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0:00 Marketing and Technology With Bill Macaitis
3:54 Finding Opportunity in Pain
12:27 Leveraging Metrics for Fun and Success
16:53 Unlocking Membership Growth Strategies for Associations
24:54 Content Creation and AI Integration
30:25 Pricing and Packaging Strategy for Software
39:05 Creating Value and Revenue Opportunities
44:31 AI Impact on Marketing Evolution



In this episode of Sidecar Sync, Amith and Mallory welcome Bill Macaitis, a seasoned advisor and board member with a remarkable track record at companies like Slack, Zendesk, and Salesforce. Bill shares his insights on leveraging pain points as opportunities for growth, delving into the principles of product-led growth (PLG) and how associations can implement freemium models and advanced pricing strategies to drive engagement and revenue. The discussion also touches on the transformative potential of AI in marketing, offering practical advice on content repurposing, personalization, and reducing friction in user experiences. Tune in for a deep dive into modern marketing strategies and AI-driven innovation, packed with actionable insights for associations and beyond.



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This episode is brought to you by Sidecar's AI Learning Hub. The AI Learning Hub blends self-paced learning with live expert interaction. It's designed for the busy association or nonprofit professional.

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More about Your Host:

Mallory Mejias is the Manager at Sidecar, and she's passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space. Follow Mallory on Linkedin.

Read the Transcript

Disclaimer: This transcript was generated by artificial intelligence using Descript. It may contain errors or inaccuracies.

Mallory Mejias: [00:00:00] Bill, thank you so much for joining us on the Sidecar Sync podcast. You have quite the professional history. Slack, Zendesk, Salesforce. Can you talk a little bit about your journey with marketing and technology?

Bill Macaitis: Well, first off, thanks for having me, Mallory. Thanks for having me, Amith. Great to be here. And, you know, I've just been one of those people that always loved business.

I always loved marketing. I was the The nerd in sixth grade in the back that was reading Wall Street Journal, Forbes and Fortune. Um, so I've always had a huge passion for this. You know, I did entrepreneurship club like in high school and, um, have always have done it. I did a startup right out of college and it was on the B2C side.

We grew and sold that. We had a couple more exits on the B2C side. And then most recently, as you said, like on the B2B side with Salesforce, Endless and Slack. So, uh, it's been an honor. I've always loved online marketing. I've always loved, you know, more. Innovative go to market models with SaaS and AI. So I was super excited when you guys reached out to talk today.[00:01:00]

Mallory Mejias: I'm impressed. I was not reading Wall Street Journal in middle school. I don't know about you and me, but I was not so very impressive.

Amith Nagarajan: I was right there with Bill doing that. And yeah, and

Bill it's, uh, it's great to see you. It's been a while. Thanks so much for being here.

Bill Macaitis: Oh, yeah, great pleasure.

Mallory Mejias: I heard on another podcast you did something you said, where there's more pain, there's more opportunity. And I really liked that. I was wondering if you could share some examples of how this mantra has held true in your life.

Bill Macaitis: Yeah, it's interesting because I think, You know, I work with a lot of different VCs and everyone has their investment theses and everyone has different ways of how they allocate capital. And for me, I just always said like, Hey, where there's pain, there's opportunity, right? Like if you can find a space that has a ton of pain in it, there's a huge opportunity to build a business there.

And sometimes it's as simple as that, right? Like the, the daily occurrences we go through, [00:02:00] where's their pain? Where's their friction? Um, ironically, a lot of times I find with these startups, like these older spaces, these older industries have the most pain in them because they, maybe they're not sexy. I majored in business, but I actually had a minor or a focus on supply chain management and supply chain management for a lot of people is really boring.

It's logistics. It's manufacturing. It's warehousing. It's not really sexy stuff that doesn't get like the sexy investment money, but there's so much money that goes through that, that engine and there's tons of opportunity there. Um, Yeah. Yeah. To make a lot of money and to, you know, help these customers out and reduce that pain.

So I think, you know, for me personally, whenever I evaluated if I'm going to move forward with a company and, you know, help them out here as an advisor or as a full time role, I always looked at pain. And so Slack was a really good example. Like I couldn't find anyone. that I knew that really liked using email that were like, I love email and it works great for team communication and it's the best, right?

It was usually just people bitching [00:03:00] about it. And so I'm like, Oh, there's a lot of pain there. Right. Um, and so, you know, for me, that's been a cool kind of guiding compass. That's helped me out.

Amith Nagarajan: That makes a lot of sense, you know, and that's so incredibly relevant for our audience, the association community, both because of the pain points they are so attuned into in their markets, you know, whether they serve doctors or lawyers or engineers or architects or whatever the association is focused on.

They know that domain really well, and they kind of feel the pain, they see the pain, they know the pain, and there's opportunity abundant in that pain. I love that framing, and I think, you know, your example with Slack makes a ton of sense. There's an inefficiency or something that's just troubling a lot of people.

Associations all over, you know, a lot of times they're thinking about like, oh, well, how do you just keep up with doing what you currently do? We try to encourage you to think about the products, services, uh, and opportunities that need to exist in order to solve for the future pain with the curve of AI being as aggressive as it is.

All those professions, all those industries are going [00:04:00] to come rapidly and there's new opportunities. There will be new pains and there will also be opportunities to solve for pains that were previously unsolvable because of these technologies.

Bill Macaitis: Absolutely. And I think too, having A customer centric mindset is really helpful, right?

I mean, a lot of times we look at the pain from our side, right? Like the business side, like, where are we having pain? But I really always like to think about just, you know, what is the pain that the average person's having, you know, your user, your customer, right? Um, a lot of times those pain points are like a pebble in a shoe, right?

Like the first time there's a little pebble there, it's a little annoying, but if you have that pebble and you experience it every single day in your shoe, it gets really frustrating really quickly. So, you know, I always just try to put myself in the other person's shoes and kind of understand where they have pain.

And where there's pain, there's opportunity, right? Um, and if you don't solve that pain, someone else usually will come around and do it for you.

Mallory Mejias: Bill I would call you maybe you would call yourself this as well a master of product led growth especially with [00:05:00] all your history at those companies I mentioned at the beginning of the podcast, but I think it would be helpful for our listeners to go back to the basics. How do you define product led growth?

Bill Macaitis: Yeah, I'm definitely a nerd with PLG. I have two favorite acronyms in my life. Uh, NPS, which is net promoter score, which is a very customer centric metric and PLG, which is product led growth. If I had tattoos, I would get those too, which is how much of a nerd I am on those. Um, so PLG or product led growth, you'll hear a lot of different definitions.

Uh, for me, what it really means is that people are spending more and more of their time in the actual software or app or product that you have, and you need to infuse. your marketing into the product, your sales into the product, your success into the product, your support into the product. You know, there are, there are some people like you'll have your software, your tool.

And again, that's kind of my background is like software and apps and stuff like that. Um, and some people go like, Oh, they'll create all this amazing [00:06:00] stuff, but they'll put it all on their website or their blog. Um, and we'd like to think everyone's going there, but we know like three or 5 percent of your people are going there.

Right. Um, But how do you like infuse all that good marketing and into the product, right? Um, and not only that, but how do you make it a better experience within there? So, you know, when I say like, you know, put your sales into product, that might be, hey, you have a high velocity motion, right? Where people can buy stuff on their own, right?

When you put your success into the product, um, you might have a proactive chat, That pops up and goes, Hey, when someone's using your software for the first time, someone actually says, Hey, you know, I'm Mallory. How can I help you out? Like get this started and get it going. Right. Versus, you know, the old way, which is very reactive, which was, Hey, you would wait until someone had a problem.

Then they'd have to leave your app or your software, go to your website, find the contact us, find the support link, find the email link, send a request, wait three weeks, get a response, go back into it, such [00:07:00] like a, You know, terrible experience there. Um, the, the other big tenants you have in PLG is you want to have, um, a fun product, a simple product, right?

And so you spend a lot of cycles on that. And that's where like, when you say put your marketing into the product, you know, a lot of times you'll go to the website and it's beautiful. It's got like mascots and all these colors and it's fun tone. And then you go into the product itself, the software. And everything's like, that's all gone.

It's all like white background, black text. Everything is next, except cancel. It's like, whoa, where did all the fun go? Right. Um, and what I found is when you can make a product that is fun and simple to use, people tend to talk about it more. People tend to recommend it more. Uh, so as an anecdote, like Slack, our number one integration for as long as I was there was not HubSpot or Marketo or all these business applications.

It was Giphy. Right? Everyone wanted to tie an automatic giphy in so you could just do backslash giphy [00:08:00] and put a fun little, you know, image in there. Uh, people want to have fun with it. And so product led growth is all about how do you infuse your marketing into the product? You know, unique visual identity, tone and voice.

How do you infuse your sales into the product, high velocity? How do you infuse your support and success into the product? How do you make your product simple, more fun? And it's very antithetical to how most people do it. companies build their products because most of them just add feature after feature after feature.

It becomes, the more features you add, the harder it is to use, the less fun it is to use. You can't buy it in the product. You have to talk to a salesperson. You, you know, it's hard to use. So you have to go to a customer success person. Um, it's just a different way of kind of building more modern AI and SAS tools.

Amith Nagarajan: That's super helpful. And I love the description and the example in slack. I certainly experienced that myself. And I think it's fun. It also adds utility fundamentally to the modality of communication people can have in a product like that, where you can really express yourself in ways that you probably wouldn't in a business setting without it.

[00:09:00] So it kind of adds richness to the experience. Beyond just the enjoyment, it's, I think, a really powerful modality. And, uh, I think associations generally, I would say, you know, it's a generalization, but are, tend to be a little bit on the dry side with the way they deliver content. So, if you're in a profession, let's say, like, you're an association of surgeons or an association of accountants, Um, do you have any tips on how you might approach still maintaining the seriousness of the domain, but maybe finding creative ways to inject something in kind of that fun realm?

Uh, I think there's probably lots of ways to do that, but I'd love to hear your reaction to that question.

Bill Macaitis: Yeah, no, it's a great question. And, you know, I've been a part of associations and I tend to agree that the content tends to be a little bit dry, right? And everything tends to be super, super, uh, you know, a little rigid if you will.

So I probably say like, Hey, if you kind of believe in the product, the growth. You're gonna, you're gonna use some different metrics, right? So, uh, two really big metrics we used at Slack [00:10:00] was, uh, daily active users. So that is literally just how many people come to your software every day. In this case, how many people are coming to your association?

Maybe the website, the resources you have, how many are coming every day, right? Um, the other metric we used was net promoter score. So I mentioned earlier and P. S. Um, simple question. How likely are you to recommend to a friend or colleagues? Scale of 1 to 10. It's a cool metric because so many companies use it.

That is super benchmarkable, right? You can just see pretty instantly like two people. Are they getting value out of your service, right? Would they recommend it to someone else? When you start tracking those two metrics, you start taking different strategies, right? Um, yeah. Because, you know, to your question, like, how do you make it a little more fun?

Well, when you have a fun product or a fun service or a fun association, people tend to come more often, right? They tend to visit you more. Um, you know, when people visit you more and they like you more, in general, I found all the sumps, substream revenue metrics tend to work out better. They tend to pay [00:11:00] more for you.

They tend to renew more. They tend to a trip less, you know, so I think like when you can create a valuable service that people are coming back more often that they really like that, the recommending, you know, all your other metrics tend to do very well. And that's a good, those are good input metrics. I think like a lot of times revenue metrics or output metrics, um, You know, you have to improve the input metrics to get the output metrics to improve.

And so I think there's lots of easy ways to, you know, make your product more fun. Even the association, like one way is like, Hey, find a lot of times like the websites or the, you know, are built by the backend developers and like have someone that's good at copy or that's just who's the funniest person, you know, right.

And have them rewrite your, your onboarding dialogue, right. Like in the actual website or in the email threads. You know, maybe infuse some, some colors and palettes into that association website. Um, you know, maybe have some more real authentic conversations or just think about like the content that get with people that [00:12:00] they would enjoy more, right?

That maybe they're going to laugh a little bit. Um, I, I think those are all easy ways to kind of get some, some big wins there.

Amith Nagarajan: I think, um, you know, one small idea might to get bigger opportunities and bigger ideas and building on what you just said, you know, you might have a very serious piece of content, but the way you frame it and the way you can navigate people to it, the way you kind of help them approach that content could perhaps take it.

A little bit lighter tone, a different style. Um, one of the big opportunities I think that's out there with artificial intelligence and this type of interaction is this degree of personalization that we can approach in our individuals with where, you know, you might actually adjust the tone that you engage with a particular person and say an environment like a learning management system.

Let's say we're in associations for brain. Professional education. Um, perhaps if I know I'm talking to Bill and he's a fun guy who likes a lot of humor and he likes a lot of color, I can perhaps still stay on brand, but within certain, you know, kind of characteristics, give Bill a little bit different experience [00:13:00] than perhaps somebody else who's very serious and different personality style.

Of course, AI, you know, uh, it's exactly what AI is so, so good at now. Um, another aspect that I'd love to get your feedback on that I think is incredibly interesting from a marketing perspective and also PLG within, within the environment of a product is storytelling. Um, you know, we, we know that kind of the emotional bond we form with narratives, with stories when done well is incredibly strong and the retention we have is so much higher than just kind of the dry dissertation of facts and figures.

Uh, yet we don't do that in business communications. We don't tell stories live. And once again, we have language models. Particularly as they continue to relentlessly improve, opportunities to potentially do a form of translation. You know, when we talk about translation, people immediately, their brain goes to like, English to Spanish.

Which is amazing. That's unbelievably exciting. But what about translating, um, a piece of content into a vibrant story? Um, and then delivering that story and seeing if you can [00:14:00] deliver the same educational insights, but through storytelling. What's your reaction to that kind of approach? I'm just curious.

Bill Macaitis: I love it.

And I feel like there's so much opportunity now if you are anywhere near if you're an association and you're dealing with content, like AI is one of the most singular powerful drivers of your future success. There were so many use cases for and you guys knows where you can leverage AI and I think a huge part of that that not as people tap into is the tone and voice.

Um, and I think it's actually great news because not everybody's just like this phenomenal writer or phenomenal storyteller, right? But if you have kind of the existing content, maybe you have that white paper Maybe you have that data research paper, right? And you can pull out these compelling stories these compelling Um, customer use cases and give them emotion behind it.

Right. And you can change those tones to what is relevant for your audience. Right. And maybe you said, maybe it's even a one to one personalization level. Um, you know, the capabilities are just incredible. [00:15:00] And you know, 4. 0 and Gemini, and there's There's so much new advances. And you know, I, I, I loved what Sam Altman said recently, which was, and it was before he launched 4.

0, but he's like, the current LM you're using will be the most dumb LM you will ever use in your entire life. Right. So that's like, it's pretty good right now. Right. So, um, yeah, there's so much opportunity there and I love the personalization. I love the tone. I love the refactoring of existing contents. Um, there's tons and tons of opportunities for, for associations right now.

Amith Nagarajan: One of the related opportunities we think about is kind of thinking about market adjacency. So we think about like, oh, I'm an association for CPAs and so that's a pretty narrow audience in a sense because the number of people that are in say the accounting profession at large Is far greater than the number of people who have the CPA designation And then of course beyond accountants people who are in kind of the financial office in other roles They're not accountants, but are related to it And you think about the amount of [00:16:00] content a CPA society might have that could be relevant to the broader audience.

Going right back to what you just said, um, there's opportunities for repurposing, refactoring, different kinds of storytelling. And a lot of associations try to, they kind of stay in their lane. They think of it from the viewpoint of, like, who are their traditional members and who have they, what have they wanted?

I think there's opportunities to do what you're saying and, and, um, Potentially considering these adjacencies.

Bill Macaitis: Yeah. I mean, there's so many great adjacent markets, you know, I'm always surprised with uh, these associations I know i'm part of several and it's like I mentioned a lot of other things too that you know Maybe go just a little bit outside of that edge and I don't think you need to be as rigid with it I think a lot of times too You know i'm a big believer customer centric and part of that is like You you bring to life the stories of your customers, right?

Like when you hear from You your actual users or people that are part of the associations and you can help bring those stories to life. A lot of times they're so much more powerful than just a data sheet or, you know, a white paper or something like very technical with just [00:17:00] tons of stats. Like people remember stories and it's amazing when people bond with those, those stories, they create relationships and again, they're much more of an advocate for you.

They go to bat for you. So, um, I think it's, I think it's critical for an association to think about that.

Mallory Mejias: I'm big on the stories. I will say that just is my two cents. Bill, when talking about associations, you're a member of some, you know that we're talking about membership models a lot of the time. And so when defining product led growth, you mentioned infusing marketing, sales and success into the product.

But can you help contextualize how You could use those same strategies with a membership for example.

Bill Macaitis: Yeah, so i've done Memberships pretty much for 30 years now online memberships, right? Like my first startup out of college We had a three tier subscription model It was in the gaming space, but you could sign up for like You know a gold membership or platinum membership And we started too high in the precious metals because then when [00:18:00] we added a third one We're like, what the heck do we what's better than platinum?

So we're like diamond, right? You know um, but yeah, I think memberships are Really amazing way to build recurring revenue, right? That's a big part of like SaaS, the space I'm in, software as a service, is you have recurring revenue as part of a membership. And I think there is a huge art in science to how you price and package these things.

So, um, I tend to be a big believer in the freemium model. That's usually a key tenant of of PLG is you want to get people into their product and start experiencing value before you force a purchase decision on them. And so what I find is a lot of companies, especially in ones that are more traditional industries or a little older school, have a really hard time with that.

And a lot of time, it's like, hey, you get all this stuff, but you have to pay us before you access any of that value. And historically, when I've seen companies go down that route, they have very low conversion rates. Right. They'll usually get, you know, usually free to paid as like one to five percent, um, [00:19:00] kind of industry average.

But, when you start to experiment with these pricing models and you start to open it up to have a little bit more of a free model, um, people start to experience a lot of value. And then you can think about what are your triggers to upgrade differently. So, uh, for instance, a lot of people use features to differentiate their plans.

You know, on plan A you get, you know, These five features on plan B, you get the next five features on plan C premium. You get the next five. Well, what a lot of companies a little more advanced are using thresholds. So what they'll do is they'll say, Hey, we're going to offer a free plan. And by the way, it's not even a crippleware plan.

It's not like you only get two features and you only get to use it for like, you know, three days and then your access gets cut off, but they'll say, Hey, you get a free plan and you get to access almost all of our features, but we're going to put some thresholds in, right? So for instance, for open AI, for instance, since you can say, Hey, you get to use once a day, you can go in and use it, but Hey, if you want to use it more than once a day, maybe you need to go to this next plan here or for Slack.

For instance, we said, Hey, you get up to five integrations on the free plan. If you want to go beyond that. [00:20:00] You, you know, you need to, you need to upgrade. Um, and so I think those concepts are really powerful, uh, because at the end of the day, so anyone that's in an association, anyone that's marketing an association, you know, you generally have a directive, right?

You have to go out get X amount of members, and usually it's like we want to get more members, right? So how do you get those members, right? Okay, give me a marketing budget. I will use a lot of different media and Essentially buy users to come into you. Well, when you kind of have a free model, what ends up happening is you end up having, it's like, you're hiring these marketers on the free plan, right?

So it's like, I mean, that's, we had like a million for users. I didn't look as we had a million for users. I looked as we had a million free marketers, right? That were out there talking about our, our plan, recommending it to other people, getting other people to sign up for it. And so, you know, for me, it's a long way of saying like a free user is a bad thing.

It's actually like, it's a marketing cost, if you will. Um, and that marketing cost a lot of times is cheaper than the alternative forms of demand gen or paid media that you're using. [00:21:00] I'll and find new members. Um, and then also if you layer in these more advanced strategies with thresholds and other things, you can get really much higher conversion rates because now people experience the value.

They see it and they're like, Oh yeah, I get this. Oh yeah. I want to upgrade to the next plan. Cause I want to have more unlimited access to all this, right. It's a very different cell then. You know, putting everything behind the gates and you have to make this huge purchase decision right off the bat, if you're going to move forward or not.

So those are some kind of core concepts of PLG and how they could apply to more subscription model.

Amith Nagarajan: I think those are on the, you know, pretty much bullseye for the association market. Uh, you know, back in 2017, I published a book called the open garden organization, which was targeting exactly this topic.

I was trying to encourage associations to reconsider their strategy to focus. Uh, not so much in a defined customer group, um, that they've oftentimes had 80, 90 percent market share with already, but, uh, to think about the broader context of where they can provide utility and, um, and to do exactly what you're saying, to make some content available, to open the [00:22:00] garden, to bring people in, to share some of those resources, which of course advances their purpose since these are all Not for profit purpose driven organizations or almost all of them are and then of course that creates those opportunities for funnel activation You know downstream where you can offer higher value for higher investments, so Love the model I think that one thing that I would say is I think kind of interesting for associations now to consider what that is There's a lot of concern about content that's freely available, not so much because the economics, but because of the broader world and AI Models being trained on them.

So you put all this great content out there as a marketer Maybe some of its behind a paywall you have to register, but it's still free with that style of freedom Maybe some of it's just like traditionally SEO enabled content to bring people in And the concern is, is that Google with generative summaries, um, or other search engines, you know, don't even have to send the traffic your way.

Um, what are your thoughts on that? Just, it's on topic, but a little bit to [00:23:00] the, to the side of the experience. How do you feel about that?

Bill Macaitis: Man, it's, it's the million dollar question, right? That every content creator is thinking about, is worried about, you know, is my content. Um, Just going to be put out there and and essentially, you know trained for someone else that can use it I know there's a part of me that's just like, you know, if you're trying to hide your content, are you just You know, fighting gravity, right?

Like there's so much content out there and I don't know, maybe you're the one that has this completely unique take on it that no one else has. But part of me is like, Hey, you're just fighting it. Like there, there's so much content they're going to get trained on. Another part of me is like, Hey, maybe you can monetize that down the road.

Right? Like some of these services are starting to go to individual companies and pay to for their content to be trained. And obviously we'll see how this settles on the legal side with like the New York times and a bunch of other media companies. But, you know, there's, there's. You know, recently announced deals with the Reddits and some other services where they're trying to get that content.

So hey, maybe that's a future revenue stream for you. Um, I don't know. I mean, at the end of [00:24:00] day, like when I have these tough questions, I just kind of always go back to all right, well, what would my, what would my customer like? What would my user like? What my viewer like? Right. And if I can provide utility and value to them, then that's generally a good thing, right?

And so, um, I wouldn't, I wouldn't let it completely drive you, you know, to not, um, putting it out there, right? If you will. Um, I just think at the end of the day, you know, my guiding principles, what's best for our users and can we make their lives better? Can we eliminate some pain? Can we provide some value?

If it is, go for it.

Amith Nagarajan: That makes a lot of sense. I think lowering friction for the users, creating value, making it easier, uh, is super important to the point you made earlier. Associations do often have something quite unique. They typically, why I would go so far as to say, often have the best content in their field or their subprofession in the world.

And so they're productive of it on the one hand, the flip side of it is, is they tend to make it kind of hard for people to get to, uh, even their members who are paying, there's a lot of backflips that are being done to just [00:25:00] navigate websites. So I think it's an interesting balance. And once again, going back to the earlier part of this discussion, you know, AI is really good at kind of transformations of content where you might have these deep, rich resources and you just want to put a summary on your website that's public facing outside of the paywall and, you know, that would have normally taken hundreds of hours or thousands of hours and been a non, not a scalable solution, but you can do that with AI where you just publish the summaries or publish some component of the content.

Bill Macaitis: I'm a huge believer in content marketing. So anyone that's part of an association that's creating content, like, Hey, love you. I've, I've been there like Slack, Zendesk, Salesforce, Weech. I built up really large content teams. Um, and I'm a huge believer of creating, you know, great evergreen content and then reusing that and repurposing it.

Right. Even now, you know, it's like the Mallory, like I'm filming a bunch of content for an upcoming YouTube channel that I'm going to be doing. I've got a lot of the long form content down, but now I'm like, I'm, you know, chopping it all up in the shorts, right. And, you know, reusing it in different places there.[00:26:00]

And AI has been hugely helpful throughout that entire process, right. For me as a content creator. So yeah, like I, I would always tell my content teams like, Hey, focus less on quantity. This is not like, Hey, we have to get a blog post per week. Think about more evergreen content. Good great big evergreen content, and then how can you use that in as many channels as possible?

How can you slice it up into different areas? You know video is a huge part now, too You see like LinkedIn is launching kind of a you know a video tab right within their mobile app Which is kind of new and cool The explosion of all the different social channels. So I think in a great way, like all the associates, all the associations out there, Hey, you have really great and unique content.

Now it's just a question of how do you leverage it? And I think I is like a huge part of it can be a great asset to you to make that process, you know, so much easier.

Amith Nagarajan: The other question I wanted to ask you is, when you think about your funnel strategy, going from free to paid, um, a lot of associations, it's kind of like, you know, going from [00:27:00] hanging out, um, at the Ahwahnee Hotel at the base of Yosemite Valley, enjoying a cocktail to scaling the face of El Capitan, right?

It's like the straight vertical leaps or something. Very pleasurable and enjoyable to like, oh crap, I'm not going to do that, right? Um, what about, you know, some kind of a tripwire offer, something that's just a very small Little purchase. Yeah, I'll give you one example of what we do. The sidecar effectively is like an association.

We don't have members, but we have the concept of, of a very, very similar engagement. And we do a ton of free content. We actually have a free book on AI for associations. We talk about a lot. We have this podcast, we have a free monthly webinar on AI for association leaders and on and on and on. And then we have this 25 thing, which is this mini course we call our prompt engineering Uh, boot camp or mini course, I think is what we call it right now.

Um, and the idea is we, and we also have a 400, uh, learning hub, which is a much bigger like investment in learning. And so what we're trying to do is get people to convert from once another to [00:28:00] the next. Um, what are your thoughts on some kind of a little bitty, but paid offering that precedes membership, maybe to get kind of people warmed up to the idea of spending money with the association?

Bill Macaitis: Yeah, I love the idea of having, you know, ladders, easy steps that you can make, right? Um, again, kind of getting back to PLG, it's all about friction, right? Like how much friction are you putting? And that could be pricing friction, cognitive friction, adoption friction. You know, the more steps, the more clicks, the bigger price jumps, um, those are all just big friction moments, right?

And what you tend to see with those is just very low conversions, right? So I think anytime you can create a smaller offering, you know, that just gets someone in that dips their toes. Now, you know, I would argue, Hey, a lot of that you can do via freemium, right? And, you know, create the right thresholds and, and upgrade drivers, but even having, you know, some, some different plans and easier plans, maybe some one offs, uh, a big part you know, my business is how do you cross sell cross pollinate users that [00:29:00] have expressed a little interest, right?

So, you know, hey, they've signed up for one thing, but now, okay, they've gotten some value on it. You've built up trust and now you can cross sell them, you know, or expose them to everything else that you have. Right. Um, and sometimes, you know, those little steps are a lot easier for these users to get into.

So, yeah, I realized I kind of the old model was, uh, just. You go from nothing to a hundred, right? It's like you have this giant cliff and you know zero to a hundred and hey you have to make that decision Not based off much value not based off a lot, right? You're just kind of making that big leap of faith But I feel like there's better ways and you know the software industry I think in a lot of ways like we all take inspiration from everywhere.

Like I take a lot of my inspiration from Uh, like, B2C and gaming, right? Because I did a lot of that, right? And a lot of these things, I think a lot of our personal lives, we probably at some point downloaded some game on our phone, right? And they have, like, really good freemium models, like, they have where you, hey, you sign up and then, oh, you, [00:30:00] if you upgrade, you get these additional points or you get this additional armor, you get this additional, like, levels, you know, and they're really good at, like, slowly working you up to more of a paid user.

Um, And I think we should be inspired by that. You know, all types of industries that have gone through essentially the same kind of complex, uh, problem sets that we're going through. We can be inspired on their solutions.

Mallory Mejias: You mentioned price jumps, which is I think an important piece to dive into.

Sometimes when upgrading from one tier to the next, we can see really large price increases, maybe even 5x in terms of price per user. Can you share any guidance on pricing strategy and how to approach that?

Bill Macaitis: Yeah. Uh, I love those multiples. I've generally gone a 2x, 3x, 3x. Um, so if you have multiple tiers, I like a free tier and then a, You know, a two X from the first page, the second page, and then a three X from the next one there.

Am I getting there right? And then when one more three X, essentially what I found, if you want to distill it down to just easy [00:31:00] to understand language is that, uh, your SMB market. So the, the, the, the people that are in SMBs are the most price sensitive, right? And they are ones that are like. gonna fight you on a dollar increase in price, right?

Um, the further you upmarket the, the, the least price sensitive they are, right? And so you can get, you can have much higher increases on the high end. So, you know, when I would tend to look at it, Uh, again, I, I look through the world a lot in the NPS lens. So net promoter lens and in that lens, you either have promoters or detractors, people that love you and are talking about you or people that hate you and are saying, stay away from that, like the plague.

And so you want to build an army of promoters, right? And so generally you'll make your money on those higher tier plans. Like the enterprises, that's where you tend to make your money. But you still want to have really affordable plans because you want to build an army of promoters, right? So the lower segments, generally, like we would always look at as, hey, again, that [00:32:00] was our marketing engine.

So the free segment and the SMB segment, like the first, the free plan and they're really low. That first low price plan was your marketing engine. Think about the money you spend on marketing. Think of almost like, Hey, that's, you know, the bandwidth costs for those users, the support costs for users.

That's, that's essentially, that's a marketing write off. And then as you go higher up in the plans, that's where you tend to make your money. The problem is if you just skip straight to the higher up. And by the way, I say this all the time. I, you know, I currently serve as an advisor, um, board member for a lot of SaaS startups.

The number one thing they come to me with is. Bill, we've got a great product. We sell only to the enterprise. Um, but no one knows us, right? And I'm like, of course we have like 75 customers. Now, maybe they're spending a million dollars each, but you literally, you have like, there's only like a hundred people in the world that actually use your product.

Right. And there are 7 million people in the world. So that's a, that's a 0. 0000. Right. Um, but the companies that I've seen that have You know, have these lower price tiers tend to have just a lot more users. And again, [00:33:00] users that normally wouldn't sign up for you because they're price sensitive. So if you have a, you know, an intro price that is relatively, you know, reasonable, you're gonna have a lot of those users.

And then all of a sudden, You get like this, uh, this flywheel effect. The more users you have, the more people know about it. The more people that want to work with you, the more credible you are, right? It just starts rolling and you start to become the, you know, the industry category leader for that particular space.

So I think it is important. Like I do like multiple tiers, right? Where are you doing per user? Um, you know, UBP or usage based pricing is a big thing in the software side as well, and that's essentially allowing you to have multiple tiers, right? You can just start small with a little bit of usage and as you use more, you Uh, you, you, you pay more, but those, those concepts are really important, right?

Like have, I recommend have multiple tiers, have a free tier. That first year should be just, you know, not that much at all, a little bit. And then you can pretty quickly scale up, um, to those, those higher, you know, gold platinum type tiers.

Amith Nagarajan: That's super helpful. You know, I remember the conversations we [00:34:00] had with you, Bill, back in the days of, uh, when we were starting Rasa and Bill was an advisor to the Rasa team.

And, uh, we talked a lot about how at the higher tiers, you'd also sometimes package in certain features that were mandatory or really highly desired at bigger enterprises like SSO or provisioning capabilities or certain types of document retention or those kinds of things that really appeal to people that were focused on governance or security or purchasing, etc.

That didn't really affect the users, the end users that much. Um, but they provide enterprise level value. There's value at the board level, even though the individual wouldn't necessarily discern the difference. Can you talk a little bit about that?

Bill Macaitis: First off, I mean, I'm so happy you remembered that. Um, that is like my advanced pricing and packaging course, and you just got an A on it, so well done there.

Um, yeah, so this is, uh, I mean, I love geeking out on this stuff. And I would say this isn't a really advanced level pricing and packaging strategy, which is great. Which is there's two ways to get people to upgrade. I talked about one, which is the [00:35:00] threshold model, right? So you basically have it a feed at a user feature level.

You want all the features that your users can access at any level, but you'll put something on a couple of them. You put thresholds, right? You can only use it X amount of times per month, per year, whatever it is. The other strategy that works incredibly well. Is to put the enterprise requirements for those highest tiers that you have.

And you mentioned them, you know, provisioning, deprovisioning, SSO, compliance, exports, legal, consolidated billing, dedicated customer success manager, 99. 99 percent SLA uptime stuff that just like enterprises have to have, right? Like, like if you were a Slack user, you know, and something happens and you leave the company.

You don't want that person to still have access to slack, right? That's like all your company stuff. Like that's a huge legal compliance risk. You know, an enterprise has to have that. Now, is that a feature that a user using slack? You know, it has. No, they're not. But what that means is now [00:36:00] you've reduced the friction.

So a ton of more people can start using that service there. So I always think that's like a really great way. Um, and again, that fits in with the PLG model of like you're getting your products in much more people's hands. So you're increasing your awareness. It's subsidized marketing, and you're still creating these natural upgrade drivers.

But it allows for more seed and grow. It allows for you to get like little pockets of usage in these large enterprises. So yeah, it's a great strategy. I don't see as many people using it, but really powerful for the ones that embrace it.

Amith Nagarajan: So Bill, I think you'll like this. Not only did I remember what you taught us at Rothset in those early days, but we actually wrote about you, not specifically by name, but we wrote about that strategy in Chapter 6 of the book that we introduced on AI for Association.

Awesome! And there is this exact concept of going upstream with, you know, basically it's asymmetrical, you know, type of model in terms of value relative to cost. And the value creation is massive. Sometimes it's mandatory by, you know, Sarbanes Oxley or something. Sometimes it's something different in the association [00:37:00] market.

I wanted to contextualize this for a minute with an idea from that chapter of the book and get your, get your two cents and try to translate a little bit of the SAS world that you described for our listeners. So, um, value creation in the context of association. So let's take, uh, for example, an association of teachers.

Uh, so the association of teachers delivers education to the teachers. Maybe they have like a lot of templates and lesson plans and, you know, content that the teachers can use to do their job and do a better job as educators, which is awesome. And so they have a membership, and there's a high degree of price sensitivity amongst their audience.

They definitely aren't going to see significant change in that over time. And sometimes, by the way, in these associations, membership structure, both in terms of levels, if there are any, and price, are controlled by extremely strict governance structures. Like, even in the bylaw, this is the organization where they cannot change a lot of this stuff.

It almost takes an act of God for them to be able to change that kind of stuff. We kid, but it's really close to the truth. Um, but the idea might be to have some premium product beyond membership, [00:38:00] right? That might encapsulate some of these higher end things. And coming back to the teacher example, um, So, there's actually some teacher associations in our ecosystem that are rolling out AI bots.

Which are much like ChatGPT, where they will load all of their proprietary content into that AI, and the AI will be then a, uh, of service to the teacher. So the teacher might go to the AI and say, Hey, give me a lesson plan for this particular topic. Which of course you can do in ChatGPT, but that's based on the world's content.

Sure. And not an association's expert level content. So there's significant value there. And so they're packaging that as a member benefit, which of course is awesome for members, it's an extra thing. People who are not expecting previously the association now, you know, it's a good reason to stay there, it's a good reason to join.

Now, if I am the school district, and I look at that and I say, that's awesome, but my school district has certain standards. My school district requires that all of the lesson plans be accessible, all of the lesson plans take into account multilinguality, all [00:39:00] of the lesson plans take into account certain other standards that might be legal standards or just professional standards that my school district has in place, and I have my own content that I want to make sure is woven into the box thinking and the recommendations and the crafting of the lesson plans.

That would be kind of like, you know, the corporate standards, the corporate governance, right? And so the thought process we had was, well, what if there was a radically higher premium level of service from this bot from the teacher's association that could incorporate that school district level or even school level content and it overrode, essentially, if there was conflict, the teacher's association's base content.

And then now the school district says, yeah, now we're good because we know that our content will prevail in the event of a conflict between our standards and the state level standards. And, you know, our thesis was essentially that's dramatically greater value and therefore potentially, uh, you know, 10x, 20x, 50x, whatever the number is, increase in value and therefore revenue opportunity.

Um, what's your reaction? I think there's a [00:40:00] little bit of a parallel to that between, you know, how slack would sell something that had an enterprise great feature. What's your reaction?

Bill Macaitis: Yeah, I think that's, um, it's in that you're distilling it down to the core elements, right? Like, hey, is there pain?

Teachers need lessons plans? Yes. Um, is there also pain at the district level, right? Like, hey, these we want our teachers to be, uh, Putting together these lessons plans in a way that is accessible and is compliance and has everything else that they have pain points, right? And you're using more localized LM's that have been trained on your, you know, your best practices, your data, your compliance to achieve that.

So I think that's hugely valuable. And wherever there's value, you know, there's opportunity, right? To, to monetize that and to price it and to, to help people out. So, yeah, I mean, and I think that's like such a cool thing with AI now, is there's so many of these use cases that are coming out that in the past you couldn't do right, you couldn't, you couldn't just be like, Hey, I'm going to translate all my, my lesson plans into, you know, [00:41:00] 28 different languages.

Right. But now you can do that in. Five seconds. Right. Um, and so I think there's incredible amounts of value. I know it's scary. I know a lot of people listening to this, including myself, that's like, wow, ai, this is scary stuff, right? Like, what's gonna happen? What does it mean for me? What's it mean for job?

I mean for, you know, this industry, but there's so many use cases that are coming out and a lot of 'em are really good and valuable. And I think just, you know. Keeping your ears open and, and being inspired by cross industries and how they're using and think about how you can use it for your particular spaces, uh, is very powerful.

Mallory Mejias: Well, I think that's a really good segue. I had to ask you, Bill, what are your top marketing use cases? You personally, maybe top three marketing, sorry.

Bill Macaitis: Oh, Oh, AI use cases. Yeah. Uh, so yeah, right now I am knee deep. I'm creating. Uh, my own YouTube channel. It'll be called Sassimo pro might be out by the time this, uh, comes out here.

And so [00:42:00] I'm creating just a lot of content myself. And, uh, as we've shown earlier, I've got some different video angles here for the studio, which is a little bit crazy, but, um, a lot of what I use is, Hey, going through that process. So choosing that name Sassimo pro I, I've looked for a lot of AI that helped me out here, you know, choosing the topics that I talk about.

I use AI to help me out there. You know, the editing process. Um, I use A. I. There, uh, you know, there's it's it's unlimited that the thumbnail titles, you know, that I come up with, um, There's so many potential use cases and for me those are the ones I also just found myself I'm using AI a lot more now like as opposed to just going to Google and searching and I know they're Embedding Gemini and into the results now, but I'm going more to just pure play AI tools and asking those questions, right?

And you know, it's, it's fun. So I have, um, my, my channel Sassimo Pro, we have a sloth. That's our [00:43:00] mascot. I love sloths. They're so cute and they move so slow and it's probably the antithesis to modern marketing and efficiency and productivity, but I just love them. They're awesome. Well, like as we're making these videos, I want to have like fun things that a sloth would say.

And so I like the LOL cat style of talking. It's when they're like, it's like when a cat, you'll sometimes see it in memes when they're like, what's that? And they use like Z's and other ones. And. It's a hard, it's a hard style to speak in and I'm not that good at it. So a lot of times I'll just go to like chat GPT and be like, Hey, what would a sloth say in a cute LOL cat like style of speaking?

And it will come up with five different variations of that. Right. And then, you know, I'll, I'll put those into my video. So, um, I just think like, it's one of those things that it's just so powerful. And I think we're all there. We're all starting off slow and we're like, how do we use this? And you're trying to tinkering and, and here's someone else that used it in a really cool way.

You know, either professionally or personally. Um, but for me, those are some of the use cases that are at least top of mind for me right now.

Amith Nagarajan: Bill, if you're talking to someone who hasn't used AI much and is [00:44:00] overwhelmed by it, what's your advice for them to help them get rolling?

Bill Macaitis: Uh, I think, you know, use services like yourself, you know, download, like I listen to a lot of podcasts because I take a lot of walks.

And so I like downloading podcasts, people just talking about it, you know, and just start trying it. I mean, I'm almost saying like, Hey, really easy and that's fine. Like we've all. Essentially hadn't used it at all. And then we all started, you know, at some point we have to start. So what I would say is like, Hey, the next time you're going to go to Google to just put something in, go to like chat GPT and ask the same question.

Right. And just start seeing what it comes up with. Um, the other thing I've started like really trying to press myself on is, Hey, during my daily life for all the stuff I do for my professional, you know, work type stuff, I I'm really trying to ask myself, where could I, where could I eliminate some of this?

So in other words, like, um, Right now like I I'm putting here these videos I have a lot of different camera angles and I'm working with outside video editors But there's already AI tools that can start [00:45:00] taking a long video and chop up, you know, five or six great little minis from it Right, that's awesome.

Now that they haven't figured out yet for multi camera, but at some point they will right? And so I think it's really interesting to just kind of ask yourself. Hey, where do I spend the most time on? Right. Like I remember one task, I was going through all these videos and I was like, ha had to delete one camera angle.

That didn't work. Go back and forth. Go back and it took me like an hour. Right? And it was a very repetitive task. And I, I know at some point, like an AI companion or copilot or agent could have just watched me and said, oh, I can do that for you. Right? So, um, yeah, I'd say start small. You know, listen to some stuff.

It's intimidating at first, but the more you dip your toes and it's really not that bad. It's like going into a pool like, Oh my God, the water's cold. I can't go in. Then you're okay. You get it. I'm swimming. This is great, right? It's uh, it's not that big of a deal.

Mallory Mejias: Have you tried out the tool Munch, Bill? Uh, no,

Bill Macaitis: I don't think so.

What is this? Opus Clips I have, yes. Munch I haven't.

Mallory Mejias: Munch is, I think, similar to Opus Clips. Actually, [00:46:00] yesterday in our Intro to AI webinar, or Tuesday of this week, someone asked if they were similar, and I haven't used both. We typically opt for Munch just because Honestly, I think that was the first few ads I'd ever seen, so I said I'll go with, I'll go with Munch, but we take this podcast, this very episode, we'll drop into Munch, we'll generate some clips that we share on social, we also use the transcript for blog ideas, and social posts, and I don't know if you've heard of the term Content Turkey?

Have you ever heard that before? I

Bill Macaitis: don't know. I haven't. I'm, I mean, I'm learning stuff on this one. I love it. Go for it. I

Mallory Mejias: know. So I, the first time I heard this was actually from Erica, who's the COO of Rasa, um, who you might know, who you probably know, but she, um, on a panel said that a content Turkey is inspired from the idea of a Thanksgiving Turkey.

And you know how the next day you take the leftover Turkey and you make all these variations of meals with it. So basically the podcast is our content Turkey, and then we produce all this other content from it, using AI. So I thought I'd share that with listeners. It's a fun one.

Bill Macaitis: That's a fantastic one.

That's so cool. [00:47:00]

Mallory Mejias: Well, I'm curious, we talked about AI use cases. How do you see marketing evolving kind of in this greater AI landscape over the next? Well, I'd say year, but it's hard to it's hard to look out that for maybe the next six months to year.

Bill Macaitis: Yeah, I, it's amazing, because I can't think of a certain area of marketing that won't be transformed by AI, you know, and I'm thinking of all these different disciplines.

So like, if you're in demand gen, You know, if you're out doing a lot of programmatic buying, um, obviously having an AI tool that can go in there and make these decisions proactively, uh, whatever your core metric is, you know, return an ad spend, return, return investment, click through, whatever it is, right?

Like I could see that just being an incredible, um, you know, companion to help you out with. Uh, if you're in content creation, we talked a lot about that. Like it's just so, easy and frictionless to create content now, or it's much easier than it has been in the past. Right. [00:48:00] Um, I think of like, you know, compliance with, uh, etro tone and, and, um, from a copywriting perspective, like when we were at Salesforce, we had a very, you know, in the marketing team, we were like, this is how we want our tone to be.

But you know, you have like 10, 000 people in the company, they're writing everywhere. Right. But now you could go, Hey, go through all of the content that's. accessible and rewrite it in our tone like that's amazing that's hugely powerful right Um, I think from a visual perspective You know, Mid Journey, you know, Sora, some of these tools that are coming out.

Just so powerful, right? A lot of the visuals I use for my, you know, my YouTube channel are coming from AI. Um, it's hard! It's one of those, like, I can't think of an area. And so, I mean, the best way I thought of it is I know a lot of people are worried about, like, What does it mean for my job, or this or that, or am I going to lose my job?

Is I don't think like anyone that I think it's going to break down to two people, right? The people that [00:49:00] embrace AI and go, Hey, how can I use this in my job and be more efficient and productive? They're the ones that are going to stay, get promoted, get like better career path. The ones that are like, Oh, I'm not listening to the AI, you know, I don't care.

Like whatever, it's a fad. It's going to go away. Those are the ones I'd be really nervous about. Right. Um, cause I just think. You know, I can think of a thousand use cases in marketing and the problem is I think people that start to learn about AI, no matter what field you're in, problem or opportunity, right, they can also think of all the use cases of how to use it.

Um, so it's going to be a crazy couple years, right? Uh, I, I don't know what's going to happen. You know, I don't have a wizard wand and can predict the future, but I do know like these, these tools are very, very helpful.

Amith Nagarajan: Well, people ask me when I speak on AI all the time, what's going to happen to their jobs.

And, you know, my answer is very simple. It's that you, as an individual, are very unlikely to be replaced by AI itself. But you are very likely to be replaced by somebody who knows how to use AI really well. There you go. [00:50:00] And I think it's, it's, it just is what it is. You know, it's kind of like, you know how to use a computer.

And it's just part of life. And, uh, we may like it, we hate it, but it's, it's our reality.

Bill Macaitis: I think the good news is, anyone that's listening to this, like, you've taken the first step, right? Like, you're listening to this, like, you're being exposed, it's, it's becoming less formidable for you, it's like, less of a, you know, abstract concept that you've never actually used, so, you know, you're absolutely taking the right step.

Amith Nagarajan: Many of the fears that I hear also are from people who haven't yet taken that step, and that's usually my answer as well, is get started, start learning it, and you will quickly find that it is, first of all, it's not insurmountable, and many of the fears are misplaced. There are some very strong and legitimate fears with AI at kind of a macro scale in terms of what happens to society, what happens to people.

I or bad actors with all those big questions. But as an individual and professional role, um, you know, it's, it's pretty much been this, uh, so

Bill Macaitis: yeah, I, I'm still, I'm, I'm an optimist at heart and I try to be a [00:51:00] historian at heart. And I think most technology. Usually, a lot of times, it gets demonized right when it comes out, and you hear some of the stories of like, when the first automobile came out, and they forced it, like, they had laws where you couldn't go more than, faster than a horse, or, you know, you had to take breaks, all these crazy weird things of like, you know, how the automobile was going to be the death of society, and so, I like to hope that, hey, I think this will be, um, You know, consistent where, hey, it'll be a powerful technology that will transform humanity, mostly in a good way, potentially some bad things with any technology, but, um, you know, it's gonna be change agents and, you know, just, just be aware of it and stay on top of it.

And I think you're gonna do great.

Amith Nagarajan: There probably was a Horse Breeders Association behind that law about cars not going faster than horses while we were in Congress. In fact, Mallory, we should use Jax EPT to research that and see if we can dig it up. It probably is.

Bill Macaitis: Someone's doing it in real time right now.

They're typing it in. There's a great use case example. [00:52:00] Ugh, they

Mallory Mejias: should have used a freemium model. Well, Bill, thank you so much for joining us today. Thank you for bringing these SAS lessons to the association space. Where can listeners find more about you? You mentioned this YouTube channel. Can you give us any helpful links?

Bill Macaitis: Sassimo pro. That's the one, uh, you can find me in all social channels. Uh, like I said, you're probably, by the time this goes out, you, you might be getting the first bits of content that'll be coming out there, but Sassimo pro. The other way is if you just want to reach out to me individually, my name is Bill Masaitis.

Um, you can, uh, reach me on LinkedIn. That's probably the easiest way to, uh, to reach out to me.

Mallory Mejias: Thank you so much, Bill.

Bill Macaitis: No worries. Thank you so much for having me guys. I have really fun conversation. Awesome. Thanks Bill.

Mallory Mejias
Post by Mallory Mejias
May 30, 2024
Mallory Mejias is the Manager at Sidecar, and she's passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space. Mallory co-hosts and produces the Sidecar Sync podcast, where she delves into the latest trends in AI and technology, translating them into actionable insights.