you should be doing. In fact, the truly sophisticated investors buy more. Because they're buying at a discount, generally speaking, in the world of passive long-term investing. It's very, very difficult to convince mainstream consumer to do the right thing. Because it goes to what they want to do, which is like cut their losses and peace out. So I wanted to get back into B2B marketing. Because my point of view is that a B2B consumer is just a little bit more rational, a little bit more logical, a little bit less motivated by their gut, and a little bit more motivated by education and rationale. Probably, it's not their money, so they're just not quite as worried about it. When I joined Segment, there were 60 people. We were selling a very clear type, a very clear cut B2B product that had no overlap with your personal life, which really quite appealed to me.

Alex Kracov: Now, the hard part with B2C, it's just like so much about the cultural zeitgeist. It gets trendy, and then it doesn't. It's hard to catch those ways. As an entrepreneur, you're always like, oh, you kind of started the consumer side. That's fun to make things like that. But then the best part about B2B is like you're solving a real business problem. Your customers will talk to you, and tell you exactly how you can solve their problems and how you can get paid to solve their problems. And so, yeah, I figured that out when I joined Lattice. I was like, okay, this is a better spot for me to play as well. It seemed like when you first were at Segment, you focused on demand gen. Then you switched back to your core competency around brand and comms. Can you talk about what that experience was like in the early days, and maybe the evolution of the marketing team at Segment?

Maya Spivak: Sure, yeah. When I started, there was another marketer and myself. Then we grew teams around us. Basically, in the earliest days, you're just hired to just help us do marketing, just help. Just come here and help. And so literally, my first project within three weeks of arrival, well before I even arrived, I got an email from the first marketer being like, "We're launching a product within a month of your arrival. Woohoo." She's like, "I know that you love video." Because I had just come fresh off the Wealthfront year of commercials. "Should we do a video for this?"

Despite the fact that I got hired in to be a product marketer, I'm arriving, on day one, hiring the same production company, doing the same setup and immediately flying to LA to shoot a commercial and a series, actually a series of two - to one, say what a Segment, and two, launch Sources, which was the first product. Despite what you're hired in to do or what your title says, at those earliest stages of startup, you end up doing all the things that needs to be done. Then it quickly becomes evident what you're good at, what you really spike in, what the other person spikes in, how you're complementary with each other, and how you're going to grow the teams. And so, yeah, over time, we actually ended up having a discussion, Diana and myself, being like, "I love and it fills my cup to do brand marketing. This is what it means for the creative component." She's like, "It fills my cup to do product marketing." We literally ended up switching. And so that's how we grew.

Then soon thereafter, we had a VP of growth join, Guillaume Cabane. He's definitely known as the mad scientist. I can say with 100% certainty, he's still a mad scientist. I recently hung out with him. He was just like, his crazy spike and the thing that fill his cup, and the way that he got energy was to think up these off-the-wall outlandish growth experiments would make them live quickly. Half of them will work, half of them wouldn't. We would just run all together. I would create the campaigns, and Diana would actually write in this is how the product works within the realm of this campaign and who we're selling it to, and who actually would care about this feature, this component. Guillaume would be like, "Deploy crazy tests that strings together 17 of our martech tools within our stack. Does it work? Do we get more leads in the pipeline? Are the salespeople fed?" That's how we three worked together over time.

Building the Segment Brand

Alex Kracov: I love it. There's such a good lesson in there around, one, focusing on exactly what you want to focus on, and also just being flexible in the early days of a startup. So many things are changing. So many things are moving. You just shift to where you personally both can add the most value and where you're having the most fun. I'd love to go deeper on brand building, because I think it's a really hard activity for people to grok and understand. It's such a nebulous activity. And so how did you think about building the brand at Segment? What does that work actually look like? Are you creating a bunch of internal positioning documents and then going to run and make commercials? Can you take us behind the scenes of that?

Maya Spivak: Yeah, I think in the earliest days, it really helped to get into almost like an establishing shot, an establishing shot in movie lingo. It's that first 30 seconds of a film that you're watching where you're supposed to be able to tell where you are based on what you see. So the establishing shot of Manhattan is classic. Looking down, you see Central Park. You see the tall buildings. Establishing shot of San Francisco is usually, but not always, the Golden Gate Bridge. Despite whatever part of the Bay Area the film is actually shot in, first thing you see is the Golden Gate Bridge. You're like, oh, I'm in the Bay Area. So if you can have an establishing shot for your brand in the very beginning, that really helps. There's some understanding. If I showed you this, you'd be like, "Yeah, this feels right. This feels right." What I mean by that is, I think it took those first set of videos.

First of all, you pick a script, and you do it with your founders. You pitch them a series of ideas. They only like a few. Then you narrow down to what feels right when we talk about Segment, what feels right when we think about, you're going to see this on a screen. It's going to be the first representation of a story that we're telling, that is an analogue to real life that makes sense to you. The styling of it is specific. The words that we use, that's setting a tone. We have to be completely in alignment that we love this, that we're proud of this. If you get that right, you can actually just see. You can just basically see the line that comes out and all of the branching paths that the marketing campaigns of the future take. But you can trace them all back to that establishing shot.

For example, at Segment, our first video was, what is Segment? If you search that, it's still live. My girl with the red hair, she's an engineer. Her name is Cassie. We named her. She's the actor in the video. She is sitting inside of a really rad helmet-making company. I used the word 'rad' specifically because she says, "I work at a rad helmet-making - I make rad helmets. We make rad helmets." A customer can design their own helmets. The whole thing was fun and interesting and quirky. We made a whole bunch. The production company made these ridiculously cool helmets that were just like a motorcycle hipster's dream, which are the spikes in the hair and the polka dots and whatever. We built all of that so that we can put them all in the establishing shot for the video. She says the word rad a couple of times. We explained what Segment does. She's still a software engineer. She's still in her element. She's still taking time to explain somewhat realistically the concept of what Segment is. But we've set the establishing shot.

The reason the video is still live six years later, seven years later, is because it turned out to be evergreen. You don't always go into brand building with the idea that your work is going to be evergreen. But if it worked, it worked. It's like this magical moment where all the stars have aligned. And so I think if you can get an establishing shot that you are very proud of within the company, all of the most important stakeholders, the founders, or people who are building it from the ground up, they feel proud of that work, you're just going to see it. You're going to keep building off of that, as opposed to they're not proud of it. You actually see it changing quite often, which means there's no consistency, which means there's very little recall. That's when you're not doing a great job building that brand.

Alex Kracov: And so you have this establishing shot that sets the tone for the brand. But then, the product and everything evolves. The market is evolving. Your competition is evolving. You're adding a bunch of new products into the suite. How did you think about evolving Segment's brand over time, maybe what would it look like five, six years later?

Maya Spivak: Well, to some extent, it really becomes higher and higher production value. To some extent, you also just expand to the places where you are building a brand. The style of our video production didn't really change. What we did do is add in a whole bunch of different channels over five and a half years that I was there, where we were establishing our brand. In the beginning, it was just with some videos. Then it was, we put on a user conference. The first year, it had its own brand. It was called Synapse. The first year, there were 400 people. The second year, there was 800 people. The third year, there was closer to 2,000 people. You were building the Synapse brand in parallel with Segment. Then you do billboards each out of home. Even your billboards change in style. Then maybe the culmination is like a three-dimensional physical board with props on it. That's in the Bay Area. If anybody listening is in the Bay Area, off the 80 East going towards Bay Bridge, it's still up.

Alex Kracov: It's a great billboard. I know that one well.

Maya Spivak: Yes, thank you. It makes me really proud every time I drive past it.

Alex Kracov: Let's talk about the user conference, then we'll go back to billboards in a second.

Maya Spivak: Sure.

Hosting a User Conference

Alex Kracov: So Synapse, you talked a little about the evolution in terms of numbers. But why did you even create a user conference in the first place? I mean, I know. When I tried to do this at Lattice, it was so expensive. A lot of work, right?

Maya Spivak: It's a lot of work.

Alex Kracov: Why did you do it? Can you talk about bringing it to life?

Maya Spivak: It is a lot of work. You really, as a startup, have to think really hard about when you're ready for it. Because basically, I do think that once you debut a user conference, you can't go back. You're not going to stop doing it, and you shouldn't stop doing it because that sends a whole different message. "It didn't work. We failed at this. We don't have enough users per user conference. We can't justify this." You don't want to do that. You don't want to be that startup. So if you're committing to a program, basically, for life, you have to make sure you're ready.

So why do you do it? Because all of the best tech companies have one. Because you have a community of users out in the world, somewhere in the wild, and bringing them together where they're all in the same place at the same time learning about your product. Because they're actually kind of excited to be there and learn about what you're debuting, there is no better gratification for a software company than actually seeing it. You spend every single day building stuff for people. You're delighted when they use it. You're delighted when they buy it. But there's nothing that feels better than when you get them all on the same auditorium, and they're rip-roaring ready to hear you say what you're about to announce as a product. People clap, applaud, and whoop and cheer, and you didn't pay them to do it. It's a rush like you've never experienced before.

On the business side, you're looking at retention. You are looking at contract expansion. Because typically, you're trying to align your conference around - you're launching something big and new. You want to launch something big and new every year if you can. Every time you do, you do it on the hopes that it will make your product more sticky, or you're going to charge more for it so it will make your company more money. You have literally a focal point to align the entire company around. We're launching this in March or nothing. There's no other choice because we put it up. We sold the tickets, and we're going to be there in March. We're going to launch this, which is where, in some cases, you see a vaporware launch. It's because the cart got put before the horse. You didn't actually build the product. It's not ready, but you have the auditorium full of people, and they're waiting. So it's got to be launched somehow. But unfortunately, that is also a type of standard that you can fall back on if you really need to.

Alex Kracov: Yeah, when we did this at Lattice, it was amazing to watch the crazy amount of internal focus and push towards the conference, but then also just how excited everyone was when the conference came. The look on Jack, the CEO's face, when he got on stage. You could feel the community and stuff that he had helped built. Just everyone was smiling and exciting. I don't know how much revenue or pipeline or whatever it drove, but it definitely retained employees. It got customers so excited. We sit behind our computers all day. It's so different to be in a room full of your customers, and everyone is super excited. It's an amazing feeling.

Maya Spivak: Totally. I 100% agree. But then, you have to keep doing it every year.

Alex Kracov: Yeah, do you have a recommendation for companies thinking about this? Is the best way to think about it budget perspective? I think at Lattice - I'm trying to remember the exact numbers - we did a smaller one for a couple 100k to 400 maybe. Then it was like, oh, let's do a million dollar one. COVID hurt that idea. But I don't know. How do you think about when should companies do this?

Maya Spivak: Well, as far as when, I actually think that it's okay to start small. You don't have to wait until you have thousands of users or thousands of customers. It's really about when you want to start punching above your weight class, but you're ready to commit. You are dedicated to the idea of forming and feeding a community around your product. If you can envision one future day where Dreamforce is like one of your guiding stars, you can envision doing a conference for 20 years, and the audience just gets bigger and bigger and bigger, it's time. That's when it's time. It's when you can actually envision it. You can actually tie a thread even if it's a dream thread. That's when you can start, especially when you're on a project roadmap or product roadmap and want cadence where you can actually start sorting away from just constant small launches into let's have a big vision. Let's share a big vision. Let's unite customers around a big vision. That's when it's a good time. You can start small. By small, I mean 100 people at conference. It's still great. It's still a great time, because you record the whole thing. You have the video for video on demand afterwards. You could stream it. People can stream it as often as they want. 100 people inside of the correctly-sized space are still having a really great time together when it's a well-produced, high production value unit.

I always used to think about it. I know this is probably not the gold standard of an event planner. But I used to think about it on a cost per - I would think about all my stuff has a cost per unit. That, for me, was the simplest way of keeping track and not letting things go too far awry. For me, a golden number was about $1,000 a head. $1,000 a head per Segment, per user conference and not above that. That's where I kept the line. If you can go all in with your vendors and your services and all the fees and everything stacked up, you spent $1,000 making sure that one customer in the audience has had a good time that day, you don't need to go too far. It's really easy to spiral out of control and then spending a lot more than that. But you don't need to. That's about the amount where you can keep them nicely fed, they had a good time, and they were accounted for eight hours that day. It felt like pretty high-production value.

But on the flip side, it's scrappy when you actually start to break it down. In fact, with service costs being really really, really high now in a city like San Francisco where there's a lot of unions and labor unions inside of large enough spaces, now maybe it's like $1,200, $1,300. But you do not need to be spending $3,000 per head. Then another mistake that you don't need to make is you think about your conferences, the time that you're going to get the whole company together and attending your conference. So this is when you see. I see that you've been there. You are seeing 50 customers in the crowd and 100 people from your staff. Now what did you just do? You spent $1,000 per head. Because it's just like $1,000 per human person who takes a space. You're blowing it on the people that already worked for you, as opposed to the customer. So we would only let people come physically to the conference if they had us on the stage, if they had some form of work to do in terms of boosting or selling on the floor, or volunteering, directing people to the bathrooms and whatever, all that kind of stuff. Otherwise, you're sitting at the office life doing it from there.

What Good is Bad Data Campaign

Alex Kracov: Yeah, you made me think of some very funny internal conversations where it's like, "You guys can come. You can't." It gets dicey. But to your point, it gets so expensive. Yeah, I think we actually had a very similar budget, $1,000 a head. But that's where it's like, oh, a million-dollar conference? It sounds crazy." But if you want 1,000 people at a conference for $1,000 per person, there's your number right there. It's really hard to do that. In 2019, you ran a national campaign around a great slogan: what good is bad data? Can you talk about that campaign, and why did you go with that positioning? What were all the different elements of it?

Maya Spivak: Yeah, sure. What good is bad data? I think the answer, it should be simple once you think about it. What good is bad data? It's no good. It's worth literally zero. If your data is wrong, you got nothing. That was Segment's whole product. If you tie that up in a nutshell, how easy is it to get your data wrong? If you don't have a central repository for it, and you're sending different conventionally structured data to all these different providers that you have, and you probably have a lot of providers, the chances of something going wrong are very high, unless you have really great data at the source. The source is what sends the same set of data to all the fans out, like inspiration vendors that you have. We needed a pithy way to tie that up. So that's what good is bad data. But what good is bad data is just like the overlapping idea. That's the closest analogy to a one-liner that you could say. Yeah, so that's what Segment does. If you think about what good is bad data, no good. Yeah, that's what Segment does. Make sure your data is good, so it's not worthless. But then, you need offshoots of that campaign slogan, basically, to make it work, to make it obvious, to make it click for people.

And so the first offshoot that we came up with that made it click for people, we did it sitting in a room. Because our billboard, our placement had to go live within a month. We had nothing and we didn't have a creative agency. We had a brain trust sitting in a room together, the most creative people of the founders and some of the leaders in charge of selling, just being like, "What are we going to put? What are we going to put?" The head of comms who worked on my team, he was so brilliant. He says, "What good is bad data? What if the billboard just there like Good Morning, LA?" The first spot, we're in San Francisco. The first spot we're talking about that we bought is a board in the city. Everyone's like - we just all burst into laughter. It seems so ridiculous. It seems so outlandish to put a board up that does Good Morning, LA in SF. That's when we knew it was, that it's still ridiculous. We have to do it. But it wouldn't have worked unless our establishing shot that we had from the beginning was like, it's okay to be quirky. It's like, we're going to lean into the quirk. We're not going to be weird about it. But it's always going to be slightly quirky. And so that was okay with everybody in the room, because it had been a part of our culture for years. We launched with it, and it went viral. Because we played it also. We put, "Good morning, LA," all over San Francisco. In L.A., we had, "Good morning S.F." in a whole bunch of places in LA.

First of all, the people that immediately got it, you knew who they were. They were data people. They were tech people. The kind of feedback that we got on Twitter and anecdotally and just people sharing and writing us emails about it was like, "Hahaha, you made me laugh on my bus ride this morning." Then we got this other class of feedback which was actually like a GIF. It was a GIF in disguise, which was, people were ragging on us because they thought we made a mistake. They thought we spent hundreds of thousands of dollars making a mistake as rudimentary as putting the wrong billboard in the wrong city. They're like, "Oh, I think you guys made a mistake here." Or, "Did you mean to put this there?" There were just so many people who shared about that out into social media just anxious to be like, "Oh, I found a mistake out in the wild." But that was an unexpected source of virality. So that campaign worked really, really well in two different ways.

Alex Kracov: I still remember that campaign. I remember driving around SF and seeing it. I know that billboard. It makes you go aha. It's just that was so memorable and funny. That's the secret to good billboard advertising. You can't just have your vanilla messaging out there. It's like, Segment is a data platform. It's like, no, if you need something that gets people to laugh a little while they're driving their cars, distract them and stuff. So yeah, it's awesome.

Maya Spivak: Yeah, you do the best you can. There's no formula. It's just like, every so often, you get so lucky. You work with creative people. Everyone laughed. You're like, we're writing it. We'll do it live. We're going to try it. Stroke of luck.

Alex Kracov: My best campaign was in the first crypto craze. We were selling HR tech company. We put up a billboard. Invest in your people. Not crypto.

Maya Spivak: I like it.

Alex Kracov: We got a ton of angry crypto people yelling at us and stuff. But then, it was a good message that we wanted to send that stood out. It was funny. Coinbase wasn't too happy. But it was good.

Maya Spivak: That's funny. Well, I bet you had both types of people. You had the angry crypto people being, "What the hell?" Then you had people on the flip side of the crypto bros, like very anti-crypto bro being like, "Thank you. Yes." You know what I mean?

Alex Kracov: Yes, exactly.

Maya Spivak: You actually have these opposites. Maybe there's something there, which is you look for a way that you can speak to two groups of people. And you wouldn't mind speaking to two groups of people.

Alex Kracov: Yeah, well, that's the hard part with billboards in general. It's like you're speaking to everyone. Everyone is going to see this. And so you need a way to cut through the noise to your audience but also somehow talking to other people too. It's such a tricky little balance there. But it's fun. Billboards are really fun.

Maya Spivak: I agree.

Alex Kracov: I spent so many times walking by people with desks of being like, "What do you think of this ad? What do you think of that ad?" It's fun to come up and scary, too, because you're putting this big message out into the world. You can't really change, if not in the digital.

Maya Spivak: Yeah, totally. I mean, you have like a month, right? Within a month, you can scrap it. But you don't want to. Because then, you're giving into no recall.

Segment's Acquisition by Twilio

Alex Kracov: Yeah, exactly. So Segment was eventually acquired by Twilio. You were there for that acquisition. I'd love to just hear what that was like from your perspective. How did that impact your job as running brand and comms? Did you have to update all the positioning? Was it more independent? How do you think about it?

Maya Spivak: Yes, actually, there was a moment in time where it was immediate, you are immediately thrown into the fire. You have to integrate their messaging as fast as possible, because you are being absorbed into a publicly-traded company. And so there's a lot of things about the way that publicly-traded companies are regulated in the way their communications are received and the way that communications are put out into the world. Basically, you're not messing around anymore because they're regulated. They're your mom now, and so you have to do stuff that mom says. Within a week, you're on calls about some brand's directions for the logo. Is it going to be put Segment by Twilio, Twilio-Segment? Is it going to be Segment or Twilio company? There's optionality there. And so you try to look at other examples of the way other software brands that were acquired into the Twilio family. What did they do? Should we be consistent? Should they not? Of course, you're going with the flow of what your new corporate overlords want. That's fine. Again, they're your parents now. And so you go with it. That's how Segment became, Twilio-Segment. That's how the logo, I think, in the last year became capitalized again. It's just like these brand decisions that you have a different mom now.

Maya's Brand & Communications Advice

Alex Kracov: I love the parents analogy. It's a good one. So I'd love to end today's conversation by just maybe giving some advice to startups or founders who want to start investing into some of the things that we've talked about today, brand and comms. What advice do you give them? When can they start investing in these activities? When do you maybe hire a dedicated team? As you're talking to other founders or marketing leaders in this world, what's your advice for them?

Maya Spivak: That's an interesting one to try to just boil down into some advice tidbits. I think creativity is the thing that you are looking for when you are trying to build and engineer churn your own brand. The best thing to do is look around inside of your company and understand and find where the creativity is. Because, believe it or not, the type of creativity that I'm talking about is not everybody's skillset. That's literally the reason agencies exist, creative agencies. You know Mad Men, the Don Drapers of the world? It's a skillset that is unique to certain people. They gravitate towards the creatives of the world. You can turn around and say they don't have plenty of other skills that you probably do as a founder or a technical person or whatever.

The way that I am creative and the way that I spike in the work that I do, I have matching deeds on the opposite side. Where, man, being analytical about something or filing out a spreadsheet, that's the kind of stuff that would scramble my brain. It'll start oozing out from my ears. So these opposites, recognize that it's a skillset. Then find the people in your company that have this. They are not always distinctly working on marketing. That's okay. Pull them into a room for a few seconds on closing the creative component parts of your brand and be like, "How do you talk about it when you talk about it to your friends and your family and your partners and your significant others and your creative people in your life, and your side hustle gang? How do you talk about it? What's the latest campaigns that you have seen out in the world that you thought were cool?"

Get the download from the people that are closest to your company that are actually creative. If there's literally zero people, you can start looking outside of that. You can bring in a creative. The agencies, they exist for you. But don't just don't that you actually might have a creative people internally that aren't specifically cost-wise as marketers. But they will, they are the people that will come up with like, "Wouldn't it be cool if we did this thing at this competitor event if we put a billboard that looks like this?" You're like, oh, my God. That is the coolest idea that I've heard in a long time. I know you're not a marketer. But I trust that you're creative, and you love this brand. Or you love this company, you love this product. Let's do this thing. That's where I would start. Look internally. If you don't get it, you go outside. Okay. Find those people that you bring in to your hold. Then you start there.

Alex Kracov: Love it. Well, thank you so much for a wonderful conversation, Maya. If people want to reach out to you and learn more - I know you're maybe doing some consulting these days to help other startups and founders - where can people find you?

Maya Spivak: Yes, I think the easiest way is find me on LinkedIn. I am Maya Spivak. Find me on LinkedIn. Shoot me a note. Connect with me. I'm always happy to connect. Plus, I'm in San Francisco. So any chance to meet IRL after these three years of being shut in, I'd take those chances. So yeah, hit me up. LinkedIn is probably the easiest way.

Alex Kracov: Awesome. Thank you so much.