Sidecar Sync

AI Marketing Strategies, PLG Insights, and the Future of User Engagement with Bill Macaitis | 32

• Amith Nagarajan and Mallory Mejias • Episode 32

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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.

🔗 Connect with Bill Macaitis on LinkedIn:
https://www.linkedin.com/in/bmacaitis/

Chapters:

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

This episode is brought to you by Sidecar's AI Learning Hub 🔗 https://sidecarglobal.com/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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Amith Nagarajan is the Chairman of Blue Cypress 🔗 https://BlueCypress.io, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the g

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Amith Nagarajan is the Chairman of Blue Cypress 🔗 https://BlueCypress.io, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the good fortune of nearly three decades of success as an entrepreneur and enjoys helping others in their journey.

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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.

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Speaker 1:

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.

Speaker 2:

Welcome to Sidecar Sync, your weekly dose of innovation. If you're looking for the latest news, insights and developments in the association world, especially those driven by artificial intelligence, you're in the right place. We cut through the noise to bring you the most relevant updates, with a keen focus on how AI and other emerging technologies are shaping the future. No fluff, just facts and informed discussions. I'm Amit Nagarajan, chairman of Blue Cypress, and I'm your host.

Speaker 3:

Hello everyone and welcome back to another episode of the Sidecar Sync. My name is Mallory Mejiaz and I'm one of your co-hosts, along with Amit Nagarajan, and I run Sidecar. Today, we have an interview lined up for you with Bill Masaitis. Bill is an advisor and board member guiding aspiring unicorns and decacorns. He works with companies to build out capital-efficient-to-market strategies and world class teams. Over his 20-year career, bill has achieved five successful exits and powered growth at three of the fastest ever growing companies Slack, where he worked as CRO and CMO. Zendesk, where he worked as CMO, and Salesforce, where he was SVP of marketing. We have a great conversation lined up for you today, where we explore the idea of more pain equaling more opportunity. We, of course, talk about product-led growth, or PLG, and how it can apply to associations. We cover freemium models and the pricing strategy behind them and, of course, when you have someone like Bill on the podcast, we talked about marketing AI use cases as well. Stay tuned for an exciting conversation after a quick word from our sponsor.

Speaker 3:

Today's sponsor is Sidecar's AI Learning Hub. The AI Learning Hub is your go-to place to sharpen your AI skills and ensure you're keeping up with the latest in the AI space when you purchase access to the AI Learning Hub, you get a library of on-demand AI lessons that are regularly updated to reflect what's new and the latest in the AI space. You also get access to live weekly office hours with AI experts and, finally, you get to join a community of fellow AI enthusiasts who are just as excited about learning about this emerging technology as you are. You can purchase 12-month access to the AI Learning Hub for $399. And if you want to get more information on that, you can go to SidecarGlobalcom. Slash hub 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?

Speaker 1:

Well, first off, thanks for having me, mallory, thanks for having me, amit, 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 nerd in sixth grade in the back that was reading Wall Street Journal, forbes and Fortune, so I've always had a huge passion for this. You know, I did entrepreneurship club, like in high school, and have always upended 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 Endesign Slack. So it's been an honor. I've always loved online marketing. I've always loved more innovative go-to-market models with SaaS and AI, so I was super excited when you guys reached out to talk today.

Speaker 3:

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.

Speaker 2:

I was right there with Bill doing that and yeah, I love that. You both know, so very impressive I was right there with Bill doing that. And yeah, it's in that group. And, bill, it's great to see you. It's been a while. Thanks so much for being here.

Speaker 1:

Oh yeah, Great pleasure.

Speaker 3:

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.

Speaker 1:

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. 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 Like these older spaces, these older industries have the most pain in them because they maybe they're not sexy Like I.

Speaker 1:

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.

Speaker 1:

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 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 about it, and so I'm like, oh, there's a lot of pain there, right. And so you know, for me that's been a cool kind of guiding compass that's helped me out.

Speaker 2:

That makes a lot of sense.

Speaker 2:

You know 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 group 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 your example of Slack makes a ton of sense. There's an inefficiency or something that's just troubling a lot of people and associations all over. 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 them to think about the products, services 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 to change rapidly and there's new opportunities. There'll be new pains and there'll also be opportunities to solve for pains that were previously unsolvable because of these technologies.

Speaker 1:

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 were 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. 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, and if you don't solve that pain, someone else usually will come around and do it for you.

Speaker 3:

Bill, I would call you maybe you would call yourself this as well a master of product-led growth, especially with 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?

Speaker 1:

Yeah, I'm definitely a nerd with PLG. I have two favorite acronyms in my life 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. So PLG, or product-led growth you'll hear a lot of different definitions. 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 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 and some people go like, oh, they'll create all this amazing stuff, but they'll put it all on their website or their blog and we'd like to think everyone's going there. But we know like three or five percent of your people are going there. Right, but how do you like, infuse all that good marketing and into the product? Right, 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 a 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, 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 like a you know, terrible experience there.

Speaker 1:

The other big tendency we have in PLG is you want to have 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 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, 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. 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 and put a fun little image in there. People want to have fun with it and so product-like growth is all about.

Speaker 1:

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 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. It's hard to use, so you have to go to a customer success person. It's just a different way of kind of building more modern AI and SaaS tools.

Speaker 2:

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. So it kind of adds richness to the experience beyond just the enjoyment. It's, I think, a really powerful modality and I think associations generally I would say it's a generalization that 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 association of accountants, 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? I think there's probably lots of ways to do something in kind of that fun realm.

Speaker 1:

I think there's probably lots of ways to do that, but I'd love to hear your reaction to that question. Yeah, no, it's a great question and 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. 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 know style, you're going to, you're going to use some different metrics, right? So two really big metrics we use. That Slack was daily active users, so that is literally just how many people come to your software every day. And that's how many people are coming to your association, maybe the website, the resources you have. How many are coming every day, right? The other metric we used was net promoter score. So I mentioned earlier NPS. Simple question how likely are you to recommend to a friend or colleague score scale of one 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 do 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, because you know, to your question like, how do you make it a little more fun?

Speaker 1:

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. You know, when people visit you more and they like you more, in general, I found all the substream revenue metrics tend to work out better. They tend to pay more for you, they tend to renew more, they tend to attrit 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 they're recommending. You know, all your other metrics tend to do very well and that's a good. Those are good input metrics.

Speaker 1:

I think, like a lot of times, revenue metrics are output metrics. 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. You know, maybe have some more real, authentic conversations. Or just think about, like, the content that get with people that they would enjoy more. Right, that maybe they're going to laugh a little bit. I think those are all easy ways to kind of get some some big wins there.

Speaker 2:

I think you know one small idea might 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 navigate people to it, the way you kind of help them approach that content could perhaps take a little bit lighter tone, a different style. 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 particular person and say an environment like a learning management system. Let's say we're in associations that bring professional education. 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 characteristics, give Bill a little bit different experience than perhaps somebody else who's very serious and different personality style. Of course, ai exactly what AI is so good at now. 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 the environment of a product is storytelling.

Speaker 2:

We know that 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. Yet we don't do that in business communications. We don't tell stories live. And once again we have, with language models, particularly as they continue to relentlessly improve, opportunities to potentially do a form of translation. And when we talk about translation, people immediately their brain goes to like English to Spanish, which is amazing. That's unbelievably exciting. What about translating a piece of content into a vibrant story and then delivering that story and seeing who can deliver the same educational insights, but through storytelling? What's your reaction to that kind of approach? I'm just curious.

Speaker 1:

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 are 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 many people tap into is the tone and voice, 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 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. You know, 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.

Speaker 1:

You know the capabilities are just incredible and you know 4.0 and Gemini and there's just there's so much new advances. And you know, 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, yeah, there's so much opportunity there and I love the personalization, I love the tone, I love the refactoring of existing content. Um, there's tons and tons of opportunities for for associations right now.

Speaker 2:

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 they're related to it and you think about the amount of content a CPA society might have that could be relevant to the broader audience. Going right back to what you just said, there's opportunities for repurposing, refactoring, different kinds of storytelling, and a lot of associations 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 potentially considering these adjacencies.

Speaker 1:

Yeah, I mean there's so many great adjacent markets. You know I'm always surprised with 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 bring to life the stories of your customers right, like when you hear from 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 which is 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 I think it's I think it's critical for an association to think about that.

Speaker 3:

I'm big on the stories, I will say that, just as 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?

Speaker 1:

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 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.

Speaker 1:

But yeah, I think memberships are a 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 and science to how you price and package these things. So I tend to be a big believer in the freemium model. That's usually a key tenant 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 usually get, you know, usually free to paid as like one to 5 percent 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, people start to experience a lot of value and then you can think about what are your triggers to upgrade differently.

Speaker 1:

So, for instance, a lot of people use features to differentiate their plans. You know, on plan A, you get 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 and then your access gets cut off. But they'll say, hey, you get a free plan, you get to access almost all of our features, but we're going to put some thresholds in right. So, for instance, for OpenAI, for instance, you could 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 that, you need to upgrade.

Speaker 1:

And so I think those concepts are really powerful because, at the end of the day, so anyone that's in an association, anyone that's marketing an association, you generally have a directive right you have to go out and 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 we had like a million free users.

Speaker 1:

I didn't look as we had a million free users.

Speaker 1:

I looked as we had a million free marketers right that were out there talking about 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 saying like a free user is a bad thing.

Speaker 1:

It's actually like it's a marketing cost, if you will and that marketing cost a lot of times is cheaper than the alternative forms of demand gen or paid media that you're out and find new members. 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 because I want to have more unlimited access to all this. Right, it's a very different sell than 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.

Speaker 2:

I think those are on the pretty much bullseye for the association market. 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 not so much on a defined customer group that they've oftentimes had 80-90% market share with already, but to think about the broader context of where they can provide utility and to do exactly what you're saying to make some content available, to open the garden, to bring people in, to share some of those resources, which, of course, advances their purpose. 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 downstream where you can offer higher value for higher investments. So love the model. Investments, so love the model.

Speaker 2:

I think that one thing that I would say is, I think, kind of interesting for associations now to consider with. 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 it's behind a paywall. You have to register. It's still free with that style of free, new, but 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 or other search engines you know, don't even have to send the traffic your way? What are your thoughts on that? Just, it's on topic, but a little bit to the side of the experience.

Speaker 2:

What do you feel about that?

Speaker 1:

Man, it's the million dollar question, right, that every content creator is thinking about, is worried about. You know, is my content just going to be put out there 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 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 Reddit and some other services where they're trying to get the content. So, hey, maybe that's a future revenue stream for you.

Speaker 1:

I don't know, I mean, at the end of the 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 would my viewer like? Right, and if I can provide utility and value to them, then that's generally a good thing, right, and so I wouldn't, I wouldn't let it completely drive you, you know, to not putting it out there, right, if you will. I just think, at the end of the day, 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.

Speaker 2:

That makes a lot of sense. I think lowering friction for the users, creating value, making it easier, is super important To the point you made earlier. Associations do often have something quite unique. They typically what I would go so far as to say often have the best content in their field or their sub-profession 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 Even their members who are paying. There's a lot of backflips that are being done to just navigate websites, and 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.

Speaker 2:

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 at not not a scalable solution. But you can do that with ai, where you just publish the summaries or publish some component, oh yeah there's.

Speaker 1:

I mean, I'm a huge believer in content marketing, so anyone that's part of association, that's creating content like hey, love you. I've. I've been there like slack, zenda, 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 and 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, and AI has been hugely helpful throughout that entire process right For me as a content creator.

Speaker 1:

So, yeah, like 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 the explosion of all the different social channels. So I think, in a great way, like all the associations, 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 AI is like a huge part of it can be a great asset to you to make that process so much easier.

Speaker 2:

The other question I wanted to ask you is when you think about your funnel strategy, going from free to paid a lot of associations it's kind of like going from hanging out at the Ahuani Hotel at the base of Yosemite Valley enjoying a cocktail to scaling the face of El Capitan Right. It's like a straight vertical leap to something very pleasurable and enjoyable to like. Oh crap, I'm not going to do that, right. What about you know some kind of a tripwire offer, something that's just a very small little purchase. I'll give you one example of what we do.

Speaker 2:

Sidecar, effectively, is like an association. We don't have members, but we have the concept of very, very similar engagement. 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. Then we have this $25 thing which is this mini course. We call our prompt engineering boot camp or mini course setting, so we call it right now, and the idea is we also have a $400 learning hub, which is a much bigger investment in learning, and so what we're trying to do is get people to convert from one to the other to the next. What are your thoughts on some kind of a little bitty but paid offering that precedes membership, maybe to get people warmed up to the other? To the next. 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?

Speaker 1:

Yeah, I love the idea of having you know ladders, easy steps that you can make right. 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. Those are all just big friction moments, right. And what you tend to see with those is just very low conversions, right.

Speaker 1:

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 upgrade drivers. But even having you know some different plans, some easier plans, maybe some one-offs, a big part of you know my business is how do you cross-sell, cross-pollinate users that 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, 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 just, you go from nothing to 100, right, it's like you have this giant cliff and you know zero to 100. 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.

Speaker 1:

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. 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, 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, 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, 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 problem sets that we're going through. We can be inspired on their solutions.

Speaker 3:

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?

Speaker 1:

Yeah, I love those multiples. I've generally gone to 2x, 3x, 3x. So if you have multiple tiers, I like a free tier and then a 2X from the first page, the second page and then a 3X from the next one. There Am I getting that right? And then one more 3X.

Speaker 1:

Essentially what I found if you want to distill it down to just easy to understand language is that your SMB market, so the people that are in SMBs are the most price sensitive, right, and they are ones that are like going to fight you on a dollar increase in price, right. The further you up market, the least price sensitive they are, right, and so you can get you have much higher increases on the high end. So you know when I would tend to look at it again. 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 black. 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 it as hey again, that was our marketing engine. So the free segment and the SMB segment, like the first, the free plan and the really low, the 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 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.

Speaker 1:

The problem is, if you just skip straight to the higher up and, by the way, I see this all the time I, you know, I currently serve as an advisor 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, but no one knows us Right.

Speaker 1:

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.

Speaker 1:

So that's a, that's a 0.0000, right, 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, users that normally wouldn't sign up for you because they're price sensitive.

Speaker 1:

So if you have a, you know, an intro price that is relatively, you know, reasonable, you're going to 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, 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 you're doing peer user, you know UB, peer 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 get, you pay more. But those concepts are really important, right.

Speaker 2:

Like have. I recommend have multiple tiers, have a free tier. That first tier should be just, you know, not that much at all a little bit, and then 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, et cetera. That didn't really affect the users, the end users, that much, but they provide enterprise level value. There's value at the board level, even though the individual wouldn't necessarily discern the difference.

Speaker 1:

Can you talk a little bit about that? First off, I mean I'm so happy you remembered that that is like my advanced pricing and packaging course and you just got an A on it. So well done there. Yeah, so this is. I mean, I love geeking out on this stuff and I would say this is a really advanced level pricing and packaging strategy, which is there's two ways to get people to upgrade. I talked about one, which is the threshold model, right? So you basically have a fee at a user feature level. You want all the features that your users can access at any level, but you'll put some on a couple of. You put thresholds right. You can only use it X amount of times per month, per year, whatever it is.

Speaker 1:

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. You know provisioning deprovisioning SSO compliance exports legal. Consolidated billing, dedicated customer success manager, 99.999% SLA uptime Stuff. That just like enterprises have to have right.

Speaker 1:

Like if you are 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 has? No, they're not. But what that means is now 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. And again, that fits in with that POG 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.

Speaker 2:

So, bill, I think you'll like this. Not only did I remember what you taught us at Rasa in those early days, but we actually wrote about you, not specifically by name, but we wrote about that strategy in chapter six of the book that we used on AI for Association.

Speaker 1:

Awesome.

Speaker 2:

I love it. 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 market. I wanted to contextualize this for a minute with an idea from that chapter of the book and get your two cents and try to translate a little bit of the sass 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 structure, even in the bylaws of the organization, where they can't 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. But the idea might be to have some premium product beyond membership that might encapsulate some of these higher-end things. And coming back to the teacher example, there's actually some teacher associations in our ecosystem that are rolling out AI bots, which are much like ChatGPT, where that's based on the world's content and not the 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 of the association. Now, it's a good reason to stay there. It's a good reason to join If I am the school district and I look at that and I say that's awesome.

Speaker 2:

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 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 bot's thinking and the recommendations and the crafting of the lesson plans. That would be kind of like the corporate standards, the corporate governance.

Speaker 2:

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 teachers association, that can incorporate that school district level or even school level content and it overrode, essentially, if there was conflict, the teachers associations based 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 and our thesis was essentially that's dramatically greater value and therefore potentially 10x, 20x, 50x, whatever the number is increase in value and therefore revenue opportunity. What's your reaction? I think there's a little bit of a parallel to that between how Slack would sell something that had an enterprise-grade feature. What's your reaction?

Speaker 1:

Yeah, I think that's, at the end of the day, day. 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, you know, putting together these lessons plans in a way that is accessible and is compliance and has everything else. So they have pain points. Right, and you're using more localized LMs 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.

Speaker 1:

And wherever there's value, you know, there's opportunity right to monetize that and to price it and to help people out.

Speaker 1:

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 just be like, hey, I'm going to translate all my lesson plans into you know 28 different languages, right, but now you can do that in five seconds, right, 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, is like, wow, ai, this is scary stuff right, like what's going to happen? What does it mean for me, what does it mean for the job, what does it mean for this industry? But there's so many use cases that are coming out and a lot of them are really good and valuable and I think, just you know, keeping your ears open and being inspired by cross industries and how they're using and think about how you can use it for your particular spaces is very powerful.

Speaker 3:

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.

Speaker 1:

Yeah, right now I am knee deep. I'm creating my own YouTube channel. It'll be called Sassimo Pro Might be out by the time this comes out here and so I'm creating just a lot of content myself and, as we've shown earlier, I've got some different video angles here for the studio, which is a little bit crazy, but a lot of what I use is, hey, going through that process. So, choosing that name, sassimo Pro. I've looked through 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. I use AI there. You know it's unlimited. The thumbnail titles you know that I come up with. 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 um AI tools and asking those questions, right, um, and you know it's, it's fun. So I have um, sassy Mo Pro.

Speaker 1:

We have a sloth. That's our 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.

Speaker 1:

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 Zs 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. I'm like, hey, what that style of speaking, and it will come up with five different variations of that, and then I'll put those into my video. So I just think it's one of those things that is 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, you're tinkering, and then here's someone else that uses it in a really cool way, either professionally or personally.

Speaker 2:

But for me, those are some of the use cases that are at least top of mind for me right now, bill if you're talking to someone who hasn't used AI much and is overwhelmed by it, what's your advice for them to help them get rolling?

Speaker 1:

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.

Speaker 1:

I mean, I'm always saying like, hey, really easy one, 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. 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 work type stuff, I'm really trying to ask myself where could I, where could I eliminate some of this? So, in other words, like right now, like I am 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 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?

Speaker 1:

Right, like I remember one task. I was going through all these videos and I was like I had to delete one camera angle that didn't work, go back and forth, and it took me like an hour. Right, it was a very repetitive task and 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 yeah, I'd say start small. You know, listen to some stuff. It's intimidating at first, but the more you dip your toes in, 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. Oh, I'm swimming. This is great. Right, it's a it's. It's not that big of a deal.

Speaker 3:

Have you tried out the tool munch bill?

Speaker 1:

No, I don't think so. What is this? Well, those are Opus Clips. I have, yes, munch, I haven't.

Speaker 3:

Munch is, I think, similar to Opus Clips. Actually, 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.

Speaker 1:

So I mean I'm learning stuff on this one. I love it, Go for it.

Speaker 3:

I know. So the first time I heard this was actually from Erica, who's the COO of Rasa, who you might know, who you probably know, but she, 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.

Speaker 1:

That's a fantastic one. That's so cool.

Speaker 3:

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 look out that far. Maybe the next six months to a year?

Speaker 1:

Yeah, 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, obviously having an AI tool that can go in there and make these decisions proactively. 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 companion to help you out with. If you're in content creation we talked a lot about that Like it is so easy and frictionless to create content now, or it's much easier than it has been in the past. Right, I think of, like you know, compliance with Ectro Tone and, 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 go. You have like 10,000 people in the company they're writing everywhere, right, but now you 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, I think, from a visual perspective. You know MidJourney, 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.

Speaker 1:

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 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.

Speaker 1:

The ones that are like, oh, I'm not listening to 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, because 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.

Speaker 2:

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 is that you, as an individual, are very unlikely to be replaced by AI itself. But you are very likely to be replaced by AI itself, but you are very likely to be replaced by somebody who knows how to use AI really well. And I think it's. It's just what is what it is. You know, it's kind of like do you know how to use a computer? And it's just part of life and we may like to indicate it, but it's, it's our reality.

Speaker 1:

And 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 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.

Speaker 2:

Many of the fears that I hear, also 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 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, kind of the macro scale in terms of what happens to society, what happens if there's bad AI or bad actors with AI, all those big questions. But as an individual in a professional role, it's pretty much been just so.

Speaker 1:

I'm an optimist at heart and I try to be a historian at heart and I think most technology usually a lot of times 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. You know how the automobile is going to be the death of society and so I like to hope that, hey, I think this will be, you know, consistent, where it will be a powerful technology that will transform humanity, mostly in a good way. Potentially some bad things with any technology, but you know it's going to be change agents and you know, just be aware of it and stay on top of it, and I think you're going to do great there, probably was a horse breeders association behind that law about cars not going faster.

Speaker 2:

Now that we should use Jax EPT to research that.

Speaker 1:

Someone's doing it in real time. Right now they're typing it in. There's a great use case example.

Speaker 3:

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

Speaker 1:

listeners find more about you. You mentioned this YouTube channel. Can you give us any helpful links? Sas CMO pro, that's the one. Uh, you can find me in all social channels. Uh, like I said you, probably by the time this goes out, you you might be getting the first bits of content that'll be coming out there. But SAS CMO pro the other ways. 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 reach out to me.

Speaker 3:

Thank you so much, Bill.

Speaker 1:

No worries, thank you so much for having me, guys.

Speaker 2:

I had a really fun conversation. Thanks for tuning into Sidecar Sync this week. Looking to dive deeper? Download your free copy of our new book Ascend Unlocking the Power of AI for Associations at ascendbookorg. It's packed with insights to power your association's journey with AI. And remember, sidecar is here with more resources, from webinars to boot camps, to help you stay ahead in the association world. We'll catch you in the next episode. Until then, keep learning, keep growing and keep disrupting.