John Rougeux: Bill, I’m thrilled to have you on the show today. Thanks for being with us.

Bill Macaitis: Thank you for the kind words, John. It’s an honor to be here.

John Rougeux: Alright. We have a lot of potential ground to explore today in terms of category creation. But before we dive in, Bill, could you start us off by telling us just a little bit about your background? In other words, who was Bill Macaitis before he started working with such high profile brands?

Bill Macaitis: I hate to admit it, but I’ve always been a little business nerd. I think it was in fourth or fifth grade, I was reading “Fortune,” “Forbes,” and “Business Week.” I’ve just always had a passion for business, and creating categories, and new enterprises. Certainly wasn’t doing it at that age, but I always had a passion around that. I think marketing was, for me, the nexus of so many of the different fun elements of running a business.

Bill Macaitis: Always was a huge into it. I just started up right out of college. Didn’t even know VCs then that would actually give you money to run your business. We did it the old fashioned way which was growing a business and an early SaaS subscription model. This was all the way back in ’96. It was a gaming website, and we were able to build three tiers of membership, profitable, sold it, spent about the next 10 years on the B2C side of the business. Went through a couple exits and then the last 10 was on the B2B side with the companies you had mentioned; Slack, Salesforce and ZenDesk.

Bill Macaitis: After 20 years of doing those operator roles and being fortunate to be involved in a number of exits, I made a career move and was going to go down the VC route, or the board advisor route. I chose the latter and it’s really fun. I get to work with other great startups now. I help them from an advisory perspective with their org design, with marketing tech stacks, with go-to-market strategy in it. It allows me to stay in the game which I love, but work with a great array of founders.

John Rougeux: Good stuff. Well, we’re lucky to have so much experience to tap into today. Maybe to start things off, could you share what you’ve learned about how B2B buyers make purchase decisions, in particular, what role do you see category playing in that process?

Bill Macaitis: I think in a lot of ways B2B mimics B2C. It’s maybe a little further behind but I think all of us can relate that how we research and buy products now are a little different than how we did it 20 years ago or even 10 years ago. You see people, at least on the B2B side, definitely researching, educating themselves about the company, the products, the pricing, the solutions. They’re doing a lot more research in advance before they talk to sales, if they talk to sales. They’re relying much more on peer recommendations. They’re using sites like [inaudible 00:02:56] Radius, [inaudible 00:02:57] does B2B reviews for these different SaaS applications.

Bill Macaitis: Not only that, but I think there’s maybe this misnotion that, oh, well if you’re in B2B everything is serious, and dull, and sterile brands. In my experience, people love to connect with brands on the B2B side just as much as they do on the B2C side. I think we all have, from our personal lives, experiences where we have that brand that we just love. There’s almost an emotional connection to it. We love the service or the product. We tell other people about it. We love interacting with that brand.

Bill Macaitis: I think there’s the same opportunity on the B2B side. I think that’s another shift I’ve been seeing in the buyer’s journey where people for brands that they really have an emotional connection with, you see the step function side effects where they just recommend you more, they buy faster, they buy more, they stay with you longer. I think that part of the buying process has changed, as well.

John Rougeux: What do you think has driven that? Is that from a buyer’s side in terms of expressing a demand for more, I guess, B2B brands with more of a personality? Or has it been that the brands that have succeeded have happened to be the ones who had that personality and that’s, thus, driven that trend?

Bill Macaitis: I think actually it comes from just consumers. At the end of the day a lot of people are selling to the CIO, or the VP of marketing, or the director of finance. But all those roles are people, too. A lot of them go to Amazon and see reviews for the products they’re going to buy. As I said, they’re like, hey, why can’t I see reviews for B2B software applications that I’m buying? Or they see brands that make them laugh or smile in the consumer space and maybe they say it the same way. Hey, I like that when I’m dealing with a B2B brand, too.

Bill Macaitis: I realize this is a hot topic and a lot of this is very controversial. A lot of people you talk to at B2B brand know we have to be put on our suits and ties and all of our pictures are stock photos of people around a conference table. But in my experience, I think that’s businesses of all segments; S&B, midmarket, enterprise. At the end of the day they’re just people and people, when they emotionally connect to a brand, they’re much more likely to do business with them.

Bill Macaitis: Who knows if that’s the chicken and the egg where some of the most successful companies that just invested in brand that’s why they become big, or was it just a side effect. I think it’s an easy differentiator for companies to stand out in a marketplace, especially when you’re creating a category and you want to really develop a deep affinity with your end users.

John Rougeux: Yeah. I know at ZenDesk branding and getting that personality right was really important for you. I think, if I’ve got these right, you defined the brand values there I think it was airy, humble, charming and uncomplicated. Would those values you came up with yourself? How did those play into your own competitive position?

Bill Macaitis: I think all the things that I did, that was a cross collaboration with people on my team, people on cross-functional teams within the organization. But I think for us at ZenDesk, you have to remember, support is just hard. It sucks. I ran support teams. You have people that call in and yell at you for 10 hours a day that have these problems. Most of the support solutions out there, before ZenDesk, were incredibly complicated. You needed a month of training. You would get sent an instruction manual that was a massive dictionary phone book. It wasn’t easy.

Bill Macaitis: Here along comes this concept of ZenDesk of just enabling zen, loving your help desk, simplicity, not complicated. I think a lot of, from just that overall theme we tried to embrace that, not having it be very complicated; so uncomplicated, airy, fun, humble, charming. It just was a very different thesis than a lot of the traditional providers, especially back in the day of with a lot of on-prem providers that were just selling straight into the CIO who never actually used the product and would just give it to the users, and the users were frustrated.

Bill Macaitis: For us, I think, that was just a great opportunity to differentiate. We use those values both from editorial tone and voice, but also just from a visual brand identity standpoint. ZenDesk, when you think about it, even in the early days, I mean, here you have this giant, green, this Buddha indicating zen. It was very different. It was very distinctive and a lot different from some of the other traditional players were using at that point.

John Rougeux: Do you consider ZenDesk to be a category creator, or were you simply playing in an existing category and that was more of a differentiation strategy?

Bill Macaitis: I think at the time ZenDesk customer service that’s been around a long time. These are always these debates with category creation. I think everyone wants to believe they are creating a new category. But in the same way, too, I do feel for the analysts, for Gartner and Forrester. There can’t be literally 20,000 different categories at some point. They need to combine the players together. ZenDesk, I think, where we embraced on a new category was this idea of just simple, easy to use, friendly, for anyone the team could come in and buy it. In the customer service space, at that time, that was pretty radically different.

John Rougeux: It was less about a new category of software but maybe more around a philosophy about the business and approach to offering software and working with customers, it sounds like?

Bill Macaitis: Yeah, exactly. Now I know we talked a little bit about Salesforce and maybe Slack and how we perceive them to be maybe in different category creators with different business models, or even how we took that. But I think for ZenDesk it was a lot about the interactions, the experience that you were having and in a different go-to-market model. I think that really helped us be able to differentiate.

Bill Macaitis: Also, even just this idea of, on the go-to-market model, staring off with S&P and then slowly moving the company up to midmarket and enterprise. For a lot of companies that just skipped that step and go straight to enterprise, at least I’ve seen. Some of the companies I talked to or even advised, if they go straight to enterprise, they kind of miss that step that says we got to make a really easy-to-use product that people can maybe buy frictionless, that they’re going to have an emotional connection with.

Bill Macaitis: Sometimes when you just go straight to enterprise, you lose a lot of that. You lose a lot of that brand essence. I think there’s a balance there, but for us, I thought that was really successful. Being forced to start off with small businesses and then moving more upmarket allowed us to, really we had to be good. We had to have a brand that people liked. We had to have a brand that people could start using and getting used to it quickly, and didn’t need a ton of support or customer success just to get them going.

John Rougeux: You mentioned Salesforce, so that might be a good segue to shift gears there. I know in that scenario, obviously, you weren’t selling to SMBs, the company was displacing on-prem software and delivering it over the cloud. Now when you joined, Bill, I think the company was about nine years old.

Bill Macaitis: Yep.

John Rougeux: What did the competitive space look like at the time and what were you doing to help to continue Salesforce’s unique position out there?

Bill Macaitis: When I joined, that was my first B2B business that I joined after my consumer run. It was really interesting because when I joined, maybe the company was about 3000 people. I came in and, to be honest with you, actually I saw a lot of maybe older school B2B marketing tactics being embraced. I think part of the reason they brought me in is they wanted to infuse a little B2C DNA, maybe innovate on the go-to-market model, focus more on the digital marketing side.

Bill Macaitis: Really what I tried to do is just bring us up to best in breed and really innovate on what could happen in the B2B setting. I invested a lot of resources, A, just on the marketing tech stack, making sure we had the right multi-touch attribution modeling, investing a lot in concept marketing, lead scoring, nurturing, doing a lot of multivariate testing, heat map analysis, but then also just building a really massive lead generation engine.

Bill Macaitis: Salesforce, we were constantly hiring and expanding the sales team. There was just more and more mouths to feed. I was really proud of what we did. We created just an amazing tech stack that allowed us to scale. We did really early ABM marketing before that was a big fad or a big strategy. We were targeting companies individually, saturating them, educating them, delivering content at the right stage. Then when our salespeople went in it wasn’t, “Oh, I’ve never heard of Salesforce before.” It was, “Oh, yeah. I heard about you.” Or, “I read this. I’ve seen you guys a lot in different places.” It really softened them and that allowed us to accelerate deal cycles, get larger deals that would close faster. It was a fun time.

Bill Macaitis: I guess, one of the things that always frustrated me was that when you would come into a company and I would see all these amazing SaaS products coming out. Then I’d ask a little bit more, “Well, what’s your go-to-market model?” And it was just a 30-year-old dusty B2B playbook. I just thought we should be innovating as much on the go-to-market side as we are at the product level. Whether that’s high-velocity, bottoms-up, premium models, concept marketing, SEO, ABM. The fun thing about marketing is it’s always changing and iterating and becoming more innovative. I wanted to embrace some of those and bring those into Salesforce. Over the four years, that’s what we did.

John Rougeux: I heard you mention in another interview that Marc Benioff was constantly repositioning the company, or rethinking the position. I’d love to hear a little bit more about that.

Bill Macaitis: First off, Marc is just, boy, what an incredible person. Just a philanthropist, humanitarian. He’s donated so much to these incredible causes. Just a great person, but also just this incredibly savvy business person, as well. I think what Mark was really good at was he just had a pulse on how to elevate Salesforce and really have it be about a mission. Even in the early days, Marc wouldn’t go out, and really what we were doing, we were selling sales automation software. You could go out and go, “Hey, guys. Check out this cool forecasting feature we have.” Or, “Here’s how you can calculate quota attainments.”

Bill Macaitis: But what he did is he really built a mission around no software. Just this idea of the SaaS model, the cloud model, which, thankfully, he invested in that because there’s literally 1000 SaaS companies now that can really thank him for building this model. At the time, people were really nervous about it. I mean, it was like, “What? You want us to take our most valuable customer data from our own servers and put it into the ‘cloud’ and ethos and it’s going to be surrounded with all these other customer’s data? What? Are you crazy.”

Bill Macaitis: I think as part of that, he was just constantly thinking about how we can fine tune into the positioning or messaging. We did a lot of events and Marc used that, actually, as a way to test out different messaging. When I came in, we put in a lot of the framework, where we could test that messaging on the site itself. There was one funny story we had where Marc, pretty much every year, we would evolve and iterate and innovate on the messaging. He had, it was very early, I don’t know what it was, something like eight years ago, and he really understood this shift to social. We were saying how it was disrupting all these different areas, the Arab Spring rising.

Bill Macaitis: We were launching this product, Chatter, he really believed in the social enterprise. Chatter was Salesforce’s messaging product at the time. We were all about the social enterprise and we’re going out at our conferences we’re doing this. Of course, all that messaging has to be everywhere so it comes out, hey, we need to get this on the homepage. We put it on the homepage, Salesforce the social enterprise. All of a sudden we start to notice our leads are dropping a little bit, we’re monitoring our bounce rate and our homepage and that’s going up. I’m like, “What’s going on here?” Right. We did this fivesecondtest.com. I don’t know if you ever heard of this. It’s a super cool site. You can just go, I think it’s five seconds. Five seconds, six seconds, seven seconds, five second-

John Rougeux: What’s it called a five second-

Bill Macaitis: The fivesecondtest.com. I think that’s it.

John Rougeux: Fivesecondtest.com, okay, got it.

Bill Macaitis: I’m going to look it up as we’re talking here. The cool thing you can do is you can, yeah, fivesecondtest.com. What they’ll do is, the idea is they will put up a homepage and they’ll have a panel that’s representative of your buyers. They’ll show you the homepage for, literally five seconds and then it goes black. Then they go, “Hey, what does this business do? What are they selling? What’s their value prop?” The idea is, hey, people, in general, you scan. You don’t spend 30 minutes on a homepage. We did this and we’re starting to get the results back. A lot of people thought Salesforce enterprise was, oh, we sell software for nonprofits.

John Rougeux: Oh, really?

Bill Macaitis: Like that’s what we did. Because they saw the social enterprise. That was interesting. I thought, actually, it was a really good use case of some of the more digital online marketing tools that were coming out that allowed us to make informed data-driven decisions based on what we were seeing for drops. And who knows? Because we’ve all had that as marketers. You see a drop in your leads and it’s like, oh, wait. Well, was it seasonality, or this competitor launched this, or our pricing change. Sometimes it’s a little bit tough to tease out what happened. But I thought that was a fun one as we were always evolving our messaging and positioning.

John Rougeux: I’ll have to go back into the way back machine and see if I can find the archive of that.

Bill Macaitis: It’s there somewhere.

John Rougeux: Well, a moment ago you mentioned the mission and this vision for the world that Marc was trying to sell people on, which was this idea of getting rid of on-prem software and all the headaches and costs associated with that and moving towards a model that was more flexible and easier to use, and really better for everyone.

John Rougeux: I think it’s really interesting. When I look at category defining companies, take something like HubSpot, for example, they have a very strong mission about making the process of marketing better for buyers and sellers alike. Inbound is all about that. As you were going through these different iterations of positioning, were you always coming back and referencing that core mission and that core story that Marc had developed early on?

Bill Macaitis: Yeah, certainly. I think this is when we’re, Marc loves the messaging and positioning side. He was always very close to it. We were always working closely with him on it. The same thing, he had a core set of values around how he saw the enterprise software space changing and sales versus role in that. Where I thought where he was really good, he would also just take the topical news of the day and really try to align Salesforce to that, and how we could reposition our mission so that we were in the news a lot and we got incredible coverage. I think that’s a fine balancing act, too. What is current? What are the larger macro themes that are happening? But also how does that relate to your core mission and how can you intersect those so that you do get the coverage, so you do get people talking about you, and you get the overall brand left?

John Rougeux: Yeah. Well, you’re in an advisory role now for multiple different companies. When you’re assessing the strengths and the potential of these companies, to what extent do you look at mission, do you look at story? A company’s ability to paint a picture of the future that’s bigger than just a set of features and specifications?

Bill Macaitis: Great question. For me, to be honest, what I look at with companies that I advise now is I look at it and just go, hey, is there a lot of pain in your space, maybe even latent pain? I often think with Uber, for example, there was a lot of latent pain in that space. I’m old enough that I remember taking taxis to the airport. I remember I would call Yellow Cab or something, it would be busy. I’d call Luxor, I finally get someone, “Hey, I need to go to the airport. Can you tell me what time they’re going to be here?” “No, we can’t.”

Bill Macaitis: I’m nervous they’re not going to arrive in time. Do I have to go to a backup? Then the finally do come but now I’m like, I don’t know if they take credit cards. What route are they taking? I had a lot of latent pain but at the time if you asked me, “Hey, what is the pain in your life?” I don’t know if I would’ve said, “Oh, taking a taxi to the airport, that’s terrible.”

Bill Macaitis: I always look for is there pain or latent pain in the space. I think at the end of the day, if you have a lot of pain in that space and you’re coming in and you’re willing to disrupt it, you can create a category around that. You can be a category-defining company. That’s a big area that I look at. I also look at, I just have a fundamental belief around this idea of customer centricity. Marc was a huge advocate for it at Salesforce. He always talked about the success of our customers and making them successful.

Bill Macaitis: I just know when I was a CMO for a while, I bought a lot of software. But it was a pretty crappy buying experience. I remember I would try to find, oh, I heard about this company. Okay, I go to the website. Sure, here’s a demo video but it’s like, nope, you can’t watch it. You got to fill out this giant form first.

John Rougeux: Right.

Bill Macaitis: Then, okay, all right, I fill out the form and I’m, literally, I get calls in the next hour and I’m like, “Sorry, I’m not ready to talk. I’m just learning a little bit about this space.” Then as I go through the sales process, I, literally, have 10 people selling me. They’re buying me steak dinners and doing all this wonderful stuff. The minute I sign the deal, I am assigned one-one thousandth of a customer success person to make me successful. I’m like, well, that’s a little odd, the ratios.

Bill Macaitis: If I did need support, it was five pages deep and it was a tiny four fonts customer support link and it would take three weeks to get a response from it. I’m just like, man, go to marketing and someone that’s buying something. Really it’s set up to just be a really bad buying experience. Can we innovate on that? I really love working with founders today that are open to different ways of going to market and taking a more customer-centric approach. Those are the founders that I love working with.

John Rougeux: I think you’ve certainly done that in your time at Slack. I think I’ve heard you mention elsewhere that the messaging for the company wasn’t just siloed from marketing and product. In other words, you had specific tone of voice and this helpful attitude that you wanted to convey on the marketing side. But then once people got into the product and they started using it, they found that voice was consistent, there were the helpful and fun product update notes and things of that nature. I’d love to hear more of that how you implemented that and what was the impetus of that in Slack because I feel like that among other things was a huge differentiator in the interoffice communications space.

Bill Macaitis: Definitely. When I had moved from ZenDesk over to Slack, again, I saw a space that, just a ton of pain. I didn’t know anyone that really loved email nor the other collaboration tools that were out at the place, there was just a lot of frustration around it. I thought we had an opportunity and I was excited to join because Stuart and the board really believed in this customer-centric approach, in creating an iconic brand that was different that was relatable and fun and whimsical.

Bill Macaitis: We had core values at Slack around things like courtesy and empathy. I had never seen another B2B company that had those. Usually it was all war terms, like we’re going to dominate, or destroy the market. Here’s this like, no, we want to hire people that are humble and have a lot of empathy and can put ourselves in our customers shoes and have a lot of courtesy.

Bill Macaitis: What we really tried to do was that works great when you’re a small team. I joined really early, I was the first marketer. My role eventually grew to where I ran the marketing sales success and support. That was great because really it was all the customer facing teams. It allowed us, then, to think about, hey, as we grow in scale how do we make sure that those core values come out? We did a lot of things like, A, codifying those core values. We had them everywhere. We had them on the walls. We had them as interview questions to tease out. Is someone customer-centric? Do they have the right empathy?

Bill Macaitis: Then we would codify them into our editorial tone and voice. Document it and train people that were writing anything, whether that was for marketing, or that was for support, or that was for sales. We would actually teach them the tone and voice and then even test them on it. Just think like, hey, same things with sales enablement but more from an editorial tone and voice perspective.

Bill Macaitis: Also, I think, just I was always really passionate that the brand is not just your experience with the product. It’s every single touchpoint. Again, when you go through B2B buying, a lot of those touchpoints are with these go to market teams, so sales support, success marketing. You’re actually having more interactions with them, at least initially, then maybe you are with the product itself.

Bill Macaitis: We really wanted to have a cohesive, fun, friendly brand. We didn’t use acronyms. We tried to just put a smile on your face. We tried to put that with all of the customer-facing teams and into the product itself, through the release notes, through the welcome message of the day, through the visual identity. The Slack had a very distinct brand. The colors we use, our logo. It was really all those to just always our North Star was around this overall experience that someone was having.

John Rougeux: I think that’s at least one of the reasons why Slack took off so quickly in that I know a lot of your motto was based on someone, the team being an early adopter, sharing with a few other people. It just being very lightweight and delightful to use. That would not have happened if you hadn’t really been intentional about making that messaging right and implementing that across the board. I’m curious, if someone is listening and they’re thinking about an initiative maybe like that or something that’s more brand related, maybe something that pushes the boundaries a little bit in the B2B space, but they have that idea internally, what’s your advice to succeed in that?

Bill Macaitis: I would just say, A, I think a lot of times when I work with companies or advise them, there’s sometimes a misplaced belief like, oh, well, in order for us to get big or different we have to spend a ton of money. Actually, I don’t think you need to. This is one of those areas, again, when I graduated from college and co-founded my first startup, we didn’t have any money. We were bootstrapping it. I think for you to codify a really unique editorial tone and voice, a visual identity, core values around customer centricity, those are all things that you’re not spending a million dollars to do. That’s just more an ethos, a core set of values, that you’re aligning around.

Bill Macaitis: Again, I like to zag when everybody’s zigging, zinging, yeah. If you look at most B2B spaces, or verticals, oh, my God, I don’t mean it’s kind of throwing them away but it’s so many of these products when you actually dive into the product itself, it’s black and white, it is sterile, lifeless. Every button is okay except next. There’s just no emotion. There’s nothing to connect with.

Bill Macaitis: I understand it, too, because a lot of times that’s dev and programmers that are writing this up but I think sometimes there’s this misplaced belief in B2B space that, oh, marketing, well, you’re just there to get leads there. Then you hand them off and sales is there to close them and then they go to product, and that’s just product.

Bill Macaitis: I think if you can take it from a more holistic standpoint and go, hey, if I’m on the marketing team, I have to think about that entire journey and thinking about the visual identity throughout the entire journey, the editorial tone and voice throughout the entire journey. Just the experience touchpoints that we’re having. It’s not like we did things, we just religiously measured and monitored net promoter score. We did a lot of transactional C-sat surveys. We’re always just trying to understand from an experience standpoint where are we providing great experiences, where are we providing friction.

Bill Macaitis: Ultimately, I would tell all my teams that, hey, your goal isn’t just to get someone just to buy from us, your goal is to get them to recommend us. I thought that was a higher bar and a harder bar. We really had to think about not just, okay, do we get them to sign up or pay us money, but, hey, do they love us to the point that they’re going to go and recommend us to 20 other people? That’s where in combination with sophisticated marketing, tech stack, and scaling, you’re going to get that crazy hypergrowth. That’s what I think allows you to ultimately have these category killers.

John Rougeux: You mentioned ethos, you mentioned messaging, you mentioned an understanding of visual identify. What other skills do you think are critical for marketers at companies that are developing new categories or aspire to develop a new category?

Bill Macaitis: I think marketing is always fun and challenging because you have this wide spectrum of the qualitative brand design side, to this quantitative data side. I’ve talked a lot about more the brand, the visual identity, the editorial tone and voice, but I think there’s a huge part which is on this data driven marketing. Understanding multi-touch attribution modeling. I think for a long time in B2B marketing, it was just either first touch or last touch. You’re letting that model determine where all the money goes.

Bill Macaitis: One thing that I have found out, spending a lot of time on this in Salesforce, and ZenDesk, and Slack, is people don’t just see your brand once and click and buy it. It can be 20, 30 touches over three to six months before they even become a lead. Then there’s another long period before they buy. You have to be able to model that out or work with the right software.

Bill Macaitis: I think you have to understand, invest and just the marketing tech stack. You can’t just throw bodies at problems. If you’re going to grow in scale you have to understand predictive leads growing, and multivariate testing and nurturing and content marketing and social media analysis. Even measuring brand, that’s a fluffy thing for a lot of people. But, really, for instance, at Slack we would measure aided recall, unaided recall, share of voice sentiment, share of conversation to really understand how we were progressing there.

Bill Macaitis: When we did launch these larger campaigns, how much did it cost us to get a point lift and awareness? I think you have to have the right blend there, and that’s where it can be sometimes challenging. Because I think people naturally fall into one or the other. But overall as a marketing team, I think you have to have the right rounded skill sets to have a comprehensive strategy to address those issues.

John Rougeux: You mentioned brand recall. That sounds like a skill that you may have brought over from your B2C days.

Bill Macaitis: Yeah, it’s funny because I think in B2B for a long time it was really, really expensive to measure brand awareness. Literally, they would send people to the airport and find decision makers and get them to fill out a survey, and cost you $100,000 every time you want to run a simple survey. Now, it’s really not that bad. You can use a SurveyMonkey or any of the different email tools out there. You can predefine your target demographics, the population, and then you can ask them the classic aided and unaided awareness questions. For those who don’t know it, it’s pretty simple. It’s just simply, hey, for instance when you think of team communication software, which brands come to mind? That’s unaided. You don’t give them any hints.

Bill Macaitis: Aided is, okay, when you think of team communication software, which of the following are you aware of? Slack, HipChat, Yammer, da, da, da. Then Sentiment just ask them favorability, extremely favorable to unfavorable for each of those brands. I think the fun thing is when you start measuring those. You not only get your own, but you get your competitors, too. You can start to understand. All right, well, what is the awareness for these other areas? Then, of course, people always overestimate their awareness.

Bill Macaitis: I remember when we first starting doing it at Slack, it was literally one of the first things that I did when I got hired on was I want a good baseline. Of course, at that time, and this was a while back, but everybody in the company thought, oh, yeah, everybody knows us and definitely because I’d see people on the street and they know Slack.

Bill Macaitis: But the minute I would fly anywhere outside of this little bubble of Silicon Valley, I would fly to the East Coast and be talking to some government people and a CIO for them and no one would know slack. I think, just again, doing the data allows you to take out this HiPPO, highest paid opinion, and just get down to the data-driven facts. It allows you to make educated decisions when you run campaigns, and you do these different customer-centric strategies to understand the impact on your brand lift, the impact on your net promoter score and just make a more educated decision moving forward.

John Rougeux: A tactic or an approach I haven’t heard you mention today is PR. But I’ve heard you mention elsewhere that at Slack, Stuart Butterfield’s story was exceptional and he was a great speaker, and PR was something that you guys invested in rather intentionally.

Bill Macaitis: Yep.

John Rougeux: How should B2B marketers assess whether PR is worth pursuing or not?

Bill Macaitis: At Slack, as much as I say I love all these customer-centric strategies, we did a lot of content marketing, PR. We did a lot of outbound advertising campaigns. We had our own podcast. We did a lot of traditional tactics. You need those to augment just your word of mouth. You need both to get you to that hypergrowth level. PR is one of those things, though, that I think you really have to look at a case by case basis. I mean, the reality is if you go to TechCrunch or Mashable or a lot of the tech pubs out there, 95% of the coverage is going to be around five companies. It’s going to be around Apple, and Microsoft, and Google. Every once in a while Slack will get in there, but it’s the big ones.

Bill Macaitis: Then you have 20,000 other tech companies that are scrapping for the remaining article. I think going in, you have to be really deliberate. PR is one of those feast or famine type things. You’re either going to get a ton or you’re going to get nothing. That’s why I think a lot of people get unhappy with their PR agencies and maybe unfairly, they blame the PR agency when in reality, you kind of have to understand, hey, is my company really that special? Or do I have a spokesperson that’s that special?

Bill Macaitis: It’s great Stuart did not mind investing the time into the reported relationships. He had a crazy backstory of growing up in Canada in the backwoods and forming two gaming companies that eventually pivoted into totally different types of companies. He was willing to take the time to do that. Whereas, I think, sometimes and there’s nothing wrong with this, I’ll work with a founder who is an incredibly brilliant developer roots but is more of an introvert, doesn’t like to talk to other people, and doesn’t have a really crazy backstory.

Bill Macaitis: I’m like, hey, don’t invest in PR. Don’t spend that 10 or 20K monthly retainer. We can use that in other places. I think you have to be realistic. Probably the number one determinant of how much PR coverage you’re going to get is your CEO. It’s not your agency. You just have to look at yourself honestly and go, hey, do I have a really unique story? Am I charismatic? Am I an extrovert? Am I willing to put the time into building these important relationships? If you are, then maybe you have a chance of getting good PR. But in general, it’s a really tough space to get a lot of PR for just an average company.

John Rougeux: I think that’s great advice. PR is one of those things it feels good to get your company mentioned in certain publications and the attention always makes you feel proud of yourself, but I think you make a good point. If the story really isn’t there and if it’s not something natural, and you don’t really have something special to say, then maybe it’s worth reconsidering pursuing that or not.

Bill Macaitis: And it’s also, and, again, I have nothing against PR. We’ve used it really well at Salesforce and Slack, but it is one of those 20-year-old, 30-year-old traditional B2B tactics. I just think, hey, it may still work and there’s definitely a place for it, but that should be, I think you should look at it at a holistic level and think about, hey, how are we innovating in these different core areas?

Bill Macaitis: What are we doing for content marketing? What are we doing for predictive lead scoring? What are we doing for ABM? Just every year something new comes out in marketing. The technology advances, or there’s different ways to measure different things and allows you to embrace new tactics. I always advocate when I work with different founders of, hey, as incredible and innovative as your product is, let’s make your go-to-market model that. Let’s make it a differentiator, and let’s allow you to grow in scale faster and define a category, and dominate it. I think if you take that same mentality and approach it to all your different marketing areas, you’re really going to be able to move the needle.

John Rougeux: Bill, with your perspective as an advisor now and being able to look at the whole B2B space from the 50,000 foot view, what are some examples of category-defining companies you really admire right now?

Bill Macaitis: Sure. Well, there’s one that’s been a North Star for me for a long time is Amazon and Jeff Bezos. Not only that, because I think 1% of the revenue comes from my household, the amount of stuff that me and my wife seem to order and amount of packages that show up. But also just, I think, Jeff is a classic example of just insanely customer centric. You hear these amazing stories that come out of the company.

Bill Macaitis: I love one that’s around for every meeting they’ll leave an empty chair and that chair is the customer. At the end of the meeting you go, hey, would the customer have liked whatever our decision was? Because ultimately as the company grows in scale a lot of times, you just focus on a more internal mechanics and you don’t really think about what is the impact on the customer.

Bill Macaitis: I remember one, this was an example of that, when Apple launched their own maps which came out to a lot of interesting, their launch strategy. But one of the things they did was Apple inherently defaulted everything to the Apple Maps. I love Google Maps, I just have used it for so long and I love the product. It was really frustrating to me. That was a great example that wasn’t a customer-centric decision. That was something that was, I’m sure was internally debated and said, “Hey, we need to build up our own. It doesn’t matter if it’s a bad experience or if Apple Maps isn’t that good to start with, we’re just going to force everyone to essentially use it.”

Bill Macaitis: Those have impact. It was even something going on a little bit of a tangent but even thinking about Slack when we came out. One thing we were always really deliberate about was any type of biz dev or integration thing, we always want to think about the customer at the end of it. Slack, over time, we launched our own video conferencing and audio conferencing and screen share but we still, you could use anyone you wanted. You could use Zoom, you could use any of the dozens of video conferencing. We made it really easy.

Bill Macaitis: I just think that idea of customer centricity. A lot of that, for me, I was always inspired by Amazon. I think you’re seeing more and more companies now that are really trying to look beyond just the short-term metrics of how many leads did we get or what was the sales that we closed to think more long term of, hey, well, these people, you got to think about lifetime value and Slack naturally makes you think about that. But even going beyond that.

Bill Macaitis: Well, what if this one person recommended us to 50 other people? Maybe that lifetime value should be a little higher. Maybe we should think about the experience in getting them to recommend us, or even having a brand that differentiates and that they love. I’m always inspired by other customer-centric companies out there. I give kudos to all the founders that have the courage to go down that path.

John Rougeux: Why do you think we’re not better at that in the B2B space, Bill? Do you think we don’t have the skills, or other people we have to report to don’t care about it, or it’s not valued or measured? What’s holding us back?

Bill Macaitis: If you talk to most CEOs, I think everyone will go, “Yeah, we’re about the customer.” I haven’t met many CEOs that don’t say they’re not about the customer. To be honest, I think what happens is in the Silicon Valley, it really starts with the VCs. You have so many companies that are being founded and there is such an obsession with short-term metrics, that all the focus is put on these short-term metrics. How many leads did we get in? How much ARR did we close?

Bill Macaitis: I think it’s a little bit harder to go and say, “Hey, you know what? As opposed to the short-term metric, let’s look a little bit further out. Let’s look at more, for instance, that promoter score as more of a leading indicator of how much people love us.” Another thing Jeff said at Amazon, which I always believe in, too. He said, “For any company, there’s inputs and outputs. Outputs are your revenue. How fast you’re growing.” But when Jeff would go into the year, he wouldn’t say, “Well, our target for revenue is this amount this year.” Or, “We want to sell this much product.” He would go, “Hey, let’s focus on the inputs.” The inputs for Amazon were lower prices, and faster shipping times, and better product depth and breadth.

Bill Macaitis: Those were the inputs to get you those great outputs. In the same way, I think, for companies that recognize that, hey, giving a great experience and measuring things like transactional C-sat and net promoter score and thinking about that experience gives you the output of faster growth. Ultimately, I think it’s a combination of all those things. It’s a lot of, it’s insanely competitive. There’s so many startups out there. A lot in the VC space put more weight on your short-term metrics and that forces the CEO and the operating team to look at those metrics.

Bill Macaitis: It’s tough, it’s tough. You need that next round to finance it, financing, you’re going to be more weighted around there. But I really believe when you have this combination of a board that believes in long-term customer centricity and operating team, and you hire people. Like Slack, all right, we hire people that are around customer centricity that had empathy, that had courtesy. You get more of this holistic customer centricity company. That allows you just to get these crazy word-of-mouth referrals and you get that incredible growth rate.

John Rougeux: That’s interesting you mentioned Amazon as that example of shareholder expectations because if I recall correctly, Jeff, pretty early on, set expectations around the company being a long-term play. They might need to be prepared to have to lose money for several years as they built that. Obviously, not all of us are in that position to directly influence our investors and our board, but I think that’s great advice, whether you’re starting a company, looking for funding. Or if you’re looking to join a company, it’s not just about the product but it’s about the people who are providing the backing for the company and the way they view things.

Bill Macaitis: That’s one of the things that, when I work with companies now in the advisory capacity, and I think I’ve tried to help them out with is like, hey, let me connect you to VCs that believe in customer centricity, that have a longer-term outlook. Because there are great ones out there that do believe in that. I think that at the end of the day, most operators, they’re not satisfied with just making a tiny company. They’ve got a great vision, and most founders have a long-term outlook. If you can get all the different pieces in place, I think you’re in a much better position to embark on a strategy like that.

John Rougeux: Good stuff. Well, Bill, we’ve spoken at length, but I feel like we’re just scratching the surface. But we’re getting close to the end of our time. I just want to ask you one question that I like to ask all of the experts that I meet with. If one of our listeners is interested in exploring more about category design, B2B branding, what are some resources that you recommend?

Bill Macaitis: Obviously, you have this incredible podcast, and I think it’s always great to go through the archives there. Personally, I love podcasts. I follow them myself on the road a lot and in traffic a lot. Podcasts for me were a great opportunity to learn a lot about different spaces, different opportunities. I like the, there’s some great podcasts out there that I always like to stay on top of. Things like “Marketing Over Coffee,” if I’m thinking about my marketing skills. If I’m thinking of my manager skills, I like “Manager Tools.” I think that’s a great one out there, “Economist.”

Bill Macaitis: I think ultimately we can talk about category creation in a very 10,000 foot level, but really what it comes down to is execution. It’s all these little blocking and tackling areas of building a customer-centric company, building the right marketing and tech stack. Having the right dimension funnel, building the editorial tone and voice. I think anywhere that you can find either podcasts, conferences, people that are passionate about building best of breed specs in those areas, that’s what’s going to allow you to grow and expand and, hopefully, create and dominate your own category.

John Rougeux: Good deal. Bill, if one of our listeners wants to get in touch with you, what’s the best way for them to do that?

Bill Macaitis: Just contact me on LinkedIn. Shoot me a note. Happy to talk. Always enjoy conversing with other passionate people around the space.

John Rougeux: Yeah, I can vouch for that, Bill, because you’re one of those people who’s accomplished so much. But I think I sent you one LinkedIn message and you responded. In think in 30 minutes, made my day.

Bill Macaitis: Good deal. We’re all in this together. I mean, it’s one of the reasons I enjoy advising companies now is it’s an opportunity for me to just reach out and talk to other people that are also passionate about building their own categories and sharing them both the wins as well as the heartaches of what I’ve gone through. I love working with other people that are passionate that maybe want to do it differently in a customer-centric way. Like I said, feel free to hit me up on LinkedIn. I’m always happy to talk and go from there.

John Rougeux: All right. Well, Bill, thanks so much for being with us today. It was great having you.

Bill Macaitis: John, it was such a pleasure, man. I really enjoyed the topics. Like you say we could’ve gone on for a couple hours on these but I know most people don’t have that long of a commute so hopefully this fills up their commute quite nicely.

John Rougeux: Sure thing.