Rajiv Parikh: 0:05

Welcome to the Spark of Ages podcast. Today we're sitting down with Bill Macaitis, a true legend in the SaaS world, who's been a marketing mastermind behind some of the most explosive growth stories in tech history. Bill's resume reads like a greatest hits album of hyper growth companies. He was the CMO and CRO at Slack, helping turn it into one of the fastest growing business applications ever. Before that, he was the CMO at Zendesk, guiding him through their IPO, and Bill served as SVP of marketing at Salesforce. We're talking about a guy who's been involved in five highly successful tech exits. That's not luck, that's pure skill.

Rajiv Parikh: 0:44

These days, bill is just not resting on his laurels. He's a growth and marketing advisor for AI and SaaS companies and runs SaaS CMO Pro, where he shares his expertise with the next generation of marketing leaders. He's become the go-to guru for product-led growth, a PLG. Bill's core philosophy keep it beautifully simple and always put the customer at the center of everything you do. Before getting into tech, bill graduated from the Geis College of Business at the University of Illinois, Urbana-Champaign, where he graduated with honors and made the dean's list. Some of the key takeaways you can expect from this episode We'll talk about product-led growth as an enterprise strategy, the importance of a customer-centric approach and beautifully simple software, holistic marketing metrics beyond the funnel and, finally, the imperative of continuous learning and adaptation. Bill, welcome to the Spark of Ages.

Bill Macaitis: 1:39

Oh man, Thanks so much for having me. That was crazy. I think it's the first time I've ever been introduced with saying that, I made the Dean's list and I think it was like one semester I got straight A's. That was pretty much it in college. The rest it was a little up and down, but that was fun to bring that in there.

Rajiv Parikh: 1:52

Thanks so much, we had to find some nugget about you that people don't know about, and that's what we found.

Bill Macaitis: 1:57

My mom will be happy that that was published.

Rajiv Parikh: 1:59

Yes, this this is a podcast for your mom, good deal.

Bill Macaitis: 2:03

Thank you, sir.

Rajiv Parikh: 2:06

All right, let's start with one of the favorite things you like talking about, which is PLG, and you've said before that the PLG initiative is one of the hardest things you've ever done, which is interesting, since the three last companies that you talk about so much and that you've helped build success for are those types of companies. So what I'm interested in learning about here is the technical and organizational hurdles. So what are the most overlooked emotional or cultural challenges that leaders and teams face when trying to pivot an entire organization towards PLG? And then, how do you foster resilience during that incredibly profound shift?

Bill Macaitis: 2:39

Yeah, yeah, it's a tough motion, right. You know, we had a lot of success with it at Slack, zendesk, salesforce, and when I kind of wrapped up those tours of duty, I was like, what do I do next in life? And I was like, you know, become a VC? And I'm like, oh, there's a million of those. But at least when I was going through my operator journey there weren't as many advisors that could come in and help out. So that's what I do now with their go-to-market grow faster. And I say it's hard because for a lot of companies that have gone down the SOG path or sales-led growth path, pivoting to a PLG motion is very difficult. It's difficult on a number of levels. I think one is just even getting what product-led growth is right. Maybe we start there right.

Rajiv Parikh: 3:19

Yeah, yeah, that's great. That's actually a great way to go.

Bill Macaitis: 3:22

Yeah, because I think a lot of people there's just a lot of misinformation or people think different things, right? Like I worked with one company who was like hey, we've made a ton of progress on PLG, we have a trial, and I was like, okay, like that's great, that's like one element of it, but there's a lot to it. So like, philosophically, the about it is PLG is this idea that people are spending more and more of their time in the product itself. It's that simple, right. And then how do you infuse your marketing into the product, your sales instead of product, your support, your success into the product? Right, and that's where it gets, you know, a little more complicated, right, because now you're going down high velocity motions. You're doing things like product qualified leads. You know you have freemium models, different pricing and packaging. You're thinking about the adoption. You're thinking about how simple it is to use. You're thinking about things like net promoter score. How many people are actually using the product, like DAU. So it's a wide area and it's difficult because, especially if you've done the SOG path and especially if you're a couple series up there right, so if you're in series C, d, e, f, whatever it is right A lot of the culture is built around the traditional sales model, which is all right.

Bill Macaitis: 4:30

Let's do outbound, you know, let's bring in a lot of leads, let's hand them all off to sales and marketing will run away and you know, hopefully we'll hit our quarter. And like the PLG model, it's just so different, like there's totally different metrics. Like I said, there's things like DAUs, you know, product qualified leads, net promoter score very different than a traditional SLG company. You know, I think culturally, a lot of people worry about some of the key tenants of PLG, right. So freemium I'm a huge advocate of freemium, like you kind of did a nice intro with the Slack salesperson, this but before I did 15 years on the B2C side and I've done almost 30 years of online startups and every single one I've had a freemium model right. And so for me it's like oh yeah, of course you do. There's all these benefits, higher growth, and it's not.

Bill Macaitis: 5:21

But for a lot of people freemium is scary. It's like, oh, what does that impact my quota, you know? Oh, my God, like I can no longer sell there. They keep pushing me up market. There's just a lot of like fears around it and once you've already invested in a certain model, a sales and growth model. It's very hard to pivot. Now the new SaaS and AI startups like it's amazing like 73% of them have adopted POG, so like that is the dominant model coming out. But for a lot of companies that are pivoting to it, it's a tough one. And it's tough from just all the different elements you need to do. But just really culturally, like I found like that's the hardest thing. You really have to get, you know the board behind it, you have to get the C-suite behind it, the founders behind it, sales behind it, product marketing there's all these teams that really have to buy into it if it's going to be successful.

Rajiv Parikh: 6:06

Is this one of those things where you have to be more top-down led, where it's coming from senior management and then they have to create a separate group that goes off and does this, or have you found it? Sometimes it's bottom-up or it's engineers wanting to build something or it's a group of folks wanting to do something on their own? As part of this, when you're talking about it, you mentioned, like there's you know, series, you know CEF. Those companies are pretty far along and they've built a level of ARR and growth Otherwise it wouldn't be at that level. So for them it must be hard, because there's an ingrained culture, to shift to Earlier. I guess they're in more experimental mode and they're willing to try new things. What are some couple key points that you find that stick out for you on that?

Bill Macaitis: 6:52

So one to kind of answer your question, I probably worked with, you know, 30 plus different startups on either building PLG for the first time and doing it the right way, or pivoting to it. And I would say, you know, from a pattern recognition standpoint, I will say the ones that have the hardest times are the ones that are further, like I said, in the series C, d, e, f type size, but also the ones that just assign a tiger team to it, like that. That's the one that I find like has the hardest time. You know, I found one company they were struggling with their POG motion and I'm like walk me through, what have you done so far? And they're like well, we have one guy working on it. You know he's, he's remote, he's over here. We have another thousand people salespeople doing this. And I'm like, well, you know that's that's going to be tough too when you just have one person one speedboat and one tanker.

Rajiv Parikh: 7:35

Right, yeah, totally.

Bill Macaitis: 7:36

I do find, like the ones that have a lot of success from just a practical standpoint, is one, you know, starting to use PLG metrics.

Bill Macaitis: 7:42

We talked about that like PQL daily active users, product qualified leads, and that's a different model, right? So the old model was you would just someone come in, fill out a form and they go straight to sales. And the new model you get them straight into the product, you wait for some certain thresholds of product activity and then the sales goes in. Right, so it's a qualified and it's product. And so I found it's best to adopt some of those metrics and then best to really have this as a company-wide initiative. Right? Because really to make it successful, you have to have product focusing on it, you have to have marketing focusing on it, you have to have sales focusing on it Right?

Rajiv Parikh: 8:15

I think you've talked about this in some of your videos. You just can't take your existing product and say oh you know, go play with it Right, cause usually most enterprise level products have training associated you have customer success associated, yeah, a whole onboarding process, and now you're basically saying put it in the damn product.

Bill Macaitis: 8:32

I'll put it another way. Most enterprise products suck. They're really hard to use.

Rajiv Parikh: 8:37

I got to tell you from my experience, when we've when we've tried to do it internally, where we've taken our tools and we've started with an enterprise product. I have a pretty good size marketing team that does the work. If the interface sucks, they just won't use it Totally.

Bill Macaitis: 8:52

Right.

Rajiv Parikh: 8:53

I can't force them, like other companies that have big operational teams. They just won't use it. They'll just find other ways around it.

Bill Macaitis: 8:58

Yeah, and that's a huge, huge part of a POG motion too, and why some of these later companies have a hard time pivoting into it is that typical enterprise sales motion is all about features. I need this feature, this feature, this feature, this feature, big feature, rack of things. Totally right, we look great on our checklist right.

Rajiv Parikh: 9:13

So what if the feature sucks?

Bill Macaitis: 9:15

Yeah, and the more features you add, the harder it is to use, right? So you know you have this really hard to use product and a big part of a POG motion is making it simple and easy to use, right. So I advocate for things like hey, after someone onboarded with you, give them a little like, hey, how easy was it to use a thumbs up, thumbs down? Right, yeah, if you have 17% thumbs up, ok, our quarter next goal is to get that up to 30% and then the 40%, whatever. It is Right but Right. But a very different model like product is used to building features and a POG motion. You're trying to make it simple, easy to use.

Rajiv Parikh: 9:46

So one of the things you have to do is you have to instrument the product.

Bill Macaitis: 9:48

Absolutely.

Rajiv Parikh: 9:57

So if you're not in the product itself like you're talking about, having those thumbs up, thumbs down capabilities in the product, which is not an enterprise thing If you don't have, then you're just not. And then, off of that, if you're doing it well, you're actually kicking off campaigns and notifications to totally other insights.

Bill Macaitis: 10:07

Teams are working cross-functionally. So a lot of times, too, like this isn't just product right Like a lot of time at Slack, the marketing team spent a ton of time in the product right and you know, what we would do is we would rewrite all the back end developer dialogue and prompts that they wrote and make it more fun and easy to understand. We would put in Easter eggs. We would, you know, religiously go through the onboarding flow, the signup flow for a lot of enterprise companies, like the signup feature, like was built like 11 years ago, right, and none of the execs have gone through the signup process in a decade, right, and they just they don't know, like, and they don't realize, like how hard it is to learn this totally new UI and taxonomy. And I think ultimately, like you know, kind of getting down to the brass tacks. It's like having these teams work together, you know, having it be a company-wide initiative, having the right metrics, having an advisor or just someone who's done it, you know that can come in and help them with that.

Rajiv Parikh: 10:58

So how do you make that flip happen? Because now you're saying the entire company has to work on this together. A lot of times your product designers are probably not the right people, or they need or they have to be open to help from someone that knows this way of doing this, this more Duolingo style or entertainment style way of using a product.

Bill Macaitis: 11:15

Yeah, b2c style right.

Rajiv Parikh: 11:16

Yeah, how do you think about that when you're coming in in that situation? Is this a senior level person, you know, getting crap from the the board saying this is something you got to look at, or they've gone to some events, that they've seen some things and said, wow, compared to these firms, I'm falling behind. Or is it something more organic than that?

Bill Macaitis: 11:34

Yeah, I think the impetus usually comes from the board. Right, the board is like saying, hey, if we want to go IPO, we need this level of capital efficiency, this level of growth. We're not there. We think PLG can help accelerate that, or even just more capital efficient. Right Like I work with some orgs and it's like my God they're using like human salespeople to sell to $5,000 and less ASPs. Right, and it's like the unit economics are just so hard to make that model work. Right Like you need a high velocity of that. So usually pressure from the board comes in. I think the CEO or the founders then, you know, want to try to move something like this. Right, so sometimes I'll bring an advisor like myself. But even the DNA of the company, though. Right Like I'm a big fan of like hey, hire some B2C people. Right, cause, like they kind of live and die by that. Like you can't have a consumer app that's super hard to use. There is no model where you can have 10,000 customer success people training every single person to use your app.

Rajiv Parikh: 12:29

Right, it just doesn't work, right yeah.

Bill Macaitis: 12:31

Or even, like you know, it was funny like Stuart and I from Slack he was the founder there we both had a gaming background Right, and so we kind of understood, like in these, even these enterprise was originally going to be a gaming. It was going to be a game, right.

Rajiv Parikh: 12:44

He comes from blogger right, which is a very much very much of a consumer blogger flicker consumer.

Bill Macaitis: 12:50

And so we we spent a lot of time making, you know, slack fun to use, right, because if it's fun, people use it. So we spent a lot of time on like hey, like our most successful integration you'd find this hilarious. It wasn't like HubSpot or Marketo or Salesforce, it was Giphy, like everyone wanted to use, like the automated Giphy. We had a message loading of the day. You know we had an emoji support. That was huge, you know. It was like all these fun things that matters, right. If your product is like just painful to use, it's not fun at all, of course people aren't going to use it, they're not going to recommend it, they're not going to talk about it. So like it's a very different playbook. And that's just why I say like it's a little bit hard, right, like if you're going to, you know, go down that path.

Rajiv Parikh: 13:33

You're saying, when you're going to do this, you better really commit. Yeah, and you have to align the team, you have to change your metrics and how this works, and I'll tell you. Here's something interesting how did I get my company to move off of emails and other chat applications to Slack? I couldn't get people to move.

Bill Macaitis: 13:51

Oh, it's hard.

Rajiv Parikh: 13:57

CEO of a couple hundred person company should be able to get shit done. So no, what we did was in one of our larger offices every day we have a snack in the evenings that people go to the cafeteria to eat, and we found that that worked better than giving out free lunch, free dinner, because everybody had such weird diets. So I said we are not going to send out another email about this. You're going to put this on Slack.

Rajiv Parikh: 14:18

And so they every day would publish that on Slack. And then the other thing they did was for birthdays. They created a celebration channel and then you get celebrated on your birthday. So that drove adoption more than company-wide announcements. Team-based, client-based initiatives that's what worked.

Bill Macaitis: 14:37

Isn't that funny. Yeah, it's the little things and I mean you hit it on the head right, like half the stuff with PLG or really any new initiative, right, like AI is a huge one. How would you embed AI in the company? It's more of a change management exercise. I found it's less hard figuring out, like what do you do with PLG and the steps. It's a little difficult, but hey, I can lay it out pretty easily. Like what's more challenges like how do you transform a 300 person organization, a 5,000 to 10,000 person organization, to really like buying in and understanding, like how this can still help out your growth rates and be more capital efficient.

Rajiv Parikh: 15:08

So you totally. You led me right to my next question, which is all about AI, right? So you're obviously a fan of AI, I'm sure you're using it even as part of your advisory service.

Bill Macaitis: 15:17

Yeah, absolutely.

Rajiv Parikh: 15:18

Doing all these amazing content pieces that you're doing, and you've talked about PLG landmines. So what are PLG landmines like? Poor onboarding, lack of product stickiness, internal misalignment that AI, in its current and near future state, is uniquely positioned to solve or significantly mitigate, perhaps in ways that traditional methods don't or cannot.

Bill Macaitis: 15:38

AI is transforming every single element of businesses right now and I am a full fan of it, right, and I think it's incredibly powerful. There's still a lot of hiccups now that anyone will see it'll hallucinate or just maybe not go down the right path, and you know part of choosing the right model and the right base LLM but I do think it's going to help every area right. Including PLG like a huge thing that allows now is more different pricing models, right. So I mentioned I'm a huge fan of freemium. A big model that is becoming much more common now is outcome-based pricing right, and that's being kind of enabled by AI in a PLG model to where you basically say, hey, we're all getting in charge on a successful outcome for your business, right. So if you're in customer support, for instance, historically it was oh you'd pay for you know per seat how many you know customer support agents you had, or maybe it's just some giant licensing fee and you can't do that as much anymore if you have a whole bunch of non-human agents.

Bill Macaitis: 16:33

Non-human agents right, so it forced like we had to evolve, right. And so now you're seeing, hey, it's being priced per successful resolution right so Intercom Salesforce resolution right so Intercom Salesforce a bunch of the pure AI companies are adopting towards that. I think that's a really cool thing. I think another cool thing that AI is enabling is personalization at scale. In the past it was just impossible to provide the level of personalization and that could be on the outreach side, that could be on the onboarding side, that could be within the product itself. But AI is enabling huge amounts of advancements there the targeting, the content, the video, just every single element. Right, Like. It's hard for me, as a former CMO, to think of any individual team I had that is not being, you know, completely changed in how they do their work. That's right, and the power of it. So, yeah, I'm a huge fan and I think this, you know, movement is here to stay.

Rajiv Parikh: 17:20

So, yeah, so like you, I sat with some of one of my clients. It's a pretty good size. I think it's like series E or F1 integration firm who will be nameless. Amazing people have. Some of them have been on the show and they. That was the number one topic of conversation when we were talking about AI and agentic AI is what do I do with the pricing model? It's a huge issue and even outcome is hard. We're trying to do this with us, which is we have outcome for our services right In a sense, like I deliver a website or I deliver this content or I deliver certain results for the campaigns that I run, but some things are by the hour and I think AI gives us the opportunity to actually charge based on an outcome and a successful outcome and finding that well and verifying it, and there's a lot of opportunity there and I love your point about personalization. I mean this, I think, is the greatest opportunity for marketers to truly go to one-to-one marketing.

Bill Macaitis: 18:18

Absolutely.

Rajiv Parikh: 18:19

Marketing and sales in many ways merge, because a lot of times the marketer creates the strategy and creates the headline and the thrust of what they're supposed to do, and then sales executes it.

Bill Macaitis: 18:30

But if I have, a bunch of agents doing it. Yeah, yeah, there's a lot of like, what's going to happen, right, like I've always thought kind of philosophically like marketing is just kind of automated sales. Yeah, you know, we build these campaigns, we're doing a lot of, you know, advertising, messaging, high velocity type stuff. But I mean it's going to be fascinating, right Like.

Bill Macaitis: 18:46

I think the pessimist in me is like, oh my God, like every single job in white collar land is like going away, except for maybe some generalists that know how to run all this stuff together. The optimist in me because I have a daughter and I want her to grow up in a, you know, a good world is that, like man, the barriers to entry to creating new businesses are just tumbling down and you know she will have access to you know, hey, she's not a legal expert Great, she's got a legal agent, right. Or she's got a sales agent or a marketing agent or hr, all these ones. And not only that, the prices are coming way down, right, with all this new competition, yeah, um, and the iting more efficiently. So I'm hoping that it spurs a whole bunch of new businesses and new landscape.

Rajiv Parikh: 19:27

But I know, every time a new technology comes, it's always scary, right everybody's always scared, but they were scared during the internet, right when the internet first came out like everything changed I think it's this thing where we can't envision the unknown and we have to just trust economics and trust that people have to buy things. Robots can buy things, but robots can't.

Bill Macaitis: 19:47

Yeah, they can't go on vacation. Not everyone has $10,000 to work with a lawyer, right, or can hire expensive sales. I think it's a good thing overall.

Rajiv Parikh: 19:59

I know we're going a little bit away from marketing, but when my son was graduating from law school, his dean of the law school said one of the things AI. There's a concern that we'll get rid of lawyers, but actually legal filings will be easier to do for folks that don't have easy access to lawyers, so now they can actually get, they can redress their grievances through the legal system in a way that they couldn't. So maybe AI can help change things for the better in ways that we just haven't thought of.

Bill Macaitis: 20:25

Yeah, democratize it Definitely.

Rajiv Parikh: 20:27

Okay, so going a little bit away from AI, but kind of staying with it. This is a hot topic among CMOs. Right that a lot of them have objectives where they have to source leads. Right, or even source MQLs. You know John Miller really well.

Rajiv Parikh: 20:42

He'll go crazy over that right. He's like I created. You know, with Marketo I created this machine where marketers turn into MQL generators, when really marketers are supposed to be much more about building a market right and much more about driving the overall system, working hand in hand with sales. So in a PLG world, are there specific product-led features or experiences that help marketers and sales work more effectively together? How do they integrate in this?

Bill Macaitis: 21:11

Yeah, yeah, it's a great question, right, and I know, john. Well, we just did a big B2B industry marketing benchmark survey and so we were. You know it was fun to kind of publishing that. But yeah, I think, ultimately, like you know, these teams can and should work together. I think, like, fundamentally, like how B2B splits up marketing and sales is just based off like a 30 year old relic go to market model that's gotten really old and dusty and it hasn't been updated. And, look, I think marketers should be focusing in every single stage of the journey, right From prospect to lead to opportunity, to close business, to expansion, to going in new product lines, right, like every single element of that marketing could be in there helping out, right, and also sales, too, right. Like I think they have a part of that journey. These teams need to work together.

Bill Macaitis: 22:03

I think the PLG model is a much more efficient model, right, so we talked about that earlier. Like this old model where you come in as a visitor, you just see some form that you want to access piece of content. You fill out the form. All of a sudden sales starts calling you way too early. You're not ready. It's a bad experience when the new model is like hey, you come in, create this tent, they land there, they go straight into the product. Maybe there's a freemium model, very low friction. They're experiencing value quickly. Now you have a concept of a product qualified lead. All right, it came from this company. We historically sell well into this vertical. They've passed this usage. Hey, now sales is going to reach out much easier sell. You know they're already using the product, they like it. You have some internal advocates already there. But you know that just means that these teams need to work a little bit differently and work together.

Rajiv Parikh: 22:49

Right. Are these metrics like shared metrics then?

Bill Macaitis: 22:51

I do, yeah, I'm I'm a big advocate and I think, john as well as like of having shared metrics Right. So I think when, when you create a model where marketing is just in charge of like leads and then sales in charge of the rest, it just creates friction.

Rajiv Parikh: 23:04

It's just warfare. It's open warfare between each other. Yeah.

Bill Macaitis: 23:07

Put them on the same goal. Now you could argue it's a funnel based goal and that's fine. I would argue, funnel based goal. So when I say funnel basedbased, I'm like leads pipe, closed business. Funnel-based goals, in my mind, encourage very short-term behavior. Right, we have to hit next week, we have to hit next month. It encourages you to lock everything down, use bad sales tactics, promise features that don't exist. Right, just do whatever you can to get the sale right. Like I think it's a little bit smarter to think more long range. So in the product like growth world you are thinking about daily active users, are people actually using the product? Do people actually like the product? You know? Are they past a certain threshold? But I also think, like, like brand stuff right. Like, hey, what is aided recall sentiments share voice.

Rajiv Parikh: 23:49

Right. So. So now you're, now you're getting into Brett, so these are soft PLG sorts of metrics, right so?

Rajiv Parikh: 23:55

so when I when I'm doing the PLG it's not just, it is daily active users, product qualified leads and, of course, I'm sure you would say this is for my ideal customer profile right, because sometimes PLG leads you to get a customer that you actually won't get revenue from. I'd love to hear your point of view on that, because I ran into that situation in my own company. But then takes you to the soft ones that you're talking about, like brand affinity. Or is it share of voice? Are we still in the share of voice? Aided unaided Are we still doing that?

Bill Macaitis: 24:26

You know there's a whole host of brand metrics out there. I would just say this A lot of companies that I've worked with on the B2B side are tracking zero brand metrics. Yeah, right, and I just think that coming from the consumer side, like hey brand, is kind of a long term leading indicator. Right Again, if you only focus on short term demand gen, you're not building up any type of affinity, you're not building up awareness. A really common thing that startups will come to me is the founder will go like hey, I love our product. We've got like 15 customers, but no one knows about us product. We've got like 15 customers but no one knows about us.

Bill Macaitis: 24:59

Right, like you know and hey, that's that's kind of an issue of sometimes the metrics there.

Rajiv Parikh: 25:03

It's the hardest way to walk into, the hardest way to grow Like I mean, you got to go in and explain who the hell you are and and they're coming in skeptically and, as you know, Bill, like now in today's world, where people expect to interact with their product, their consumer products, they like to find you before they find them. I think what for?

Bill Macaitis: 25:16

exactly the last.

Rajiv Parikh: 25:16

Forrester event.

Bill Macaitis: 25:17

They're saying depending on whether you're a Gen X, millennial Gen Z, you're going between 60 and 80% of people who find you before you find them.

Bill Macaitis: 25:29

Oh, I've heard that even 80, 90%, you know, depending on the, you know the analysts putting that out there.

Bill Macaitis: 25:32

So, yeah, I mean this, the entire buying model has changed, right, and I think, at the end of the day, kind of understanding how these different models you know, product led growth, sales like growth there's also like product led sales which I like and that's I'm a big advocate of is like, hey, get them in, get them into the product, right, and obviously you have to do your homework, do the right ICP, do the right marketing, so you're bringing in the right people but then, like you know, you score it and then sales reaches out to them, right, but sales doesn't reach out to everyone because salespeople are very expensive and you want to only have them reach out to the right ones. Much shorter deal cycle. Now the, the people that don't buy. I'm actually like I have a pretty strong point of view on this. So I've done a couple of videos on SESCMO pro. By the way, if anyone wants to watch these videos, just go to CMO procom and you'll, you'll see all of them.

Rajiv Parikh: 26:16

I'm a big advocate. I love, I love what you've done. You've made it super easy for people to understand. You've done a great job with your YouTube shorts that then lead you to these somewhat longer and then much longer episodes, which are chock full of great information.

Bill Macaitis: 26:29

Thank you so much man, like I try to make them simple and fun, right. You know just anyone that can wants to learn about this stuff here. But anyway, like I'm a big, so I've done a really long video just on freemium because I'm super passionate about it. And the best way that I like to think about freemium and people coming in that maybe aren't willing to pay is that it kind of goes back to the earlier discussion with the POG and the board. Right, the board investors, wall Street, wants capital, efficient growth engines. Right, they want fast growing companies that have the right margins, that are profitable.

Bill Macaitis: 27:01

So you have this spectrum of how do you achieve this growth? Right, and there's some old school models which is like we're going to just do outbound sales. There's inbound sales, there's outbound marketing campaigns, there's inbound marketing, seo content and there's like PLG and word of mouth. Right, the more you go down that spectrum, the more capital efficient it gets. Now freemium is a really good example of it's kind of a mindset. So at Slack, we had millions of free users, right Like 10 million free users, and some people look at that and go, oh my God, I have 10 million people that I have to pay bandwidth for and support and there is a cost associated with everyone that's free users. I looked at it as like wow, my marketing team at Slack is 10 million.

Rajiv Parikh: 27:41

Like I have a 10 million strong marketing team, especially if they're using it, right yes, not just listed or signed up If they're actually using it. This is freaking amazing.

Bill Macaitis: 27:51

Yeah, absolutely Right. And so I always looked at it as like hey, because sometimes when you get the pricing and packaging, like, I never liked a free trial because it's basically saying, hey, we have all these free marketers, but at some point we fire them Right, you hit the 30 day trial, you can no longer use the product, you're all fired Right and in lieu of that. So if you don't have a freemium plan, what a lot of times will happen is it's like OK, marketing, we need you to go get 10 million DAUs. Okay, I can do that, I can run my YouTube ads, I can run my billboard ads, I can do all this. But hey, that costs some serious dollars. So let's compare those dollars versus the dollars of the bandwidth, the support costs for the free user, and usually it's significantly less.

Bill Macaitis: 28:30

So I like the freemium models for those that want to like dominate their category, like really win the awareness battle. That's huge battle for it. Also, what you'll find is like SMBs are historically super price sensitive. A lot of SMBs just aren't going to pay you regardless, but there's a ton of SMBs out there and they move jobs, they move to different companies, they have friends of different company sizes, right. So, like I always was on the model of like, have a freemium model, get the awareness benefits but then sell to the enterprise and that's where you make your money right On these higher plans.

Rajiv Parikh: 29:00

And then would you do that as part of your segmentation or your reporting, saying, okay, yes, I have 10 million and I know of this I'm going to get a much smaller amount that actually pay and a certain amount that. Then you know, we did this with a bunch of clients of ours and then a certain amount is going to be enterprise, and so you're presenting this model and then you're showing it with multiple lenses. One is just pure demand gen for enterprise, but the other one is brand awareness, their mobility to other places, their word of mouth association, maybe sales velocity. Right, you could probably do it that way.

Bill Macaitis: 29:33

Yeah, sales velocity, and also it does having a freem mail. On a weird way it opens up a lot of land and expand for enterprises Right. Like when we were at Slack, we would constantly have the scenarios where some teams like IBM and Southeast Asia, the design team, started using us Right and then it started to spread on the free plan, then it spread to another team, another team, another team Right, all on free plans and eventually like, oh well, we want to upgrade, we want to have one bill, we want to have consolidated reporting, we want to have SSO for all these teams right Admin settings. So then they come to you, then they come to us, right, or we would reach out to them too. Sometimes it could be either scenario there.

Rajiv Parikh: 30:08

So now we're talking about this with the disruption of AI. So you have this whole situation Like you talked about. I mean, chatgpt is a classic ChatGPT Cloud Gemini classic examples of pure freemium-based strategies where it's pretty expensive to generate an image. Right, I think we saw that thing about ChatGPT saying hey, maybe chill out on the what is it called Ghibli generation.

Bill Macaitis: 30:30

Studio Ghiblis.

Rajiv Parikh: 30:33

How should companies rethink their long-term go-to-market strategy? How should companies rethink their long-term go-to-market strategy so they're looking to build resilience, adaptability, relevance, where go-to-market functions may be completely redefined by AI, it's more than short-term gains. What does a future-proof go-to-market look like from your perspective.

Bill Macaitis: 30:50

I don't know if there's any future-proof go-to-market. I mean, I always try to look at it as like. For me, go to market is always evolving and improving and adapting and iterating. Right, like, if you're a CTO, you get fired. If you're like you know, we're just going to use the same coding language we did 20 years ago C++ that's great, we're going to use it everywhere. Right, they're like what? But a lot of times they go to market Literally you hire this person, they're like we, we're gonna use the same classic go-to-market model I've been using for the last 30 years. It works, damn it, it's outbound, right, I don't like, hey, I love product like growth, I love product like sales. I have freemium models. But it's always iterating, it's always evolving. And I will say you see companies that have adopted the right go-to-market model, like a cursor, for example, you know, on the dev side with ai, you know brilliant, 100 million and just like I.

Rajiv Parikh: 31:35

I didn't even know about cursor till I last visited my operations team and they're like, oh yeah, and before I was like, hey, how's that get github, uh, copilot. They're like, oh, we've already, we have that in cursor.

Bill Macaitis: 31:46

And totally here's the context by which you use either yeah, it's amazing high velocity freemium model. A lot of these startups, too. I just started working with another ai startup that you know. They're in the lean model, lean model. So they're like hey, they only have 13 people, 20 million ARR, right. So you really have to think about. Like, hey, how is what is the capital efficiency of these different models? And they do make a huge difference. Like the go-to-market model you choose has huge, huge implications. The pricing and packaging you use premium product, like growth, like there's all these different elements that can just really make it. And I think I'm a big believer. Like, hey, adopt the AI tools. Now, the pricing, the adoption, the personalization these are ones that are just going to give you force, function, improvements and essentially make that go to market. Just modern, best of breed, moving forward.

Rajiv Parikh: 32:29

Totally agree. It's like learn or die, right, get in or get wiped out. So I'm with you 100% on this. All right, bill, this was tremendous amount of insight. You've packed so much into a really short amount of time, so now it's time to really test your skills.

Rajiv Parikh: 32:44

We're going to go to the spark tank. So let me lay it out for you, Bill, Welcome to the spark tank where business legends face their ultimate test, and today we're putting decades of strategic thinking to the crucible. Today we're thrilled to have Bill Macedus join us, a man who's been studying business longer than most people have been alive and has the track record to prove that all that childhood fortune magazine reading actually paid off. Tonight we're putting all that accumulated business wisdom to the test with the ultimate pivot point challenge.

Bill Macaitis: 33:18

Wow Okay.

Rajiv Parikh: 33:18

We're going to drop you into the most crucial decision moments in business history, those make or break crossroads where companies either soar to legendary status or became a cautionary tale in a tough Harvard Business School case study. Here's how it works I'll describe a famous company at a crucial decision point, without naming them, and you'll need to identify the company and predict what they should do next. Then we'll reveal what actually happened, to see if your strategic instincts match up with business history. So, bill, are you ready to prove that your business pattern recognition is as legendary as your growth track record?

Bill Macaitis: 33:54

This is crazy. I've never done this, but let's do it, man, this sounds fun.

Rajiv Parikh: 33:59

All right. Well, that's why we had you here, bill, just to set you up for this. All right, here's scenario one You're running a scrappy software company when the most powerful name in business calls. They're secretly building their first personal computer and desperately in need of an operating system. The giant offers you a choice Sell them the operating system outright for immediate cash that would solve all your money problems or demand ongoing royalties for every machine sold. This hardware giant has never failed at anything, but personal computers are uncharted territory. What's your move? A sell the operating system for a large lump sum. B license the operating system for a royalty on each computer sold. C decline the deal and focus on your own hardware ambitions and this is if you're really thinking for. D open source your operating system to build a community and attract more partners.

Bill Macaitis: 34:53

All right. Well, if my history is right, I believe this is Steve Jobs and Apple being approached by Bill Gates from Microsoft, and I'm pretty sure they went C, which was a pretty gutsy decision at the time, but obviously played out well, with an integrated hardware and software offering.

Rajiv Parikh: 35:06

How about if I play a part of it back to you? And see if you change your answer. You're a scrappy software company when the most powerful name in business calls they're secretly building their first personal computer and desperately need of an operating system.

Bill Macaitis: 35:19

Is this Microsoft and IBM? Oh, my God, okay, and so they oh, I thought it was because you said it was a cool software system. So I thought it was the GUI that Apple had. Oh, I got you, I got you here, License right.

Rajiv Parikh: 35:32

Yeah, there you go.

Bill Macaitis: 35:33

Boom, and a deck of corn was born.

Rajiv Parikh: 35:36

Yeah, that's right and is just ridiculous today. So the company is Microsoft. Bill Gates, I think. He bought DR-DOS for $64,000, then said he had it. He with his good buddy Paul Allen then said he had it. He with his good buddy Paul Allen went out and they sold it to IBM and they had the IBM PC and he chose to license the OS to IBM MS-DOS to IBM rather than sell it outright. And it allowed Microsoft to license the OS to other PC makers as well. Ibm did not restrict them, even though they wanted to, fueling a meteoric rise and dominance in the software industry.

Bill Macaitis: 36:10

That's a good one, two fueling a meteoric rise and dominance in the software industry. That's a good one, yeah, okay.

Rajiv Parikh: 36:15

So Bill Gates and Paul Allen at the time, all right. So here's number two. This one's going to be a little harder. You're leading a tech startup that assigns three word addresses to every three square meters on earth. After launching in three countries, the results are mixed. In Mongolia, nomads find it useful, but don't pay. In Germany, automakers license it for their navigation systems, but growth is slow. In the UK, adoption is near zero, despite marketing aimed at consumers and businesses for vehicle breakdowns and accidents. With cash running low, you must choose a survival strategy A double down on Mongolia, refining the product for nomadic communities. B focus on Germany's auto industry, betting on luxury car partnerships. C pivot to emergency services in the UK, positioning it as a life-saving tool. Or. D abandon all markets and open source the technology.

Bill Macaitis: 37:03

I feel confident saying doubling down on the market in Mongolia. I don't think I've ever heard that in any Harvard business case success story, so I'm going to rule out that one. This has got to be around like geofencing or geotargeting or some tech there, so I'm guessing it's more on the. They probably went with the luxury automakers for maybe the mapping side of it. I'm guessing I don't really know who this is, but that'd be my best guess.

Rajiv Parikh: 37:29

I thought this was hard. I wouldn't have been able to guess this one that easily, so A. I think you're, I'm going to exclude A Willingness to pay is going to be-. We're going to double down on Mongolia. Sorry if anyone's from Mongolia here, right?

Bill Macaitis: 37:43

now, but you just don't normally have that listed in the top software market.

Rajiv Parikh: 37:46

The future Genghis Khan is there, right. So the future Genghis Khan is there, right. So there you go. And then, so let's choose between B and C. So focus on Germany's auto industry, betting on luxury car partnerships. Pivot to emergency services in the UK, positioning it as a life-saving tool.

Bill Macaitis: 37:59

All right, I could see C too. I mean, I was torn between B and C here.

Rajiv Parikh: 38:02

And I'm not going to expect you to know the company, because that was hard, I didn't even know it. But but I will say the answer is the company's called What3Words. So What3Words is a proprietary geocode system designed to identify any location on the surface of the earth with a resolution of approximately three meters. It is owned by What3Words Limited, based in London, england. The system encodes geographic coordinates into three permanently fixed dictionary words, and they chose… London, I'm assuming, and they chose London.

Rajiv Parikh: 38:28

I'm assuming, targeting emergency services. A national TV campaign showcasing how the system saved lives led to adoption by police, ambulance services and outdoor rescue teams Makes sense. That's a pretty cool solution. This pivot transformed them into a critical infrastructure tool, which you could argue. I think it's a fair argument to say go after automakers, because that's a long-term way of being successful or something immediate which is emergency services, but now you're going after government which is also hard.

Bill Macaitis: 38:52

So this was a tough one. We talked about tiny spec, which was Slack the game, before it pivoted to a business messaging platform. So sometimes pivots are the right way to go, yeah.

Rajiv Parikh: 39:04

Well, this is all about pivots, so here we go. Next one you're CEO of a hundred year old textile manufacturer. Sales are collapsing, factories are closing and bankruptcy looms. A disgruntled investor who owns 49% of shares proposes a radical plan Shut down textile operations immediately. Use remaining capital to acquire an insurance company. So search your mind for some history. This will, this will okay.

Rajiv Parikh: 39:32

Okay A accept the plan, betting on his investment acumen. B rejected and seek a government bailout for textiles. C counteroffer keep textiles running part-time while diversifying. D liquidate everything and distribute cash to shareholders.

Bill Macaitis: 39:48

Man, our listeners, nailing all these. I'm going to go this is a Berkshire Hathaway Warren Buffett thing and I'm going to go A that he knows his stuff. I could be wrong here. I actually think a fascinating parallel before you answer is really the cash cow dilemma that Google has right now. Right, are you just going to show the answers or are you going to continue to show links? Right, and they are caught in that classic innovators dilemma of what do they do, right? But anyways, all right, we'll go back here.

Rajiv Parikh: 40:16

I think you're right on with today's challenge and we should note that, because the choices they make today will dramatically impact their future. You're right. It's Berkshire Hathaway. There's a famous investor. His name is Warren Buffett, young guy at the time, chose A. He terminated textiles, acquired national indemnity insurance and transferred Berkshire into a holding company for investments like Geico, dairy Queen, so many others. The pivot created one of the most successful conglomerates in history.

Bill Macaitis: 40:46

He's got a pretty good track record.

Rajiv Parikh: 40:47

Yeah, he's pretty damn good, and he just recently stepped down at what 92 or 4 or something I know, I know Just incredible Still living in the same house.

Rajiv Parikh: 40:55

It's a crazy story, same house drives the same car, but does like to fly net jets because he owns it. So, all right, I have an interesting one for scenario four. Okay, yeah, you're leading a startup building encryption software for handheld devices, so this is another pivot. The dot-com boom is in full swing, but your core product is not gaining traction. Few customers are buying security software for devices. Meanwhile, you notice a surge in online auctions, especially on a new site where buyers and sellers struggle to exchange payments quickly and securely. Your team proposes a radical pivot Abandon handheld security and instead build a digital wallet to let people send money by email. This would mean a complete overhaul of your business model and a leap into the unknown world of online payments. Okay, what?

Bill Macaitis: 41:41

would you?

Rajiv Parikh: 41:41

do A stick to your core. Double down on handheld device security and wait for the mobile market to mature. B seek a merger with another struggling fintech startup to pool resources and survive. C license your encryption technology to bigger software firms and exit the consumer market. Or D pivot to digital payments, launching an email-based money transfer service for online buyers and sellers.

Bill Macaitis: 42:04

Well, I'm going to guess this is a D, this is PayPal. I could be wrong here, but that's the direction I'm going. First of all, you're talking about eBay here, or maybe we're going down the crypto path, but yeah, I could be wrong here, but that's the direction I'm going. First of all, you're talking about eBay here, or maybe we're going down the crypto path, but yeah, I'm going to go PayPal on this one.

Rajiv Parikh: 42:14

Totally nailed it, bill. So the company is PayPal, originally Confinity, founded by Max Levchin, peter Thiel and Luke Nosen.

Bill Macaitis: 42:22

Yeah, there's a mafia.

Rajiv Parikh: 42:23

There you go, and of course, we know Elon Musk eventually made his way into that with xcom. So they yes, they chose X. They pivoted digital payments, launched PayPal. A lot of people send money via email. There was a massive pain point, as you're talking about, for eBay users, right? Ebay eventually bought them. Paypal became the default payment platform for online auctions, leading to its IPO in 2002 and acquisition by eBay for $1.1 billion that same year.

Bill Macaitis: 42:46

Cool history.

Rajiv Parikh: 42:47

It's amazing. Fun game, yeah, fun game. So your point on Google? So this is a point where they make their money by providing links to others. They are providing to the consternation of many firms that are trying to get their SEO results. They have AI overviews at the top. They now push, they put their ads in between and they push organic results way to the bottom. That's their response to it. Or they could just like ChatGPT and OpenAI, just provide a damn good answer.

Bill Macaitis: 43:15

For me. I think they're missing the boat on this one. I know they're trying to transition softly, but I think that's really hurting their brand, because the problem is all the people that still go to Google and, by the way, I don't think they've rolled that out universally. I think they're doing it very geographic and segment wise. So a lot of people are still getting the same old frustrating experience and they're trying whether it's, you know, claw, chatgpt, perplexity and they're having a much better experience it's a 10x better experience and they're losing, I think, a lot of people. I mean, I just think they know the direction it's going. You just need to show the answer. You can still show the citations and there is, like you said, a whole AI optimization there.

Rajiv Parikh: 43:49

What do you do with hundreds of billions of dollars of revenue profit?

Bill Macaitis: 43:53

You know, you say, hey, we're focusing on the long run, right, like that's what founders are supposed to do is look beyond this three month, one year hurdle and look towards the long run. Look, I think ChatGPD has got a pretty good valuation right, and they're just showing the answer. Right, and they've evolved their business model to include subscriptions right, and they've evolved their business model to include subscriptions right, which is a natural evolution. There they're selling to enterprises.

Rajiv Parikh: 44:14

I even saw them the other day when I asked about traveling somewhere. There's like do you want us to book it for you? So just like. Google allows you to get commissions by sending you to a booking service. They're starting to do the same thing.

Bill Macaitis: 44:25

I feel like Google has like it's in parallel to our earlier conversations. They've used SLG for so long and it's been really successful and a new go-to-market model has come out. It's better, but they're kind of like just well, let's just put two people on this and dip our toes in and I get it. It is literally like the classic innovator's dilemma. This is like what Harvard Business Review everybody writes about, right, and there's a huge shareholder pressure not to let profits go down or revenue go down in the short run. But I just think anybody watching this like there will come a point very soon probably where you know Chet Chibiti is going to eclipse enterprise value of Google. Close behind them will be Anthropic and Perplexity. And it's just like anyone watching that follows the space knows it.

Bill Macaitis: 45:09

What about Gemini? I think Gem. Like anyone watching that is follows the space knows it. What about gemini? They have, I think, gemini. So the gemini is great, but they hide it like it's hard to get to. Like I want to just use it too. Like I'm an early adopter, I love this stuff. Like it's not. I don't just go to googlecom and I have access to gemini. Like I have to go to their labs product and turn things on.

Bill Macaitis: 45:23

It's not that simple right, make it hard right, yeah, and so like so my team uses a combination of these different tools, depending on what makes sense for what we're trying to do.

Rajiv Parikh: 45:32

If it's a coding tool, it was actually Cloud and now it's Gemini, because Gemini has gotten better there. Openai for many of the broad questions. I mean, we're just using all different tools depending on what's better, and I think the game is about abstracting them from the user. Like don't give people a choice, you kind of give them what's best. But, like you're saying, there probably will be a convergence where technical teams may not be doing that anymore. The better tools will figure this out and they personalize, they have memory, they have in-context memory they know what you've done, so they keep you coming back.

Bill Macaitis: 46:02

Yeah and I want that. And the sad thing is like Google has the distribution right. So many like anthropic open-ended. They don't have that right, but they have the distribution. But they're clinging on to the old model. Like I think there's going to be business case studies in the future that are like oh, they hung on to it way too long.

Rajiv Parikh: 46:25

Well, for all those who invest in stock, I think Google's around 16 to 18 price to earnings ratio, which is really low compared to Microsoft. Microsoft's much better. So right now, people are betting that they're going to have a tough time. So you can make a bet on Google right now by a long-term call option if you think that's the way, or don't go the other way. So it's a very this is an amazing question to ponder and I love your hot take on it, bill.

Bill Macaitis: 46:41

All right.

Rajiv Parikh: 46:43

Here's some questions about you. So did you always know you wanted to work in technology Was? There a specific moment or project that sparked your passion. How'd you discover it? What got you sparked?

Bill Macaitis: 46:55

I always loved tech. I had a Commodore 64 growing up for those old enough to kind of remember that. And I love technology, I love software. I tried coding a game once. I had like a big paper manual and literally started writing the code Back then you had to write it in assembly.

Bill Macaitis: 47:12

Yeah, assembly, and I hit run and it was like syntax error line 13. I fixed the syntax error, line 47, syntax and I said you know what, I'm not good at this developing stuff, but I still love tech and I love software and I was so into it and you know, I was at U of I when the web browser started coming out and Marc Andre I was at U of I when the web browser started coming out and Mark Andreessen also was from there and so I was just like I just want to be in the business side somehow. I don't know how or what, but you know I did that and we did a startup right out of college is in the gaming space. We sold that and did a bunch of others on the consumer side.

Rajiv Parikh: 47:40

But yeah, what got you into doing startups like that early? Usually, like you know the thing that your parents would say go make some money first, establish yourself first.

Bill Macaitis: 47:48

I don't know. They were just very supportive of me, like I always knew I wanted to be in business. I always wanted it Like I was a nerd.

Rajiv Parikh: 47:54

Were you reading Fortune Magazine at 12 or something?

Bill Macaitis: 47:56

I was, yeah, I was reading Fortune, forbes, wall Street Journal, business Week, I just geeked out on that. I was such a nerd back then. Oh, I still am a nerd now. But whatever I like that, I like business and it's okay to like it, bill I relate to you.

Rajiv Parikh: 48:11

I don't usually share this very much, but now it's everywhere. My father used to bring home the Wall Street Journal, business Week, fortune Magazine and Time. Magazine, and that would be my weekly and daily reading. Yeah, yeah.

Bill Macaitis: 48:26

I think our parents were smart.

Rajiv Parikh: 48:27

Those are my heroes, by the way, the business folks who were engineering the turnaround. Those are my heroes. So what I love about the business magazine is, unlike news news is always the tilt negatively, yeah Whereas business magazine at least it used to be about these amazing stories of turnaround and these new leaders that are confronting the problem. And then, in the middle of the great turnaround, Absolutely.

Bill Macaitis: 48:50

Yeah, there's so many amazing stories. I still like one of my favorite things now is like I'll get an economist on a long flight and just read it. You know cover to end and yeah, there's still so much greater for me, I think, just like you know, just being curious and always learning, I think like it's awesome, like I said, gold markets is always changing. There's always going to be something new Like you can't just rest on. You know what worked last year, a decade or three decades ago.

Rajiv Parikh: 49:12

You've gone from being a kick-ass CMO to a content creator, so was there a specific pain point that got you to that point to move from one to the other and start SaaS CMO Pro? Was there a trigger that made you decide you needed to be when delivering this as public education beyond private advisory? There's a lot of folks throughout the Valley that do this, that they hit it, they provide advisory, they get on boards and they're known right or, like you, they may become venture partner or venture advisors, but you decided to turn this into a business where you go public and I've seen your episode where you invested a ton into building your own studio and talk about what pain point.

Bill Macaitis: 49:54

Yeah. So, first off, don't build your own studio. It took me forever to do and, although I can go, fancy camera angles and, you know, do all this.

Rajiv Parikh: 50:02

I saw this great movable stuff that's that's awesome.

Bill Macaitis: 50:06

It was such a time. It took me like a year and, for those that do want to have a video on it, if you want to get a good camera, it's a great video.

Rajiv Parikh: 50:12

I saw it. It was awesome.

Bill Macaitis: 50:14

But I think for me there were two things, like one, philosophically, I just knew when I was an operator, like I just wanted to learn, I want other good sources and I kind of wanted to give back right and just help people out. And so all my videos, all my content is totally free, whether it's shorts or long form stuff. I just wanted to help people out. That would be my aspirational good story. The the lazy bad story was I kept getting asked the same questions by founders and CEOs, like how does freemium work, or what does PLG, and I'm just like I will make this video once and not lose, just like send him a link afterwards.

Bill Macaitis: 50:42

Yeah, send the link this is how to do it. Just watch this video, right, like I just sent someone that was wanted to work with me. I sent like 12 videos. I'm like here's like literally like a ton of info and if you still want to work there, great. So yeah, I was like just answering questions that have been answered again, but I just think it's super fun.

Bill Macaitis: 50:56

I just like I love go to market. I really do right, like I don't need to do this. I just because I love doing it and I love working with other founders and even, like it was interesting in the past, when I do my advisory stuff, I'd usually do like series b and above, and now I've started doing like a and even seed round, because there are so many cool pure play ai companies that are coming out that are getting that good product market fit but want help with their go-to-market or want to help grow faster, want help with their marketing and, and for me that's super exciting. If you're a student of business which I know you are as well this is an amazing time right now. Everything is changing and just to be a part of that is super gratifying and rewarding. For me that's fantastic.

Rajiv Parikh: 51:35

I can totally see that in you. So how do you apply rigorous, data-driven go-to-market principles that you use for multi-billion dollar companies to your own content creation strategy for SaaS, cmo Pro and your YouTube channel? So are you tracking creator metrics, content, qualified leads for audience retention on videos, personal brand attributions Are you optimizing your own content funnel in a similar way that you did for your product launch? A lot of times when you create your own content, you kind of want to do it and move away from it, or do you actually want? It took me a long time to want to look at and watch myself again.

Bill Macaitis: 52:12

Totally Well. I so my dad was an engineer and I always kind of came up, was brought up in more of like a you know measure stuff. I can hear him now like measure three times, bill cut once right, that's how you don't make a mistake. And so I always kind of had this measure thing. And when I got into business, I always hated the ivory tower thing where and I saw us a lot of companies and even ones I worked at, where it'd be a bunch of execs sitting in a you know nice high floor in their ivory tower and they were debating like what should go on the homepage and we should use this messaging or this image or this one. And I'm like why are we deciding? Why don't we just test this and let the users answer?

Rajiv Parikh: 52:48

Do two or three versions and test it.

Bill Macaitis: 52:50

Totally right and so, like I've always just tried to be open minded, like, hey, put stuff out, test it. So yeah, there's all this creator type stuff right With. You're looking at engagement and across all the different channels. So that's been really challenging for me is when I went out, I tried to be channel agnostic. So I'm doing stuff on TikTok and I'm doing stuff on LinkedIn and doing stuff on YouTube and all these different ones and it's a learning experience, right. You learn and you're like that worked boy, that bomb, that totally didn't work there. Like I got to make my intro shorter and not just, you know, wax on and I saw.

Rajiv Parikh: 53:22

I saw one thing in just just the evolution on your YouTube shorts. You went from having the music in the background to not yeah, and frankly, it played so much better when you took it out, because you're a compelling speaker in and of yourself and you do add in these little video thing video shorts as part of it.

Bill Macaitis: 53:36

And it was tough for me, cause, like I filmed a bunch of my content at the beginning and then I did a mass, like I worked with editors and AI tools and and I have a. So I have a big chunk of content that, like I've already finished and I'm still releasing and I have another bunch that's like revised Right, and one of the things I found in business is people don't they don't want it over-edited Right. It actually like over-edited, I think smells like it's corporate Right and so sometimes just like a simple, authentic or even just holding like an iPhone walking around, hey guys, like here's how POG works Like I think can perform better. So it's all. These are learning experiences, you know, and I think it's just come with open mind and you know you can still improve. And I asked my daughter what works too. That helps. How old is your daughter? She's 15 now, and so she's always like dad you're, oh my God, like that was cringy. What are you doing?

Rajiv Parikh: 54:19

You have the perfect audience for it. That's great. All right, here we go. I have a bunch of quick question answers. More about you. So what's something you thought that you'd figure out by now, but are still completely confused by Women?

Bill Macaitis: 54:36

That's something my dad would say I love you, honey, amy, you're the best.

Rajiv Parikh: 54:42

But it keeps you. It keeps you together. It does Otherwise you would get bored.

Bill Macaitis: 54:45

I'm still keeping up my toes, still trying to figure out. Does she want my advice right now, or does she just want me to listen to what happened? Right, I think I'm learning that, like usually, I give the advice. I'm like no shut up, bill, just listen and you'll be better Listen till they ask All right, great answer.

Rajiv Parikh: 55:00

What's a question you wish people would ask more often and what's a question you wish they'd stop asking?

Bill Macaitis: 55:06

I wish more founders would kind of like hey, how can we update our go-to-market right? How can we update our pricing? How can we just improve it? I just feel like for a lot of founders and I get it like most founders in the Bay Area are technical founders, right, so go-to-market is kind of new and I just I love working with founders that are like, hey, we want a more modern, clean, go-to-market engine. So, yeah, that's definitely something that's awesome.

Rajiv Parikh: 55:31

What do you wish they would stop asking about? That's a tough one, because you seem like a pretty open and easy approachable person.

Bill Macaitis: 55:38

Yeah, I'm trying to think just something like more around, like an old sales model, like this sales model should work. Like why does no one know about us? Or I don't know? Like usually I'm pretty open minded with all the questions there's no bad questions, right. And I get it Like if I was a technical founder. This is all new. If I'm, if I'm the CEO, if I'm running technical stuff, I'm going to ask a lot of like weird or dumb questions might be wrong or, in your case, you might just openly think they're wrong.

Bill Macaitis: 56:09

Well, we talked about the freemium right. I think people have a really harsh reaction to it and as a marketer and a growth person, I've seen the incredible power that it has, so I'd probably go with that one. That's a great one.

Rajiv Parikh: 56:20

If you could have a 30-minute conversation with any version of yourself in the past, what age would you pick and what would you want to discuss?

Bill Macaitis: 56:26

Oh man, I would want to go back to, I think, my 10 year old self. I remember riding my dirt bike and I remember stopping in the middle of the street and thinking like, wow, I wonder, like what my life will be like at like 50 or 51, like what I am now. And I would be fun to go back and talk to that person and just be like, hey, you know, and here's how it turned out, or this worked or this absolutely did not work. It would just be a fun.

Rajiv Parikh: 56:47

I don't know what's one piece of advice you'd give yourself. You're 10 years old, you're 50 year old self. You're a 10 year old that's actually willing to listen, which is actually 10 is a good age for listening. It's not because 14 is not a good age for listening.

Bill Macaitis: 56:59

Well, I watched a lot of like time movies and back in history and stuff. So I would say like, of course I'd say, don't change a thing, Otherwise I won't be here and I would have met my wife and my amazing daughter.

Rajiv Parikh: 57:09

Yeah, there's that movie.

Bill Macaitis: 57:10

Yeah, the butterfly effect right you know, like make sure you get on this train or move to Denver at this time, or do whatever.

Rajiv Parikh: 57:15

Give them the comic book, like Back to the Future.

Bill Macaitis: 57:18

No, if I had to give myself just always be learning, right, like, just stay humble, know what you know, know what you don't know, and just like hey, just always try to be learning.

Rajiv Parikh: 57:26

Do you have a favorite life motto?

Bill Macaitis: 57:28

Carpe diem. You know, I, I, I end a lot of my videos that with that one and I'm just a big believer in like there's opportunities everywhere and you know, like sometimes just just take it, seize the day, right. You know, just go out there. Life is short, life is precious. You know, my dad's been battling through cancer. That's been really rough and it's like one of those things like you just have to. Every moment is precious right. You just have to like seize the day, like don't don't waste any days, just just go out there.

Rajiv Parikh: 57:53

I love it. What's something that consistently surprises you about other people, either in a good way or a bad way?

Bill Macaitis: 57:59

bad way. I'm always surprised by the humanity, the goodness of people, like, maybe not surprised, but I think some people are like, oh, there's just some people are just bad or this or that. And I always think, like you know, there's just so many good, humble, great people out there like trying to do the right thing. And I even think with business that happens a lot too, right? Like if we make that parallel where you know, if you give a bad metric to someone and they're just going to try to hit it right, if you give marketers leads, they're just going to stuff with as many leads as they can. But it was a bad metric, but there's just good people, right? So I think most people are trying to do the right thing and you know, as leaders and as business people, if we can support them and give them the right metrics, we can take them down the right path.

Rajiv Parikh: 58:37

You know, I think there's too much of this, like you're saying us versus them and it's created a highly polarized environment and instead of the, they're evil, they're awful, they're stupid.

Bill Macaitis: 58:50

Maybe there's a.

Rajiv Parikh: 58:51

Hey, let's understand why you have that point of view Right and frankly, I see this a lot with college kids and I thought college was supposed to be a place where you learn things and learn how to think, and so there's some work to be done, and I I'd love to see, like you're talking about, open yourself up to other folks.

Bill Macaitis: 59:05

Yeah, beginner's mindset Think they're good.

Rajiv Parikh: 59:07

If you start off thinking they're pretty good, you're probably less likely to label them.

Bill Macaitis: 59:12

Yeah, totally.

Rajiv Parikh: 59:13

All right. If you had to teach a masterclass on something that's not your job, something you're genuinely passionate about, what would the course be called?

Bill Macaitis: 59:28

Soil structure and gardening. I really nerd out on that. I nerd out on a lot of things. I just get into stuff. But I love gardening If there's any gardeners out there whether you're talking about like ornamentals, edibles, just across the board I love growing things and I think it's like super fun. Yeah, I've got a bunch of fruit trees I'm growing right now and I've dived way into avocados and nightly temperatures and AB pollination and, yeah, I love gardening. If anyone's geek out on that, hit me up on LinkedIn. That's fantastic.

Rajiv Parikh: 59:50

So thank you for that. This was super helpful. This was one of the best sessions I've ever had. Bill, you're a true pro and I love marketers who are super innovative like you that are now out there teaching and you've opened yourself up so much to it, so I'd urge everyone to take a look at Bill's YouTube channel, SAS CMO Pro. Recently, Bill also, along with our friend John Miller and a couple other folks, put out SAS benchmarks right.

Bill Macaitis: 1:00:14

SAS go to market. Sas B2B marketing benchmarks B2B marketing benchmarks and I think they can get to them if they, on LinkedIn, just ask you Just ask me Hit me up on LinkedIn, say, hey, I want the B2B benchmark report, or literally, if anyone just wants to chat, you know, like exchange ideas, linkedin is probably the best place to reach me. Or you can always go to my site, cmoprocom.

Rajiv Parikh: 1:00:33

Chock full of fantastic information. He's very open and free with Bill's offering, so loved having you on the show, bill.

Bill Macaitis: 1:00:45

And look forward to hanging out with you over in Marin. Absolutely.

Rajiv Parikh: 1:00:48

Hey, it was such a pleasure talking with you. I really enjoyed the conversation. Thanks again for having me. If you're a marketing or business innovation geek, this is the perfect episode. Bill has really thought through his methodology, his way of thinking, his belief system.

Rajiv Parikh: 1:01:01

Coming from the gaming world and applying those learnings, his notion of product-led growth, freemium, and how that applies to today's or even he talked about today product-led sales, which I think is a really interesting subject for people to get into, and what I like about it is, with the channel that he's created, you can access all that. So our objective was to get that extra out of him that you couldn't get from all those places, and we got that today and I really appreciate it. Love his point of view about carpe diem seize the day, grab opportunities where they can be. There's so many opportunities that are out there. He expressed real concerns about what could happen in the AI world and some of it is a leap of faith and it's hard when you have that leap leap of faith and we're all dealing with it. I love his hot take on Google and what they're missing the boat on, and it's instructive. This is one of those things where you have to look and say this is a time to mark and say it's a great debate. So thank you for joining us today. It was such a thrill to have this conversation. I hope you enjoyed it as much as me. Thanks for listening.

Rajiv Parikh: 1:02:02

If you enjoyed this pod, please take a moment to rate it and comment. You can find us on Apple, spotify, youtube, our own website and everywhere podcasts can be found. The show is produced by Anand Shah and edited by Sean Marr and Laura Ballant. I'm your host, Rajiv Parikh, from Position Squared, an AI-driven hopefully PLG-driven growth marketing company based in Silicon Valley. Come visit us at position2.com. This is an effing funny production and we'll catch you next time. Remember folks, be ever curious.