As we’re increasingly inundated with AI-generated content and algorithm-driven ads, what’s more powerful: yet another new technology, or the authentic voice of the small business owner on the corner?
Agility requires not just reacting to market shifts, but deeply understanding the very fabric of the communities you serve and having the conviction to amplify their voices over your own. It’s about finding strength not in shouting louder, but in listening closer.
Today, we’re going to talk about how a brand can cut through an increasingly crowded market by turning its most loyal customers into its most powerful advocates. We’ll explore the strategy of reasserting brand relevance through authentic, community-driven storytelling, and what it takes to execute this when competitors are focused on features and scale.
To help me discuss this topic, I’d like to welcome Lindsey Irvine, Chief Marketing Officer at Square.
About Lindsey Irvine
Lindsey Irvine is the Chief Marketing Officer (CMO) at Square, the technology company that makes commerce and financial services easy and accessible. With nearly two decades of experience in marketing, strategy, and leadership across both large enterprises and fast-growing startups, Irvine is responsible for overseeing Square’s global marketing efforts, driving brand awareness, customer engagement, and market growth around the world, all in service of the company’s mission to empower businesses and entrepreneurs worldwide.
Before joining Square, Irvine was CMO at Benchling, pioneer of the R&D Cloud powering the biotechnology industry. Prior to that, she spent nearly a decade at Salesforce, where she held several leadership roles, including global CMO for MuleSoft, and played a key part in developing go-to-market strategies across IoT, industry verticals, and cloud solutions. She is credited with driving high-impact global marketing strategies and helping position Salesforce as a leader in the enterprise software space.
Lindsey Irvine on LinkedIn: https://www.linkedin.com/in/lindseyirvine/
Resources
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Transcript
Greg Kihlstrom (00:00)
As we’re increasingly inundated with AI-generated content and algorithm-driven ads, what’s more powerful, yet another new technology or the authentic voice of the small business owner on the corner? Agility requires not just reacting to marketing shifts, but deeply understanding the very fabric of the communities you serve and having the conviction to amplify their voices over your own. It’s about finding strength not in shouting louder, but in listening closer.
Today we’re going to talk about how a brand can cut through an increasingly crowded market by turning its most loyal customers into its most powerful advocates. We’ll explore the strategy of reasserting brand relevance through authentic community driven storytelling and what it takes to execute this when competitors are focused on features and scale. To help me discuss this topic, I’d like to welcome Lindsay Irvine, Chief Marketing Officer at Square. Lindsay, welcome to the show.
Lindsey Irvine (00:51)
Thanks, Greg. It is awesome to be here.
Greg Kihlstrom (00:53)
Yeah, really looking forward to this conversation and looking forward to diving in before we do though. Why don’t you give a little background on yourself and your role at Square?
Lindsey Irvine (01:01)
Sure, happy to. So C-Mode Square, I’ve been here for a little over a year. It has been a wild and awesome ride. I’m sure we’ll into it. Prior to that, I’ve been about over two decades in marketing and go-to-market more broadly for tech companies. So I was almost 10 years at Salesforce, held a variety of different kind of go-to-market roles, was the CMO of one of our business units, MuleSoft when I left, and then transitioned to actually help run and grow a startup company called Benchling, where I was also the CMO. So spent a lot of time focused on the software and technology world. And it’s been a really fun year putting all of that to work for small and local businesses.
Greg Kihlstrom (01:39)
Great, great. And I think most people listening are probably familiar. I’m positive they’ve come into contact with Square before, but could you give ⁓ maybe the big picture? What’s Square’s core focus today and who are the customers that you’re ultimately trying to serve?
Lindsey Irvine (01:56)
Well, probably a lot of the listeners like me think of Square as that little white reader that we all saw on the farm market, you know, 16 years ago when it got started. And I think it was such a powerful concept, which is how do we let anyone with a dream, any entrepreneur with an idea, how do we make it incredibly easy with that white reader for them to start and run their business by democratizing payments? Fast forward, Square serves over 4 million businesses around the world.
And we are not just that little white reader that you think of from farmers markets. It’s in addition to kind of being the point of sale in every neighborhood. We also have a full software platform. We offer banking services. So businesses can take out loans through Square. We have checking services as well. And we have a full range of solutions for a business to operate and streamline how they run. So it really is a full service kind of local commerce platform.
Greg Kihlstrom (02:48)
Yeah, so let’s let’s dive in then. And we’re going talk about a few things today. But I want to start with something I touched on in the intro. And this is really, you know, brand strategy in a crowded market. And Square’s recent see you in the neighborhood campaign is a clear bet on local businesses as brand advocates. So with competition in a lot of spaces and fintech and the payment space intensifying
What was the strategic insight that led you to double down on community voices instead of a more traditional feature focused or a tech forward campaign?
Lindsey Irvine (03:23)
Yeah, it’s a great question. I would say there’s two main insects here. One, you need to start by deeply understanding who your customer is and who you’re looking to serve. And the second is look to develop content and leadership and activations that actually speak to those customers in your community far beyond product and feature functionality. So just to go back to the first, like deeply understanding your customer.
We’ve always grown up as being for small business, but as we actually dug in to the breadth of Square customers today, what we actually realized we stood for is not just small business, but local business. And that could be the mom and pop who opened their single store on the corner. It could be a 60 to 100 location business like Bluestone Lane that’s scaling nationally. But what they all have in common is they’re more than just
a restaurant or a coffee shop or a salon, they really are part of their local community. Right. And that is a key reason why they started. That is a key factor to their growth. So we really at the center, we’re for the local business, not just the small business. And then the second was, okay, how do we really put local businesses up on a pedestal? Right. And our campaign platform is see you in the neighborhood. It’s far more than a tagline. That is our promise in terms of we’re actually from a marketing standpoint going to show up.
and put investments into local communities and into local business to support both our sellers, but the communities around them, like grow and thrive. It’s a promise that every element of our campaign actually heroes and spotlights the real local business owners and not our words, their words, their stories, their journey. And the through line is certainly how Square is a part of that journey and a part of their growth story, but it really heroes the local business through it all.
So I think it’s, it is both, those are the two key insights is know your customer deeply for us, it’s the local business. And then make sure that as you’re developing a brand campaign, a platform, really find ways to speak to and authentically represent the heroes of the story.
Greg Kihlstrom (05:27)
Yeah, yeah. And I mean, that’s such a key part of the brand strategy then. And, you know, another part that I know you’ve spoken about is just maintaining and reasserting brand relevance in this era. What does relevance mean to you and the brand? And how has that maybe how has that definition evolved from what it might have meant for a company like Square five years ago?
Lindsey Irvine (05:50)
Yeah. I do relevance to me at its core is delivering on your promise to support your customers, to actually show up and be there for your customers. And then definitely to deliver the products and the innovation that help them be successful. think without any of those three, you’re not going to be truly relevant, right? You can’t just be a brand and then not deliver the product value and you can have product value and only talk feature function and not actually show up in times of need or when there’s questions.
So I think that that is what real relevance looks like and how that’s evolved for Square as part of our brand promise of seeing the neighborhood is we are both putting the real humans of Square to work for our local businesses. So we have local representatives in neighborhoods across the country and across the world that are literally walking the neighborhood and showing up for our customers, both existing and new, there to answer their questions, offer support and really be there, be a trusted advocate for the local business and what they need. And that’s really been valued. So there’s a people component to this. There’s a product component to this, right? Which is we actually just hosted our second kind of bi-annual, we call square release. It’s our twice a year, big product moment where we bring big innovation to life. And it’s all shaped by our local business customers, right? What they need and want. And so we just unveil a lot of new product innovation together, bringing the community together.
and the feedback was overwhelming. So that’s the second thing is like delivering the innovation to stay relevant and frankly stay ahead of where your customers are asking you. And then I think the third thing that’s really sparked by this campaign is we’re not using like flashy celebrities that don’t tie to our brand to try and create relevance, right? Like we are literally the center of our campaign, our TV spots, our ads. The full thing is we’re hering real local businesses who by the way, are celebrities in their own right, in their own neighborhoods. And so it’s kind of a flip of the table of using local heroes, local influencers that are actually the business owners that we all know and love in our own communities and giving them the spotlight to tell their story.
Greg Kihlstrom (07:58)
Yeah, yeah. I think you’re touching on the authenticity part of this as well, which is, you know, again, I think a lot of a lot of brands use celebrities and it’s, you know, there’s there’s an approach there. But, you know, using real people, real voices, real people within their their communities definitely lends to that authenticity. But, you know, as as anyone knows, it’s hard or it can be hard to do that at scale. And, you know, how do you how do you go about
identifying and finding, you know, the right stories that are relevant and really serving that brand narrative while keeping, you know, keeping it real for lack of a better term.
Lindsey Irvine (08:36)
So I think this is where brand also has to tie to business strategy, right? Cause you can find some really cool influential, you know, businesses where customers represent, but if it doesn’t tie to where you actually want to feel growth, you know, it’s, less. And then it’s also how you tell their stories. So I think tied to that on the business strategy piece, the first place we started before identifying the right sellers to hero before working through the campaign specifics was what are the cities and neighborhoods where we think we have the most opportunity?
to both be helpful and to continue to grow, right? We have a good existing base, but we also have a ton of opportunity. And we did that in both the US and in our key global market. So I think that’s the first thing. And importantly, that’s not just a marketing investment strategy. That’s where we’re putting real humans of Square to work in those cities and neighborhoods to make sure we have people representation. So I think that was the first thing is we got really clear on the key cities and the actual neighborhoods in those cities where we saw real opportunity to both show up in authentic ways, support existing customers and grow. So what that all does then do is identify the local businesses that are square customers today. They’re really influential and local heroes in their own right in those cities and in those neighborhoods. And that’s the exercise we went through, right? We kind of looked at both who our customer base was there, who are the sellers that are the real heroes in their community. One interesting fact is we found very often it’s the restaurants at the center of their community that really create the meeting points and the gathering points. So we tried to recognize that and spotlight some of the really great restaurant owners in their communities as well as other business owners. That was the approach. And I think importantly, that led us then back it up, not just by highlighting those influential real sellers in the community, but then really surrounding them with the full power of Square. And the idea part two is no one wants to listen to a scripted customer talk, right? Sounds like the vendors giving them all the words to say and it feels very, very faked. So our approach with our creative team is as we identify these sellers, we go on site, we go into their actual business, we compensate them for the time, by the way, if there’s hours that close down and we actually also bring the community together afterwards. And we literally, we give them some questions, but we let them riff and tell their own story in their
So there’s no script. There’s no, have to say these things. It’s here’s the questions we know the community is looking to understand. Say what is true to you. And as a result of that, you get just, think really compelling, authentic, truly community relevant content where people are interested not just in watching it, but now they want to go to those people for advice.
Greg Kihlstrom (11:13)
And so, you know, I’m sure there are some, you know, what you’d call traditional measurements and, you know, marketing measurements that you’re using for growth and other things like that. But, you know, how does this approach, does it change? Does it add new types of measurements or just different ways of looking at success when you’re getting so involved in communities and looking at things like this? Like, what does measurement look like, in other words?
Lindsey Irvine (11:37)
I’m gonna take your question as the classic brand versus demand. I that there are a few ways and I do think it’s incredibly important to tie your brand investments to the company metrics, right? And to what your stakeholders care about. I also think I’m going to come back to that in a world of AI generated content and AI bots and kind of AI slop everywhere. Brand is the one thing you can’t fake.
Right? Or you can’t, you can’t AI your way to real brand connection, real human connection. and so I think that there is a feel to the brand. There is a vibe. Like you either have a brand that people feel like is of the moment and culturally relevant and they’re paying attention to it or you don’t. Right. And so I think that’s just the first thing to acknowledge is in this world of AI generated content, people are acknowledging that metrics aside, you need to invest in real.
human connection, real customer connection, and a brand that adores and stands out because that is your moat. And without that, you’re one of many. Now, to get back to the metrics question of how do you actually then measure this outside of the classic awareness, perception, consideration shift. I think there’s a few key things I look at that tie back to the company care abouts. So the first thing is revenue growth, right? Revenue growth also equals long-term pipeline growth. Brand, undoubtedly,
creates long-term pipeline growth. And here’s how, 95 % of your buyers, and this is proven by number of studies, are not in market to buy at any given time. So all of your performance demand dollars are going to the 5 % that are ready to click by now. 95 % are not there yet. So Brand allows you to reach the 95%, create interest, create excitement, create authentic connection, and be in the consideration point when that 95 % becomes the 5 % ready to buy. Because the other data point is every one of those buyers buys on the top three what brands come to mind first and are in their top three consideration list. And typically they’re first and that is brand. That’s the awareness, that’s the connection. So that’s the first thing is brand and you can prove this over time, but brand actually equals long-term pipeline growth because you’re acquiring and building engagement and resonance with the 95%.
I think the second way I measure this, which is more tactically is, okay, if you’re doing that, then you should be able to see growth in your organic traffic, right? And we know organic traffic converts better than paid traffic. So that’s another very, very clear way you can measure this is if you’re doing a lot of brand work and it’s resonating, more people should be organically coming to your own properties, right? So you can look at a lift in organic traffic. And then there’s a lot of clear data that says organic performs better than paid.
from a conversion standpoint makes sense. So then actually you start to see the flow through in real revenue, right? More pipeline builds. And then there’s also good results is if you actually look at brand investment done right, you will see it an increase in your paid performance spend as well. So I think those are some of the key areas I look at other than if you know, know, you know, your brand is at the moment and culturally relevant or it’s not. And that is increasingly a moat in an AI world.
Greg Kihlstrom (14:47)
Yeah, yeah, love that. So I want to talk about I know this isn’t your first CMO role, but you know, at Square, you’re about a year into into your role. As you said, what has been maybe the most surprising or most valuable lesson you’ve learned about leading a well known brand like Square through this kind of strategic evolution?
Lindsey Irvine (15:09)
I’m going to give you two big surprises. One is always stay building and always stay curious. I think from the outside in, you would think that we’re a large public company. We have 4 million customers. We have a very large product portfolio. We’ve got it all figured out. I firmly believe companies of this day and age need to act no matter the size or scale, like builder startups. And I think that’s what’s incredibly cool. And what’s frankly surprising to me is the startup mode that squares in, you know, and really that builder first mentality. We are all builders here and we’re using AI to support that build mentality and to do a lot of work that’s increasing velocity and value to our customers. But I think that’s the first thing is just you got to be a builder, right? And man, even at this size and scale we’re building and we’re putting a ton of good pressure on ourselves to increase velocity, ship faster and deliver more value to our customers and find more ways to just get more out of the work we’re doing. So I think that’s the first, which lends itself to having to be constantly curious about new things to build and new places to go. And I think the second thing is Square has such a phenomenal brand and such phenomenal brand awareness. But what was surprising when I joined was how many people still think of Square as the little white reader. So people still harken back to like, yeah, you guys are the thing I can…
plug into my phone and then I see it every farmer’s market. It’s like, yeah, and, and, and, and, and, right? We have this whole portfolio of products and services. And when people get exposed to that, they’re like, whoa, they’re thrilled. They’re amazed. They’re also like, I had no idea. So I think that was the second surprise point that is we have such a rich product portfolio that adds a ton of value to our customer base, but many of them don’t know about it.
And so that was both part inspiration for the brand, but I think importantly, part inspiration for how do we be much more deliberate about being clear of the value we can provide. And as we launch new things, creating emotion, which we now call square releases, where we can really bring the innovation to life in clear ways for our sellers each and every year in every market. So they know and start to expect like, this is when I can go find out about what’s new and start to take advantage of that.
Greg Kihlstrom (17:21)
Yeah, yeah. Yeah, I don’t know. Maybe that’s it’s like anchor bias or something like that. You know, the the people thinking of of square is that that thing they saw, you know, five, five years ago or so. But I mean, I think that’s another that’s another challenge, right, is being able to overcome and build on, you know, build on those things. And I, you know, people in this case, it’s a positive, you know, it’s it’s a positive interaction, but they get this this thing in their mind. You know, how do you
I guess what’s the best way or best first way to help people kind of understand that yes, you are that but you’re also so much more.
Lindsey Irvine (17:55)
Yeah, it’s a great, I mean, this is the, I feel very fortunate. We don’t struggle from a brand awareness problem. Right. And perception challenge, right? It’s the perception shift that we need to drive. So I think again, that it comes back to like, so where do you start? You’re like, okay, well, we can serve a literally any business in any part of the neighborhood, in any city around the world. That’s a very broad surface. Yeah.
How do we start to create moments that matter for that broad surface area to come together and learn about what we have to offer? So that was the first, and we do that through our twice year square releases. We’ve now launched a What’s New webpage, right? Where you can actually come and literally every month see new features that are added and get a preview of the roadmap. And now every month we’re sending out to our different sellers by audience type.
a proactive here’s what’s new and here’s what’s coming. So I think that’s the first thing is we have such a wide base. We want to make it really easy for sellers to find out what’s new and they’re hungry for it. So I think that’s the first thing. I think the second thing is I am a big believer in brand. is not your way to pitch features and functionality, right? So see you in the neighborhood will never be let me tell you about our whole product portfolio, right? It is much more about again, elevating the voices of the community and telling their stories. And underneath that then, you have to really have ways in which you pull through on more of that. Okay, that’s cool. So now what do you offer, right? You have to then really be able to pull through on the product value prop. And so that’s where we in marketing speak, do have a series of campaigns where we actually, they’re much more mid funnel oriented where once someone is interested in learning more or how can Square help me.
We proactively are targeting certain types of sellers with a clear product value prop to expose more of what Square has to offer. And then the last tech Othino will give you, you would be amazed at how far a really great simple product demo goes. People just want to click through on their own. And if you’re lucky, like we are to have a genuinely intuitive, easy to use product, the more ways you can get that out in the world and get that in the hands of people physically and virtually, the better. So I think that’s just the other way.
I predict a few of the big topics we and more broadly, like a lot of people will be talking about is how brands continue to stay relevant in this world where AI starts to intermediate the customer journey, right? And the customer experience and how you allow your brand to show up and create genuine human real connections, right? And also,
how your brand shows up for the AI agents that are crawling for all this information and feeding first principle knowledge to what should I choose when I’m thinking about XYZ? So I think brands are increasingly, I think the conversation here from now will be like, how does a brand do both well? How does a brand show up for real for humans? And then how does a brand also in a very distinct way show up for the AI agents that are now frankly a customer we have to serve and solve for. So I think that’s probably the biggest one. I hope the other side of that conversation is on the first part, the human connection. Like how are we being able to be so authentic and fun and interesting with our brand building and customer base? And I think that’s an opportunity we have. People wanna have fun. want real, they want things that feel authentic and real and gritty at times.
And I think you’re going to see a lot more of that from us as we look forward because we’re really, we have such an incredible base of real businesses that we get a pull from and excited to just have fun with it and authentically show what’s up with what it means to build a business.
I’m sure there are things you haven’t thought about, so there you go. I am constantly talking to as many people across the org as I can, not just my directs, but like tons of skip levels and different conversations and also traveling quite literally the world to meet with our customers. So I have innate first principle understanding of the problems we’re trying to solve. And that I’m constantly looking to also acknowledge what we’re learning and where we’re failing, not just what we’re working. Cause I think part of being agile, is not just plowing forward, but it’s taking time to what are we learning, what’s working, and importantly, what’s not working, and being open and vulnerable so you can quickly course correct. And I believe that matters now more than ever, given the fast-paced nature of what we’re all working in.
