Growing Upmarket | Lauren Weinberg

Katie Foote: Welcome to Revenue Talks. I'm Katie.

Justin: And I'm Justin. And on this show, we get real about what it takes to build pipeline and successfully scale businesses.

Katie Foote: By having conversations with folks who have been there before, we explore what it takes to create strong, cross- functional alignment, how technology factors in, how different teams think about attribution and so much more.

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Katie Foote: Hello everyone, and welcome to another episode of Revenue Talks. My name is Katie Foote and I am the CMO here at Drift, and today I am so excited to be joined by Lauren Weinberg from Square on our show. So Lauren has been the global head of marketing and communications at Square for four years, and as a part of this role, she directs the channel and creative strategy across all of Square's marketing channels, including search online, display, organic social, content, email, television, audio, you name it, she does it, and we are so excited to have her. Lauren, welcome to the show.

Lauren Weinberg: Thank you, Katie. Thank you so much for having me today.

Katie Foote: Now over the past four years, Lauren, you have worked and been heavily involved in scaling Square's brand upmarket, so we're going to spend a lot of our conversation and time today focused on how you've done that and how the business has changed over the past four years. But before we get too far into the weeds on that topic, I want to give our listeners a little more context about you and your work at Square. So you joined back in 2017, which feels like a lifetime ago, pre- pandemic, and you started as the global growth strategy lead and are now the global head of marketing and communications. Can you talk a little bit about that four year journey and what it first looked like when you joined Square to where you are today?

Lauren Weinberg: Absolutely. So I couldn't agree more that the four years ago does feel like an eternity ago, and I'll just back up a little bit and say that before I even joined Square, I've been in marketing for my entire career, so more than 20 years, and right before I went to Square I actually was running my own business. It was a strategic advisory firm, marketing with both startups and larger businesses to help them with their marketing strategies, and when I joined Square, it was really amazing because I just wish I had known about all of the solutions and tools that I could have used as a business owner when I was running my own business. But when it came into Square, I think the first thing for me was just realizing that Square had so many products and solutions that I had not heard of yet. So a lot of what we've been focused on is really growing awareness of all of those things and the way that those things really work together. We've been through a time of just tremendous growth in scale over the last four years, and over the last two years in particular, so in addition to growing upmarket, we also are expanding internationally. So we just launched in Spain yesterday.

Katie Foote: Congratulations

Lauren Weinberg: Thank you. And we launched in France and Ireland in 2021. So lots of global expansion and just lots of growth and scale, and I would say probably the other really big thing to call out is that when I first took over marketing, the team was actually called the channel marketing team. And that is the way that the team really operated, which was very much around the channels and everything was about channel specific strategy. And a big change for us is really, A, we're not called that anymore, we're just the marketing team. And now we really think about holistic strategies and all the channels that you need to use. And as you're growing your brand upmarket, there's lots of different channels that you need to put into place, but really it's a much more integrated, full funnel approach that we're thinking about in terms of how do we leverage all of these different pieces together, connect all the dots to really communicate to our audiences,

Katie Foote: And audiences have such high expectations. If we think about our own preferences as consumers, we want right message, right time, right place. So having that integrated strategy I think is really key to breaking through the noise and into the market today.

Lauren Weinberg: Absolutely.

Katie Foote: Well, very exciting. One of the big focuses at Square, as you and I have talked, been around expanding and going upmarket, you mentioned some of the changes you made early on of focusing, moving from channel to marketing in general and creating that holistic journey. But what other steps did you take on that journey to expanding upmarket?

Lauren Weinberg: Yeah, so I think the first one, and this is not just true for expanding upmarket, but just to go to market in general, is making sure that you have the right product market fit. So I think for us, that was probably number one. And when Square started in 2009, we really started to enable individuals and businesses of any size to really participate and thrive in the economy. Well, now it's 12 years later and we have this entire ecosystem of solutions, of commerce solutions, software and hardware that really enabled businesses that have much higher complexity to be able to operate and run using Square's systems. So I think number one was just the evolution of all of our products and services to meet the needs of more complex operations. So for example, we're now in SoFi Stadium. We also work with Powder, which is the largest ski resort operator in north America. So number one, just having the right product market fit to meet the needs of those businesses. And then I would say the second thing is we do a lot of research and we really talk to a lot of customers to really fine tune and hone our go to market strategy. So in the early days we would talk to a lot of these larger businesses and we would hear them say," I love Square. I just don't think it's a business for me." So that was one of the things that we really work on in terms of our go to market strategy for larger businesses is helping them understand and see that we do have the tools for them. So we listened a lot to what were their perceptions of us as a brand, and then also understanding what are the needs and challenges that they have, who are the kinds of people that we'll be speaking to there. And we have a lot of different opportunities at Square to shadow calls with sales teams or shadow calls with our account managers or shadow calls with our customer success advocates so that we can actually hear for ourselves what are the things that these businesses are asking about? What are the kinds of questions, and all of those insights really help us fine tune our messaging.

Katie Foote: That's great. It sounds like... You referenced this already, but you did a lot of research. As you expand upmarket, that often means going outside of your traditional ICP, ideal customer profile. Were you spending some time researching other personas that might not have been your existing customers, and what was that process like?

Lauren Weinberg: Yeah, absolutely. So I think prior to a push to really grow upmarket, most of our target audiences was the owner of the business. Now as you are thinking about a more complex operation, there's actually a lot more stakeholders involved in the process. So maybe it's their chief revenue officer or their chief technology officer or information officer. So for us, a lot of it was learning who are the decision makers in that process if you're going beyond just the owner or founder of that business, and what are the things that they care about most and how do we make sure that we are speaking to them? And I think sometimes it's a different way in depending on which way you go. So for us, it really came down to thinking about each of those personas, what do they care about most... I always tell people when I'm talking to them the WIIFM, the what's in it for me. So if you put yourself in the other person's shoes, what's in it for them, how are our products and solutions going to make them more successful at what they're doing? So there was a lot of research that went into that, into really identifying who are those new ideal customer profiles? What do they care about? And then how are we going to communicate with them? And then where are we going to communicate with them? And I think that was the other really big pivot for us was the channels and the tactics and the things that we use to communicate with this audience.

Katie Foote: How have you seen those tactics and those channels change over time, especially from 2017 to where we sit today in this pandemic era that we're in, with everything being so much more digital, but as a result, the marketplace being so much noisier than it used to be. What's that evolution been like for you at Square?

Lauren Weinberg: Yeah, so at Square, I would say when I got to Square, it was very much about performance marketing and everything was digital. Over time, and I alluded to this in the beginning, there's so many things that we offer that people didn't know about. So one of our objectives as an organization is just creating awareness around those solutions. And when we set out to create more awareness around all that we have to offer, we definitely dipped into traditional media channels, TV. We do still use a lot of digital TV, so connected TV. We've leveraged print, out of home. We really have experimented with a lot of platforms, including podcasts, radio, just really trying to be in all the places that we know that our audience is. So lots of experimenting with channels. And when it comes to this upmarket audience, I would say the thing that we really are striving for is establishing credibility. So this is where testimonials, case studies really become very critical, and just for the businesses that we're targeting to be able to see themselves in the businesses that we're showcasing in our marketing materials. And we lean very heavily on comms for this because we know that what we're putting out into the world from a comms perspective is going to come back validated by a third party media outlet, and that also gives a lot of credibility to what we're doing. So we've definitely leaned into that area a lot more as we think about this going upmarket. And then I would say we are getting into account based marketing, where we are able to really showcase those testimonials and those case studies and do things that are a little bit more niche and targeted. That's another area for us as well.

Katie Foote: I think customer marketing and advocacy work is one of the most underrated contributors to overall marketing success. When your customers evangelize your story and celebrate their own successes, it just comes with such credibility. I'm also struck by the... It sounds like you've been very intentional with your sequencing. You did the research to understand the key audiences, you built robust integrated strategies, and you can continue to evolve beyond that as new tactics like ABM become available. Now that you've done all of this research and put these very thoughtful plans together, I think one of the mistakes we can often make as marketers is if sales isn't enabled on how to also evangelize your message, it can fall on deaf ears and all of that work could be for not. So how have you been able to partner with your sellers to make sure that everyone is on the same page and putting all of the wood behind the same arrow as it relates to your strategy?

Lauren Weinberg: Yeah, so that's a great question, and I would say we're very fortunate at Square because sales and marketing work so closely together every step of the way. I actually think that our sales people are some of the best early groups that we always test our messaging against because they're on the front lines talking to our customers every single day. So a lot of times there's a lot of back and forth between our two teams around value proposition, messaging strategies, when marketing sits in and listens to sales calls, and then we go back and say," What about this? How will this land?" And then there's just this continuous feedback loop from sales around what's working, what's not working. And a lot of times part of the insight doesn't just come from the research, but actually from the insight from our sales team saying," This is really resonating with people today. This is what's top of mind for these merchants right now. Here's what they want to hear about." And we use all of that to really bring it into our, go to market messaging.

Katie Foote: That's great. I want to go back to something, a comment you made earlier about awareness, and I feel like Square has incredible brand equity and it's certainly grown. Just as a consumer I feel much more aware of the brand than I even did two years ago. How have you been able to measure the effectiveness of your awareness efforts, because that's always a challenge for marketers is there's often correlation, but having that linear tie to ROI with awareness has been a challenge over the years for marketers.

Lauren Weinberg: Yes, and it still is a challenge. But what we've done is we've developed a framework essentially. So we have a couple of short term indicators. So we say once we start really turning on awareness, do we see that there's more search query volume for our brand terms? Do we see more people coming to our site? And do we see more people filling out lead forms? So we use a bunch of short term indicators. We use brand tracking. We have an amazing data science and marketing analytics team at Square. So we're constantly conducting experiments to help us understand how all of these pieces really play together. So we also employ a medium mix model, which helps us understand the incrementality of our different marketing tactics and how our awareness is going to influence overall revenue for the business. So we essentially triangulate across a lot of different measurements so that we have short term indicators, long term indicators, and obviously our overall KPIs as a business. But I would be lying if I said we had cracked this nut and perfectly figured it out. So we continue to really focus, and I would say that's probably one of the things that we focus on a ton as an overall organization, is just continuing to evolve our measurement, find new ways to show the relationship between different strategies, and tactics and continue to find new ways to measure our awareness.

Katie Foote: Well, you've been in marketing for more than 20 years. I think one of the beauties of marketing is yes, the science is critically important and we have grown leaps and bounds in what we're able to measure and what we're able to tie to return, but there's also this intangible art to marketing. So it's the pairing of art and science that I think can really move people through the buying process.

Lauren Weinberg: I couldn't agree more. My background's actually in research and analytics and I think it always surprises people when I say that, yes, you need to take the insights and the research and the data and the numbers, but you also to use your instincts and what you know about marketing, just from your practice of being a marketer or from creative, and really combine all of those things. And oftentimes you need to take somewhat of a leap of faith when you want to try something new, because it's very hard to have data on things that you've never done before. So it's a hundred percent a blend of art and science, and I think it's a constant balancing act of really striking the right balance between those two things.

Katie Foote: And I think as B2B marketers, we sometimes forget, yes, we're selling into other businesses, but they're human beings too. The B2C motion has done such a wonderful job of pulling on emotional heartstrings in some of its marketing, and I think there's a place for that in B2B marketing as well.

Lauren Weinberg: Well, I mean, for us, we definitely see that. I think running a business in particular is one of the most personal things that you can do. And for a while a lot of our marketing actually mirrored consumer marketing because a lot of our businesses were small, so we really leveraged a lot of consumer marketing tactics. So as we talk about this shift and growing upmarket, that's where we start to employ more traditional B2B tactics. So where we're showing up and trade shows, producing case studies. Last year we experimented with some print ads and took out ads in the Wall Street Journal, in the New York Times. And this is where we start really doing more of those traditional B2B tactics. But we always try to really use that emotion just because we know how emotional it is. People pour their heart and soul into running their business, so we always want to connect with them on that level while hopefully also helping them understand that we have a lot of solutions and tools that can really help them thrive.

Katie Foote: Well speaking of your customer base, as you've gone even farther upmarket and really expanded your host of solutions, how have you walked that delicate line of not forgetting where you came from and that core customer base, but also continuing to speak to the new personas you've identified with your new offerings? How have you been able to figure out that balance as you've grown?

Lauren Weinberg: That's also a great question, and I would say one thing that we always say at Square is we're growing upmarket, not moving upmarket, and that's a really important distinction because it means that we are not ever going to leave our base behind. It's really an and and not an or. So we always kind of are thinking about it with that framework in place. And then I would say a lot of our businesses have actually grown with us. So sometimes there's these smaller sellers. For example, Blue Bottle has been with Square since the very beginning of our existence and they've obviously expanded a lot. So we go after a larger businesses, we have the solutions to meet their needs, but we also have free tiers because a lot of businesses start out and then they grow with us. So we want to be able to have something for everybody. So we have tools and solutions that can meet your needs from a very small sole proprietor to a very complex operation like SoFi Stadium, and I think for us, it's really about just communicating the different things for each of those stages. And then the other thing is that all of our research... So we're looking at customer satisfaction, NPS, scores and our branch checker. All of that data is then cut by those segments, so we're able to see how satisfied our customers and each of those different revenue segments. Do we see anything starting to slip through the cracks in terms of our core audience and just always being mindful of keeping an eye on how all of our customers are feeling, and we still do a ton of marketing to our base of customers.

Katie Foote: You have an incredible customer list, and I would think a lot of the stories, especially the one about Blue Bottle, is also inspirational to future customers. There just seems to be such energy in what you've been able to build, which as a marketer I'm envious of. you have such a great story to share.

Lauren Weinberg: We do, and I would say storytelling is definitely just a core part of what we do as a marketing organization, and that predates my time at Square. So coming into Square, I think it's something that the company has always done really well. Another one of our operating principles is really around show and don't tell. So that's been around way before my time at Square. And what this means for us is that we love to leverage our customers, their stories, and their voices to share how they're using our products and solutions. It's so much more meaningful than when it comes from us directly. And we do have a lot of just... I mean, we have tons of amazing customers and we have a lot of customers that have a lot of affinity and love for Square, so we are very fortunate in that we have such a great customer base that is willing to share their stories. But it's also a nice opportunity for them, because they're really proud of what they've built and then we're just giving them a little bit of a bigger stage for them to really share their story. So I like to think of it as a win- win, but you're right, that we are so fortunate and we have the most amazing customers who are just the most passionate, resilient group of business owners that you could ever imagine, so we have a lot of amazing content to pick from.

Katie Foote: Well, and that would be so inspirational if you're giving that platform. A lot of times if you're starting a business, I would imagine you need to see it to believe it and say," Oh, I want to be like that." And by creating a space for your customers to share that story, it's kind of a pay it forward cyclical process.

Lauren Weinberg: A hundred percent. And I think that's also very true for these upmarket sellers that we want to attract into our platform. They want to be able to see themselves in the stories that we share. That's why we're always trying to think about a wide range of verticals and highlighting different industries so that at least there's the component that really resonates with our target audience. Oh, I can see myself in that kind of business, or I aspire to be like that business. So that's definitely a part of our strategy as well is just making sure that we have a really diverse mix of the people, the backgrounds, and also the businesses, the location, so that there's something for everyone.

Katie Foote: That's great. Now this whole intentionality around growing upmarket, I'm sure it hasn't been entirely seamless. Have there been any major hiccups along the way or lessons learned on that journey?

Lauren Weinberg: There's always so many lessons learned, I would say. But yes, I think for us, there's been tons of hiccups along the way. We're really just figuring out, I would say... One of the things about us is we have really relied traditionally on organic lead generation. So we just recently started to dip our toe into paid lead gen, and we're learning a lot about which channels work, how much money should we pay, how do we make sure we're passing qualified leads to our sales team? And we have a very, I would say... Our culture's just really amazing, so we're very lucky at Square, but we definitely embrace this notion of seeking divergent perspectives. So we do not always agree about the best way to do it, and we often talk about what we did and I've never seen a company culture celebrate learning from your just... I don't want to say failures, because always to say like we fail forward. We never do something that we don't learn from. But sometimes we do things and they don't work as well as we thought that they did, but they would, but then they give us great learnings for going forward, and that notion is celebrated a lot at Square. So yes, we test and learn all the time. We're always trying new things. We try to do it in a really responsible way. So we're taking calculated risks, not crazy irresponsible risks. But we try new things. We try different market tests. We try different channels to see which will resonate best with our customers. So I would say it's kind of just like a constant test and learn experimentation engine happening on the marketing team at Square.

Katie Foote: That the whole concept of better, better, never best, there's always room for improvement. And I think such innovation can come too from when you create a psychologically safe environment where people can fail quickly, so many cool ideas and learnings can come on the other side of that. And it just feels like constant innovation.

Lauren Weinberg: Agree. And I think it's something that we work to really nourish that. It's not always there. I think it still can feel really scary, especially when new people come into the organization, this idea of we tried this and it didn't work. So I would say just as a leader, I try to do that all the time. Hey, we tried this and it didn't work, and here's what we learned. And I see everybody on the senior leadership team at Square saying," That's great. That's a really great learning." So we try to model that behavior inside the company and then we've hired a ton of people. So I think the hardest part is in this remote work world where people don't get the benefit of being in the same room as everybody, continuing to create that psychological safety and setting the stage for the fact that we do want people to be innovative. We want them to try new things. And sometimes they work and sometimes they don't and when they don't, we learn a lot, and that's great.

Katie Foote: Speaking of being in a very digital first world, how are you creating that sense of community and that psychological safety within your organization?

Lauren Weinberg: I would say it's a constant work in progress. I find it has been surprisingly easy to feel really connected to people that I haven't met before, but I also am really looking forward to hopefully seeing people in person this year. So we've tried a number of different things across our team. We have this concept of coffee talks that we do now, so we are pairing people, so different mentors and mentees and people volunteer like," Hey, I want to learn more about attribution models," and somebody will say," I'm willing to teach somebody about attribution models." Or," I want to get better speaking skills or learn about executive presence." So we have volunteers who say here's things that I can coach somebody on, and then we have a group of people that will volunteer and say I want to... We basically match everybody up. So every quarter, anyone that participates in the program gets to have this coffee talk once a month with their mentor on a specific topic. So we try to do a lot of those kinds of things because that enables people that maybe aren't in meetings together, that don't get to see each other regularly... We do a lot of all hands. We always try to incorporate something fun into our all hands. So we play trivia. We, I think, have a pretty good dialogue going in our Slack channel. So just keeping people connected and trying to always share interesting work or talk about interesting topics. And I would say so far we've been really lucky, we see a lot of engagement, but I think it's a constant struggle of just people are fatigued from being on camera all the time, but also craving connections.

Katie Foote: I know in our personal lives we've learned to be... Texting is so ubiquitous, being on our devices is so ubiquitous. So I think we're able to connect in that world because it's part of our daily lives. I always tell my team, it's incredible we can accomplish even being remote with all of these headwinds, so imagine when we can occasionally touch base what that will do for our team, our productivity, and our businesses.

Lauren Weinberg: Yep. I agree.

Katie Foote: Gives us something to look forward to. What is your team focused on? What are some of the key priorities for you in this new year?

Lauren Weinberg: So measurement's always a key priority for us. I think as we dip into these new tactics and strategies, we want to tie all the pieces together. I think just in general, and you know this too from where you sit, but just the entire industry keeps evolving and changing and shifting. So even if you think you've figured out measurement, something changes in the industry, and you need to revamp it. So that's always a top priority for us, just continuing to innovate there and find new ways to measure and learn. And I think the other thing for us is figuring out... I would say Square has a really great customer acquisition flywheel for how we acquire smaller businesses. So a big focus for us going into this year is really how do we get that same sheen going, the same velocity for these upmarket merchants as well? So the fact that we have never really had paid lead gen until this year is kind of remarkable. So we have a lot to learn there. So I think just figuring out how do we get that kind of up and running and learn a lot about how to do that really effectively? What's the right balance between our awareness and our performance efforts? I think these are all the things that all marketers are thinking about, but for us it would be... Number one is the measurement piece and number two is really how do we get that lead generating machine up and running for Square.

Katie Foote: And breaking through that noise in a very noisy marketplace in a digital first world. And when you mention measurement, I'm always struck by the old adage of what you can measure you can manage. And it's not just, at least from my perspective, a read out on the data. It's what is the data? What are the measurements telling us? What do we need to learn from them? That's where I think the real magic happens when you can evolve how you're looking at the business.

Lauren Weinberg: Yes. I agree. And I think for us, too, just being really nimble and flexible. We're operating in a lot of countries, and if 2021 taught us anything, it's that different things are happening in different countries. There's been shutdowns and they're happening in all different times across the world. So I think we've learned how to be much more nimble and flexible as an organization, so if there's a shutdown in Australia but the UK is back in business, how do we start to really think about how we want to shift our investment? So we're paying very close attention to the data, really looking at all the trends so that we can be agile and really flexible and just responding to what's happening in the market in real time. And I think that's something that we had to get really good at really fast in 2020, but has continued throughout 2021, and I imagine in 2022, we're still going to be in a similar place of just paying really close attention to the data and figuring out how to best respond as a business.

Katie Foote: We always ask on our podcast what's the number one thing your team is focused on to help accelerate revenue? Would you say that measurement or driving lead gen are one of those things or is there something separate that really is tied to revenue for you this year?

Lauren Weinberg: I think those two things are hugely tied to revenue for us. I think for us, we're really focusing, back to your question on awareness, how long is the amount of time when we show awareness until we start to see customers come in so that we can just get better at modeling when we should see the impact there. So to me those two things go hand in hand, because obviously we're all about driving revenue as a business and all the things that we do need to tie back to us meeting our main key performance indicators, which are mostly around revenue from new businesses that we bring into Square's platform. So those two things are tied together. And if I had to pick a third, it would be just the awareness and consideration, just continuing to move in that direction. Which, again, goes back to how are we going to measure those things. But we know that there's so many businesses all over the world. And now we've entered three new markets in the last nine months, so there's a lot of education that we need to do and a lot of awareness that we need to generate to make those customers in those countries that have not really heard of Square before aware of all the ways that we can support their operation.

Katie Foote: Your awareness strategy is probably on a maturity spectrum. Some markets need to hear something a little different about your brand if they're familiar. Some people who are completely unaware of your brand are starting in a different place. It takes a different level of complexity to manage awareness in different markets.

Lauren Weinberg: For sure. And that's always part of our go to market strategy. So we're definitely a new market starting off with a little bit more of a brand message. Just hello, this is who we are. And then we start to get into a little bit more product specific. Versus in a country like the US or Canada, where we've been for a while, a lot of businesses are aware of Square, and then it really is about educating them on the products and solutions that we have to support them. So in that phase, we're much more interested in solution and product specific awareness and in driving consideration of those customers.

Katie Foote: All in the name of revenue, which is a rising tie that lifts all boats in a business. Well, Lauren, thank you so much for being here today and for sharing your journey at Square over the past four years. We so appreciate it and we are wishing you and your team the best of luck in 2022. We will be rooting for you.

Lauren Weinberg: Thank you so much for having me today. Katie great conversation, and best of luck to you and your team too.

Katie Foote: Thank you. Thanks everybody. See you soon.

Lauren Weinberg: Bye.

Katie Foote: Thank you so much for listening to Revenue Talks. We'd love it if you left a review wherever you're listening and hit subscribe so you never miss a new episode. You can connect with us both on Twitter at @ KatieJFoote, with an E, and @JustinKeller. And remember, revenue, it's everyone's business now.