Today on built to stay. We looked at like kind of these free plans in these free users as these were incredible, you know, marketing evangelists for us and they were going to help spread the word about what Slack is and what messaging is and how it can make your company more efficient and more productive. And that was really helpful. Welcome to build, to stay a podcast dedicated to sticking, staying and succeeding in the business world from the blip sound lab. Here’s your host, Bart Bradshaw. Hey builders, how many of you have used Slack before? We use it a blip. And for all sorts of companies, Slack has revolutionized the way we collaborate at work. Today’s guest, Bill Macaitis built the marketing playbook for Slack, which helped them become the fastest growing SAS company in history by leading all customer facing teams. He developed the iconic customer centric brand that Slack is today. And before that he was a CMO, customer service software Zen Desk and help lead them to a $1.7 billion IPO. So if that’s not enough, bill helped grow Salesforce revenues from 900 million to 3 billion in just a few years. And this is all the say. Bill Macaitis knows the ins and outs of marketing. And today we’re honored to hear his story and advice. Bill, thanks for joining us today.
Bill Macaitis: (01:15)
Well, it’s an honor to be on. Thanks for having me.
Absolutely. So you’ve been instrumental in helping three of the fastest growing SAS companies of our time, most recently Slack, but you didn’t start out working for, you know, others you started out on your own. So a lot of people go from successful employment to building their own startup, but you did it the other way around. And I’m wondering, do you think of yourself as an entrepreneur?
Bill Macaitis: (01:42)
I hope so. I think so. Yeah. I’ve always loved business. I mean, I was the nerd in the back of the class and you know, fifth grade reading, fortune, Forbes, and business week. Um, I always had a passion. I always knew I wanted to be part of businesses, start my own business. And yeah, the, the first one we did out of college, I cofounded a site with, uh, four other people and uh, you know, we’re a little dumber back then we didn’t know there were things called VCs that would give you money for a portion of your company. So, you know, everything was bootstrapped. And in a way I thought that was great because, you know, I took a lot of the same learnings and I think, you know, if you look out in the world today, there’s so many small, medium sized businesses that don’t just have big budgets, right.
Bill Macaitis: (02:22)
You have to do it kind of on the cheap and do things that scale and make efficient. So yeah, that first startup experience where we had to use all of our own capital, um, and trust me, didn’t have a lot of capital. Uh, that was a great experience and we grew it to 10 million members. We are profitable mostly because I thought that’s what you’re supposed to do coming out of school was let’s have a profitable, it wasn’t as though we have all these eyeballs. Right. It was like we had to make a profit, you know, we had a three tier subscription plan and we had advertising revenue. Um, but it was a great experience to go through and it definitely taught me a lot.
Yeah. And you really learned, you know, on the ground how to do marketing in this kind of newer digital online world.
Bill Macaitis: (03:03)
Yeah. You know, it just felt like, you know, the world was kinda changing and, and how people were connecting and finding out about things. And, um, but even back then though, you know, one of the primary reasons our, our site grew. It’s just word of mouth. And w we made it easy. We incentivize people and we had referral systems and all this. But, you know, still, um, I’m a big believer in any marketing playbook. You’ve got to start with just this customer centric, uh, philosophy where you just delight people in every stage, right. And, and, and you hope that they have a great experience with you and they go recommend you. And you know, ultimately I think like a brand that stands for like, Oh, it’s a slogan or a logo or it’s your visual identity. To me, like a brand is just, it’s the sum of every little experience that someone has with your, with your, with your company, right? And that’s just not the product. That’s your marketing experience and your sales experience and your legal experience and you know, all these little micro experiences, can it get to the point where people are either going to go out and recommend you or they’re not? And so, um, that, that was a, you know, a philosophy we tried to embrace early in that startup. And it’s something that I’ve always tried to think about for the other companies that I’ve worked with as well.
Oh, that’s awesome. I love that. A perspective, that philosophy. Um, and you know, whether it’s digital online or you know, a physical brick and mortar business, ultimately word of mouth, however it travels via email or you know, some other way or just actual word of mouth, that’s like priceless, right?
Bill Macaitis: (04:32)
Yeah. You know, in the voice of the customer, it’s never been stronger. I mean, if anything, you know, my wife runs a small business. I just think that if anything now, small businesses have much more leverage and much more power. And, and I love it, the, this age of SAS where you can get kind of best of breed software tools, products, you know, we’re, we’re the, the little guy can actually come out and succeed and, and they’re taking advantage of, you know, more digital operations, you know, digital advertising, word of mouth. Um, but that voice of customer, it’s not like someone has a great experience with you and you know, like just tell three of their friends now they have these massive platforms to go out and tell other people and then the power of that recommendation is exponentially more powerful.
So Salesforce, tell us a little about that transition. How big was it, you know, how established was it? Did you get to kind of make it what it was or drive a lot of growth? Yeah, so
Bill Macaitis: (05:27)
Salesforce was a, a little further down the road there. That being said, you know, there, you know, we talk about the cloud has been kind of being ubiquitous now and you have all these different SAS providers and we’re used to just, you know, logging in and our web browser to all these different tools. But at the time Salesforce was really kind of the pioneer there. You know, back in the day, you literally, for all these business software, you’d have to download them onto your, onto your computer or your servers. You’d have, you know, literally those, those old CDs just to install it. They’d be version, you know, if you couldn’t upgrade or maybe it would break and there are all these problems right in, it was very expensive and you’d have these maintenance fees you’d have to pay just to keep using it. Um, it was a horrible experience.
Bill Macaitis: (06:08)
And so here Salesforce comes, it’s like, hey, you know, we’re gonna make, um, business software as easy as just logging into Amazon, right? You just log into a webpage and you can start using it. Uh, and that was radically different. And it was really hard at first cause a lot of people are like, wait, you want us to put our most valuable sales contact information or customer information into the ethos and it’s going to be shared on the same servers as all of our competitors. And if people were like, what? Um, it, and it took a little while to kind of get over that. But for me that was an incredible challenge. Right. And when Salesforce kind of called me, they were looking for someone that had a little bit more B to C DNA that could kind of help take them there, their marketing efforts into the 21st century and use a lot more advanced online marketing techniques and you know, to, to really build up a marketing, a solid marketing tech stack and, um, and help build that brand up.
Bill Macaitis: (06:55)
So, uh, for me it was amazing. You know, I loved working with Mark. He’s such an incredible person. He’s an incredible philanthropist. Um, you know, he’s done so much good for the city of San Francisco, but really just anybody that’s built a business, um, kind of that uses this whole SAS in the cloud model. You know, he was a huge reason that they, uh, you know, the general population kind of embraced that and moved it forward. So it was a, it was a great experience working with them.
Yeah. Salesforce was definitely a pioneer. I was actually working at Dell in 2006, 2007 timeframe when they were first considering Salesforce as an option instead of the in house solution we were using. So I remember, I remember that being an interesting concept and thinking how cool it was. Yeah. Dell was a big early customer, if I recall as well.
Bill Macaitis: (07:42)
So then you moved to Zendesk as a CMO. How did that opportunity come up? Yeah, so I had been with, I’ve been with Salesforce for about four years and you know, again, just kind of looking for new challenge and Zendesk kind of came along and they were pretty small at that point. They were maybe, you know, maybe about 60, 70 people. Um, didn’t have a marketing team, you know, I had the opportunity to kind of come in there and build it up from scratch. So, you know, I, I came in as COO and built everything from scratch. For me, that was what really attracted me to the role because I think, you know, if anyone that works in marketing, a lot of times you kinda come into a marketing team where they’re already doing a bunch of things and um, you know, sometimes it’s good, sometimes things work, sometimes they don’t work though.
Bill Macaitis: (08:25)
Right? And, and I want an opportunity to come in with a complete blank slate where we could build a really modern best of breed team. You know, from an organizational design standpoint, think about like, what are these cutting edge roles that we could hire out for from a marketing strategy standpoint. Think about how we can build a really scalable high velocity inbound engine. We, you know, we layered a lot of content marketing. We did a lot of early account based marketing, did a lot of um, advertising, um, online, offline and it was just incredible the chance to build that up. And so, you know, we, we built the company up, um, you know, took them through the IPO and, uh, it was fun. I learned a lot there. You know, it was, it was interesting cause I think in, in B2B, you know, come from B2C background, like you want to be different, you want to be noticed, you want to have a brand that stands out well, when you shift over to the B2B side, um, you know, there’s, there’s this tendency to go, well, we gotta be super conservative and everybody has to wear suits.
Bill Macaitis: (09:22)
And you know, anything on our website has to be like this corporate stock photo of, uh, you know, people around a board room. And, um, and, and we tried something different in Zendesk. I mean, we had this massive green Buddha saying, love your help desk. Right? You know, trying to create this inner, you know, feeling of calm and tranquility and Zen because, you know, if you’re already in customer support, I’ve been in customer support and I’m sure people, maybe there’s some people listening to this podcast within customers. Work is not easy. It is hard, right? You have people that are just pretty much yelling at you for eight hours a day. And you know, this idea of like this, you know, some beautifully simple software that helped, you know, just bring a little inner peace and Zen, um, was really compelling and it was fun and you know, in, in businesses loved it.
Bill Macaitis: (10:09)
It wasn’t like, Oh God, they’re, they’re not professional, right? Because, you know, they have this, you know, unique visual identity or whatever it was, but it was, um, something that was fun and that’s something that, you know, like today what I do is I just do advising to other startups and companies and that’s one thing I always tell them, especially like SMBs is, you know, Hey, don’t be afraid to be a little different. Don’t be afraid to stand out, whether it’s your, your visual identity, your color scheme, your editor or tone and voice. Um, you know, that stuff that you know, you don’t need a massive marketing budget for, right? If you’re kind of in this, you know, boring, sterile, bland voice, you’re just going to sound like, you know, 90% of your competitors. And if, but if you can kind of stand out a little bit, that’s an awesome opportunity to someone to have a good experience with you, um, and really help you stand out and help you grow faster.
Bill Macaitis: (10:58)
So that was one of the tactics we use there that I think was, you know, that helped us out a lot and helped us grow fast. So, you know, at Salesforce and Zendesk and, and even, you know, kind of moving on, when I went to Slack, you know, we, we used advertising as a huge part of our growth strategy. Yeah. And so tell us more about that. Did the Slack just come to you and say, Hey, you know, it’s time to come over here? Yeah, I had, you know, I, so we, I’d gone through this endless IPO and Slack had reached out, you know, I think it was actually one of the, the VCs had, um, that invested in psych and reached out to me and really similar situation. Again, just, um, they didn’t have any marketing team at all. You know, they wanted someone to come in to build that function up, make it best in parade.
Bill Macaitis: (11:39)
And at the time it was really interesting because, you know, I saw my personal life that I was using messaging services more and more and more. Right. And actually if you look at the stats today, there are more people that use messaging services and even social. So there’s more people on, you know, Facebook messenger and what’s happened. Um, if kind of all of these messaging services and I’m like, you know, to me it felt like this trend is going to come to the business side as well. It’s just, you know, using messaging is inherently, it’s just some better system than email. Email was like, it just made 40 years ago was never made for team communication. And, and I’d say anyone that’s been on that one corporate email thread that just will not die. Why? All too, it just knows how, how crappy email is.
Bill Macaitis: (12:22)
So, um, anyways, I was excited to join them, but you know, at the same time Slack was new. But God, there’s been 20 years of collaboration tools out there and no one’s really been able to kind of break out. Um, and so for me, that was a fun opportunity to see like, could we create this, you know, kind of iconic brand, create a new category, um, leverage all of the learnings that I took the best to like the B to C side, the B2B side, um, and you know, the growth hacking, the inbound marketing, the outbound building, the brand, the personality to just make something special. Um, and, and it was an incredible opportunity and I got to build out the marketing team. Um, over time I actually took on more of a CRO role type role, so I let sales and success and the customer support teams as well. Um, but it was just an incredible experience. And, uh, you know, I loved being a part of that.
That’s awesome. And not many people have been, you know, a part of three back, well really more than three. But in this case, you know, we’re talking about three of the most recognized, you know, hypergrowth startups in the last, you know, 15 years, you’ve got Salesforce end desk Slack, and uh, you know, I’m wondering, so can you just give us some examples of some of the cool things you did and maybe even some examples of some things you’ve tried but backfired?
Bill Macaitis: (13:39)
Yeah, sure. So I think one of the fun things we did at Slack was we wanted to really look at reinventing a pricing and packaging. So it sounds kind of like a dull topic, right? Like pricing and packaging. But in the B to B space, there had been a lot of innovation around there. And so one of the things like we tried there that worked really well was we basically is opposed to a free trial, um, which most B to B businesses have, but they’re usually, they’re time-bound or user bound, right? So you can just try it out for the first two weeks or you can only have up to three users here. We said, you know, what, if we actually made a true free plan, right? And you could use it for a thousand people and you could use it forever, right? It was, it wasn’t like it was a very limited version of it.
Bill Macaitis: (14:23)
Um, we, we, we tried that out and that worked incredibly well. The idea was, um, you know, for in, especially SMBs, lettuce, SMBs, you know, they’re price sensitive. I get it, right? Like I, I’ve been, I’ve worked for SMBs, I’ve been part of SMBs. Um, sometimes you always have money for the tool, but you know, at the same time, there’s just a lot of SMEs out there and aggregate. And so when people are using your software, they’re there talking about it, right? And they’re, they’re telling their friends and they’re telling colleagues and, and then also people move jobs, right? I worked for an SMB. I’ve also worked for very large enterprises. And so you tend to take the tools that you really love with you and bring them into your organization. So for us, we looked at like, how did these free plans and these free users as these were incredible, you know, marketing evangelists for us.
Bill Macaitis: (15:08)
And they were going to help spread the word about what Slack is and what messaging is and how it can make your company more efficient and more productive. Um, and that was really helpful. Another thing we tried on the pricing and packaging was we had this, this concept, especially for small, medium sized businesses again, that, um, we’re, we’re, you’re busy. You’re only getting a build if someone’s actually using the product and if, and if they stop using it, we’re going to give you credits and refunds back. You know, that was very different. Even, you know, most other SAS products, even if you sign up for a year, you kind of have to pay for the whole year. But we had this concept of, Hey, if you stop using, if any user step using the product for like 10 days, we were going to give a credit back for that user.
Bill Macaitis: (15:47)
And so a lot of times these, these admins, whoever created this Slack accounts for their company, we’d get an email saying, Hey, Sally, stop using the product. Um, you know, we just gave you a credit back. And, and, and there was, they were floored, right? Yeah. They’re like, what? You’re actually helping us out. You’re giving. And a lot of times, by the way, so they just want a vacation for two weeks, you know, bless her heart. She didn’t log in good for her. Um, but you know, it just, it bought us a lot of Goodwill. And also I think it really centered the company around this idea that, um, look, we don’t get paid as a company unless people actually use our product. And so we had a big metric at Slack was, uh, a DAU are daily active users. It wasn’t how many people actually signed up for our service.
Bill Macaitis: (16:28)
It was just how many burned literally, you know, going in some products and using it every day. Um, and I thought that really just aligned us around this idea of customer centricity. You know, we want to have people with good experience when people actually use the product because a lot of people sell software and no one ends up using it. Right. Um, so that was really successful. Some things that bombed. Oh my God. I mean, there’s always countless, right. Um, because I’m always, you know, you always wanna try new things and some things work, some things don’t. So I’ll tell you a funny story. We, uh, this is what you’re doing, like an outbound campaign, right? And, you know, I was with Stuart and we found this really fun old 1930 song. I don’t think anyone had heard the song in like the last 30 years that had never been played.
Bill Macaitis: (17:10)
Right. It was still obscure, but were like, Oh, that’s such a great song. And we could, you know, we’re, we’re kind of imagining like, we can make a really cool commercial with this and, you know, it’s sort of like a great, you know, he’s like, well, all right bill, we’ll get out, we’ll go out there and find it. You know, I’m like, okay, so, you know, we reach out and, you know, we’re, you know, looking online like, well, who owns the rights to the song? Right? Cause I mean, it’s really obscure song. And we finally find, you know, the, the person or the company and we reach out and we’re like, Hey, you know, um, we’d love to use this for our upcoming campaign and, you know, we’re going to do a little video. And we think we were perfect for it. Like, Oh, that’s great.
Bill Macaitis: (17:46)
You know, and they’re like, well, who are you with? And like, Oh, well, you know, I’m with Slack. You know, I’m the CMO and I can literally hear them like typing the, you know, Slack in. And I’m sure they’re, they’re seeing these news, like select just received 100 million in VC funding. It’s all like, so, you know, how much would this cost? And they’re like, Oh, um, well, I think that’d be about $5 million. And almost like, what this song has not been played in the last 30 years. Like, how was, but anyways, the lesson I learned is, you know, when you go out and you’re trying to get rights for songs, you never disclose who you are. You know, you need to go through a blind intermediary. Um, but that was a good lesson, you know, that was a little scar tissue that I learned and hopefully it will avoid someone else from having to go through that.
Yeah. So, so the smaller you are, the more likely it is that you’ll actually benefit from telling who you are.
Bill Macaitis: (18:36)
Yes. Another great thing for SMBs out there, right? You can, uh, you can get these songs on the cheap, if you will.
So that’s funny. So if you were one of our builders, let’s say you have a smart team, you know, you have between two and 10 people and you know, maybe someone’s kind of dedicated to marketing, but you certainly don’t have a big marketing team. What are the top, you know, two to four things that you think people should be focusing on from a marketing perspective?
Bill Macaitis: (19:05)
Yeah, so like I said, I’ve been there, right? You know, small marketing teams, you know, not a lot of, not a lot of budget of, uh, uh, big ambitions and you want to help grow the team. So, you know, the, the couple of key roles that I look at, or at least when I’m kind of building out that team, you know, the first, um, thing I look at is like building out just the marketing ops side. So this is the person that just helps you build all the infrastructure, you know, marketing you, marketing basically spending dollar on people’s times, you gotta know if it works, right? So it’s the person, like we talked about those metrics early, right? That can help you measure aided recall on any recall. It’s the person that’s gonna build in your marketing automation, your web analytics, um, you know, your multivariate testing.
Bill Macaitis: (19:43)
Um, you know, all these tools allow you to be, act like you’re a marketing team of 50, even if you’re only a team of, you know, two or three people, right? Because these, these tools help you scale and grow. So I like, I like making investment. They’re like in someone that can handle the marketing ops. Um, I think product marketing is really important. So for me, that’s the person that’s gonna help tell the story of who you are. They’re going to think about the pricing and packaging. If you have a sales team, they’re going to help the sales enablement side. I think that’s really big. Um, I like, uh, content marketing. So you’re thinking about inbound, you know, writing content and helping that rank in SEO and delivering a lot inbound. Um, and then the fourth I think is like, you know, campaigns are an advertising manager or performance marketing manager, whatever you call it, right?
Bill Macaitis: (20:29)
Like that’s where you gotta get the word out. You know, I, I love word of mouth, but sometimes people don’t know about you and you gotta get the word out so they have a great experience and then start recommending you. So, um, I think that’s really important. And that’s, I think the great thing about today’s landscape is that you can have one person and they, the power to run, you know, these pretty sophisticated campaigns now. And I mean, it’s one of the reasons that, you know, I, I love what you guys offer. It’s like, Hey, you’re, you’re, it’s just like Salesforce, like Salesforce, democratize access to sales automation software and make any small business that can do it right. Um, and like companies like Marquetto were able, or HubSpot were able to democratize the press and be like, you’re democratizing this incredible access to all of these offline billboards, anywhere that you can have access to that you can, you know, upload it. It get your image out there. Just anybody can do it right? And you can start driving business. And I think that’s, um, incredibly powerful. And that’s, you know, I think that’s one of the most key roles in the team is, you know, that person that’s going to help their and set up these relationships, they’re going to help upload the creative, they’re going to help see the business grow. Um, and you know, for me, like as an SMB, that that’s gotta be a, a key part of your, your marketing mix
bill when it comes to, you know, your journey is such a fun journey to kind of, um, you know, hear about from you today. You were at Slack, you’re a CMO and now you are advising startups. Tell us about that move and, and kind of what you were going for and, and how it’s been.
Bill Macaitis: (22:05)
Yeah, it was E so I, you know, this was in the, I’m sorry, it was Slack for about three years and it kind of built up all the core functions, built the marketing and the sales success and support. And you know, I ended a point where actually I’ve been doing in a marketing leadership roles for about 20 years. Um, I’ve been really fortunate. I’ve had about five or six exits, you know, when you add up kind of the B to C and the B2B side. And I just was looking for another challenge. Um, and so I was either going to go down the, uh, the venture capitalists route, you know, or kind of just more an advisor route, you know, and, um, I liked the advisor side because you get to S, you know, really spend 100% of your time with these, you know, younger companies and help them with their go to market or their organizational design or their price, your packaging or the marketing tech stack.
Bill Macaitis: (22:50)
Um, and, and, and that just really appealed to me, right? Like, you know, I’m, I’m way too young to retire and I’m really bad at golf, so I love, I love working with great founders and helping them grow businesses. And it just, it was a really fun way for me to kind of pivot into something new. Um, and so that’s what I do now, right? I just, I work with other startups out there that are usually a, generally they’ve achieved product market fit, right? They have something that, you know, that’s got some traction and now they want to think about, you know, how do we pour some fuel on this fire and make it grow faster. And, um, and, and I just get a lot of reward out of that. I love working with good people, you know, and, and that, uh, you know, willing to embrace, you know, more modern growth strategies, um, but do it in a customer centric way. And, um, it’s something I love with, you know, work with a small select group of companies, but it’s something that I love getting out of bed every day and thinking about how it can help them out and, um, you know, just, just really enjoy this next, next stage of my, uh, my journey.
Awesome. So last question for you. What do you think, you know, based on your experience with these startups, what’s the most common mistake you see them making and where’s kind of the lowest hanging fruit for you to come in and redirect them to, to, you know, be more effective or to grow faster? Like, what’s that big? Is there one big thing, you know?
Bill Macaitis: (24:03)
Oh, there’s definitely one. Yeah, there’s many. Right? And by the way, it’s nothing wrong with it, right? Like I, I made lots of mistakes. Every startups making mistakes often. Right, right. It’s okay. That’s, that’s part of it. Um, the one I’ll say though, and this is just from my experience is most of the founders I work with, um, usually will come in and either say two things either say as part of their marketing, like, Hey, we need to work with a, we need to find a great PR firm or the PR firm we’re working with isn’t any good and we can’t get any coverage. And my hard thing is, you know, there’s like 10,000 startups out there, right. And that’s just kind of in like the text world, right? If you expand that out, there’s a gazillion, right? Yeah. And, and most of the tech founders I work with, bless their hearts, they all think that they should be in the wall street journal, you know, front page and that, you know, they should be the time person of the year.
Bill Macaitis: (24:54)
And it really like in, in, in PR. And my wife worked in high tech PR, so I got to know the space really well. Um, you know, 5% of the companies get 95% of the coverage. Right. Like, if you, if you read any kind of tech site, you know, it’s like Amazon, Apple, you know, Microsoft, Facebook, Twitter, they get like almost all the coverage and then that 5% that’s left to split up between 10,000 companies. So, you know, and it’s expensive. You’re talking about a 10, 20, 30,000 monthly retainer depending on the company you’re working with. So I usually say like, Hey, maybe pump the brakes, you know, on, on the PR. Um, yeah, unless you’re just this incredibly extroverted CEO that loves spending time talking with press and you’ve got this crazy life story and you’ve already hit three times and so the press knows you. Like, unless you have all that, like PR is just a really hard motion to get a lot of ROI on. And so that, that’s usually one that I, I say like, Hey, that’s nice, but maybe we can think about using those funds in a different place and we can get a bigger bang for our buck.
Interesting. Uh, that’s a, that’s good to know. Um, and I’ve had actually that same experience. I tried out PR for one of my side hustles for awhile and it was expensive and I was hoping for more than I got and I tried it out for a good long time to give him a chance anyway, so that’s good advice. All right bill, really appreciate you coming on today.
Bill Macaitis: (26:22)
A bar. It was a pleasure. Thanks again for having me. I’ve really enjoyed this.
Yeah, absolutely. Hey, builders. Um, go visit built to stay. Com common download. We’re going to summarize and put together a little review of marketing strategies that a bill has discussed on this episode and we’re going to include some tips on how you can implement them in your business. Also we’ll have the show notes and links, um, to Bill’s work that we discussed. All of that is on built to stay.com, so go check it out
next week on bill to stay over and over, over 24, seven or we could like at two in the morning, it’s three more people and then fall asleep. But then we could begin tweet more people, and we’d all do this for a couple of months until eventually it started doing it on its own. And people would tell each other when they had this problem, other people would want to come in and say, Oh, do use InstaSize. So that was the initial, what we call it, Twitter hack, what we did back in 2012 and read and review, built to stay wherever you listen to your podcasts. [inaudible].