How Early Startups Can Rapidly Test Messaging & Dial In ICPs| Larson Stair of StairStep Strategies

I have an idea of the problems that customers are experiencing. I need to speak to that, but I need to speak to it in a variety of different ways. It could be the same exact problem, but there's a lot of different ways that you can discuss that problem. It could be written blog posts. It could be facts about that specific problem or impacts of that problem. So you never really know how a message is going to resonate with somebody. And so I think about how can I generate a lot of different ideas about one singular topic to see what is going to resonate in a way that I frame it with people out there. what is the right presentation of that? So is that written form? Is it video form? Is it a static image? And it could be of the exact same message. I mean, everyone wants to build this billion dollar organization that has, is a platform focus that's catered to many different industries and many different personas. But if you try to hit that right out the gates, you're really gonna be a mile wide and an inch deep. You're not gonna... get the traction and enough learnings deeply enough into each of those segments. And so, you know, Techstars did a really good job of this with us as they said, okay, when you think about your ideal customer profile, the exercise is to narrow it enough to where who do you think you can close 100% of the time? You're really thinking deeply about criteria that could be happening. It's like, yeah, we want to go after small private practices, but think even more deeply about that. I mean, maybe they're hiring in a specific category. And the exercise is to actually narrow your ICP to a point where you're really confident that they have the problem to your solution and really trying to go out and dominate that one very narrow niche. And once you really get a good foothold there, you've learned a lot, but you can start to begin to expand more methodically. But the trick is to not do that too quickly because you're kind of sacrificing key learnings that you could have as you go deeper into one particular segment. I was the first one, as CEO of the company, to admit failure. I called myself out. Like, that didn't work that well. This part was maybe okay, but this was not good enough. Like, we need to change this. And by self-admitting your own failures, it opens up the door for others to do the same thing. Like, this is okay. And, like, it doesn't make me a bad person. It doesn't make me bad at my job. Like, one piece is not reflective of the holistic here. And so, in a similar kind of retrospective kind of framework, they call it the Weekly 808. It was held at... 8.08 p.m. every Thursday where it was you reflected on like key learnings from the week, the win of the week, in the ditch award. So if you really messed up, you have to say it yourself. And if you get the in the ditch award of the week, you win the like award of the week. Welcome to the Tech Marketing Masters podcast, where we interview CMOs and VPs of marketing and tech to give you an inside look at what other tech marketing execs are up to. what's working in marketing these days what you can try with your team and how to level up your marketing game i'm your host lee cooper co-founder and ceo of cooper an seo marketing agency that helps tech companies grow their organic search traffic i'm joined by larson stair founder and ceo of stair step strategies which helps seed stage startups build a revenue engine that unlocks a new phase of growth today we explore a lot of really great insights like How to quickly test new messaging with content marketing and how to create a process of rapid experimentation there. How early stage startups should zero in on their first ICP and the importance of crafting messaging unique to each additional persona. How marketing and sales can share insights into which messaging is resonating with their audiences while maintaining at least some brand consistency across departments. How Techstars weekly 808 retrospectives can help your team create a culture of honest self-accountability and experimentation, and their in-the-ditch award can immunize your people from a paralyzing fear of failure. How your team can build a strong habit of creating content early on and then get into the habit of measuring the effectiveness of that messaging. And the 80-20 rule to use when writing your content that makes sure your content resonates with your audience more than it promotes yourself. If you're interested in any of these things, then you won't want to miss this episode. Let's welcome Larson to the show. Larson, great to have you on the show. Yeah, thanks, Lee. Appreciate you having me here today. Yeah, I think we were talking a little bit earlier, but maybe if you could give a quick introduction for the people who are hearing you for the first time and sort of where you come from, you know, maybe some of the stuff you've worked on and kind of how you got into marketing. Yeah, for sure. Well, for those who don't know me, my name is Larson Stare. Background, I was born and raised in Wisconsin, but I'm based out of Colorado here. Moved out west. you know about 10 years ago uh background was really in medical uh and wanted to become a doctor but decided after i had medical school applications in that i wanted to become an entrepreneur and i wanted to start a company and so it took me about 10 years to get there but that kind of led me to denver and to my first startup called demo flow where i was the ceo of that company demo flow or gondola so went through a bit of a name change But I was CEO of that company. My background really is on sales, marketing, and that's kind of the sphere in which my influence was within that company there. Since selling that company, I started a consulting company called StairStep Strategies, where I work with early stage, seed stage companies to build their sales motions and help with fundraising. So that's kind of what I've been doing since that company. Yeah, that sounds good. I'm curious really quickly, just like a little bit about what. demo flow slash gondola did you know product market all that kind of thing i'm just curious yeah yeah of course so demo flow was a solution a sales enablement solution that helped to create consistency within product demonstrations so if i'm presenting to you And if you're the CMO of a larger company, by contrast to maybe a CEO of a small SMB company, those are different types of presentations that need to get completed. And ultimately, the company wants consistency in that narrative. And so that's what our solution brought to the table, was making it easy for anyone at a company to be running a product demonstration in a way that is really in compliance with what their team wants them to be presenting. And that shifted a bit. throughout the three and a half years we were running it full time to a solution called Gondola, where we became a little bit more play agnostic or call agnostic, if you will. So it wasn't just a demo solution. It became a solution that you can utilize on discovery calls, running through proposals and helping to get your sales team to follow the playbooks that you want them to be following, asking the right questions, gathering the right information and presenting in the right separate way. Yeah, that makes a lot of sense. I can see a need for that one. It's like on one hand, good salespeople are in some cases like good cowboys who can kind of like find all sorts of weird angles. But on the other hand, sometimes they find some truly creative angles that the company is wasn't expecting. Yeah, for sure. For sure. Absolutely. And, you know, when it comes to, you know, you really want your more senior sales reps to be given the kind of guardrails, but also some room to be creative in those senses. Exactly like you're saying. the more junior reps we want to get them up to speed as fast as possible so we maybe don't need them to be cowboying quite as much but we want them to kind of follow the guard rails a little bit more stringently than maybe somebody who's in a more senior position um so that's kind of ultimately what we allowed them to do yeah that makes a lot of sense and then since then you moved on to to stair step and you're saying that kind of helps seed stage companies build sales motions and that kind of thing i'm curious if you have like a maybe like a really quick story on maybe one company you've worked with or something like that, just to sort of help people know what that looks like. Yeah, for sure. Really a lot of the work that I start with begins in like the initial calls and sales calls that a startup founder may have with their audience. So a lot of work I do begins as early in the funnel as possible. So that could be identifying your ideal customer profile, who are the right titles to be reaching out to to generate leads. uh but really the where a lot of founders make mistakes is in that first discussion where they think hey i've spent years building this product and it's my baby and just wait till i show you it's going to be incredible you're going to love it and ultimately what really matters is what is going on in that prospect's life the how they operate today as a business where there's friction in that process and if you can help solve that friction that is ultimately the right way to be going about doing this. So not leading with your product, following with your product, leading with right questions. And I'd say almost every single founder I work with struggles with that exact same thing. So I could tell you countless stories about that specifically, but that's really where a lot of my work begins as that kind of early stage sales cycle begins. Yeah, yeah, I can definitely see that because so many so many entrepreneurs and especially at that stage. if someone's a little bit insulated, they're very like focused on the product, but they haven't focused enough on the problem that the product solves, then they're walking into a fun conversation there. But on the other hand, it's also like really, really strategic for people to be getting the feedback from, you know, potential customers or actual customers and be like, what is the problem here? How much is our product actually solving that? Like, where's the connection? You know, to me, it's one of those things where the faster you can get a founder, to that kind of feedback the faster they get to honestly a better like product market fit as well as being able to scale that later on yeah because ultimately i mean if you're not solving a pain then what are we really doing here you're not even really building a business that is sustainable over time and so you really need to be focused on the problems that people are going through less on your your features or your your specific product but more on on them which is a bit counterintuitive in the early days Yeah, that makes a lot of sense. And I think some of that is it also like once people get into that feedback loop, you know, they're kind of like they're talking to real customers, they're understanding the problem first and then, you know, the product second in a way that sort of helps them iterate towards finding the right messaging. And I think that's something that you and I were talking about earlier was you were talking about how you had done some things at Gondola and you were using content in various ways. And, you know, early on, there were there were some problems maybe with the way that you're doing content but you sort of found that there was a way to use content to iterate on messaging with with a higher level of agility so i'm just curious like in those early days like how how are you approaching content at first and and that sort of thing yeah i mean in the early days um i really viewed it as exactly that as a way to test out messaging and so to begin that i was like okay i have an idea of the problems that customers are experiencing I need to speak to that, but I need to speak to it in a variety of different ways. It could be the same exact problem like, you know, sales reps aren't doing a good job of articulating the value of each feature behind their product demonstrations. That's a problem, right? Why is that a problem? But there's a lot of different ways that you can discuss that problem. It could be written blog posts. It could be, you know, facts about that specific problem or impacts of that problem. So you never really know how a message is going to resonate with somebody. And so I think about how can I generate a lot of different ideas about one singular topic to see what is going to resonate in a way that I frame it with people out there? What is the right presentation of that? So is that written form? Is it video form? Is it a static image? And it could be of the exact same message, but people learn in different ways. And so I viewed it as both a messaging exercise on How many different ways can I articulate solutions to a problem or walk through that problem, but also in a presentation standpoint? So what is the right format by way which people want to be digesting this information? And so that helped us really, you know, we put out a lot of different styles there where it wasn't like a brand guideline we were trying to follow, maybe some coloring or such. But that, you know, by taking these, you know, getting a lot of lines out there, we can get feedback from the market. sometimes called vanity metrics, likes, shares, comments, impressions, and then that could give us clues as to, oh, maybe this is a better way that this might resonate with this audience, which could go on and change copy on your website, so on and so forth. Yeah, yeah, that makes a lot of sense. I guess, is there any examples where you were trying out some messaging, like first time, you didn't know how it was gonna work out, and you're just thinking like, hey this is this is a point I want to make and like sort of how you you approached that you know what I mean yeah there was a specific point where um in the demo flow day so this is like 2020 and it was probably fall time frame uh it's about four years ago and we were adding additional functionality so our main target at demo flow were solutions engineers or you know kind of the demo experts of the sales ecosphere Typically, they partner with sales reps. And so we were bolting on an additional user into our platform. We had the more technical audience, which is sales engineer solutions consultants, but they partner with your account executives. And that's a whole different audience. Like, what do they care about by contrast? What their skills are? What do they care about in their day to day? All of that is different. Trying to put out different messaging about, are you collaborating effectively with this other party? Creating messaging that is around collaborative, working with your team, but also catered to that individual, which is a sales rep. So we did it incorrectly a lot in the beginning days, but you got to do it. I think you have to do stuff incorrectly a little bit at first, or maybe work through some of those failures to kind of get to a better way of messaging or ideas there. So that was a really. a challenging time to try to cater to two different audiences and i think in hindsight we probably didn't think deeply enough about each of those audiences we're probably a little bit too uh you know off the cuff so to speak um putting messaging out there um but you know we kind of hone that in a little bit with time as we really try to map out these different audiences what do they care about what are their main focuses and then you know create content based upon that yeah yeah i can see how that that's a tough one because like you know it's it's definitely a lot of startups they have this whole thing of like let's take over the world let's go after all these different personas and these different markets and we're gonna we're gonna nail down the small businesses and the medium businesses and we're gonna go enterprise you know it's uh it's all the same right it's all sales and yeah yeah sure not really yeah and so it's you know it's easy for people who are who are founders to kind of try and take over the world which is and on one hand it's great to have that ambition that drive but so commonly i feel like you got to nail one one good persona first and then like strategically expand from there and it sounds like you were kind of in that situation where you sort of had one one persona there you had another one and then you needed messaging for both as well as the collaboration between them it sounds like there were like a few difficulties in there and and you know teachable lessons if that makes sense for sure absolutely absolutely i mean i think one of the kind of primary things you know to your point around you know as startups you need to have an you know ambitious mindset and a big vision that you want to go after there's a bit of like it's a bit counterintuitive where i mean everyone wants to build this billion dollar organization that has is a platform focus that's catered to many different industries and many different personas but if you try to you know, hit that right out the gates, you're really going to be a mile wide and an inch deep. So it's really, you're not going to get the traction and enough learnings deeply enough into each of those segments. And so, you know, Techstars did a really good job of this with us as they said, okay, when you think about your ideal customer profile, the exercise is to narrow it enough to where who do you think you can close 100% of the time? And, you know, so. you're really thinking deeply about criteria that could be happening. It's like, yeah, we want to go after small private practices, but think even more deeply about that. I mean, maybe they're hiring in a specific category and the exercise is to actually narrow your ICP to a point where you're really confident that they have the problem to your solution and really trying to go out and dominate that one very narrow niche. and once you really get a good foothold there you've learned a lot but you can start to begin to expand more methodically but the trick is to not do that too quickly because you're you're kind of sacrificing key learnings that you could have um as you go deeper into one particular segment yeah yeah i think that's always one where i i see founders like they they make the mistake of going too wide too quickly then i i is too big for their for their uh their stomachs if you if you will um and it's really difficult to communicate the importance at least in my mind of just like how truly important it is to just nail one thing um and just like really have i like the way that you put it was like a persona that you can close a hundred percent of the time because i think that makes it very tangible you know it's just like these are the people that you would totally sell and it works and then from there can you expand one step out from there? Exactly right. It sounds like you were expanding into, if I understand correctly, solutions engineers and finding the messaging there. I'm just curious, what did that experimentation process look like? Yeah, I think, well, we started with the solutions engineers. That's where I worked. I was the demo expert in the enterprise space. for a company who worked at BirdEye previously. So I had a good sense of kind of what that persona looked like. And as we expand into account executives, we thought that same exact messaging would translate. But again, they're very different audiences. Like solutions engineers are technical by nature. They can kind of talk tech, but they can also have a sales conversation as well. Account executives are different. They tend to be, if it's worked in the past for them, they think it'll work for them into the future. They tend to be a little bit resistant to change at times. And so there was probably an element of change management that we didn't really take into account. We thought about that audience there. And what sales reps really want is they want to close more deals and they want to do it really fast and spend most of their time on closing activities. I think we tried to take an element of collaboration as our initial messaging, work better with your sales engineers, level up their game. That really wasn't what the top concerns were for a sales rep. That's not what they're really, really focused on. Yes, they want to collaborate effectively with that team, make sure those calls go well, but it's probably like in the top 10 of problems or requests like. they want to be they're spending too much time on lead gen they want to work more qualified deals they want to spend less time on admin work um so on and so forth and so we only learned these through putting stuff out there and realizing this isn't working this is not the right messaging here it's fallen flat on the content it's fallen flat in the pitches so i'd also mirror what we were putting out there from a content standpoint into a lot of my pitches and you know uh you know as many ceos do you get really good at articulating the same pitch over and over and over again in slightly different variations and so i take a lot of that uh revamped messaging into the pitches that i was doing just to continue that experimentation yeah that that is kind of interesting in some ways it's like there's the pitching you know verbally where you really get to see someone's reaction but then there's also sort of the content end which is sometimes a little bit more disconnected, but you can still sort of feel when it's not getting traction or when it is getting traction. I'm just curious, like at what point did you look at and you're like, this is not really resonating from a content perspective, you know? Yeah, I think, you know, I was probably, I had just kind of a bias towards action. So I would rather, as opposed to being told it's not working, I'd rather just try a lot of different stuff. you know not kind of rest to my laurels and be like oh i think that one got that one got 50 likes and a lot of impressions like let's do something similar again there i might file that one away for next month or next quarter to revamp that again but i also want to try some other strategies here like a lot of different stuff proactively not really reactively because i think especially when it comes to creating content it's a momentum game And it's hard to be disciplined because there's a lot of like activation energy that goes into recording content or writing a blog post. And what am I going to write or say? And the fear of, you know, what if it's not good? And so I was just really trying to have a bias towards let's just let's keep it going. Let's keep let's keep the pace up here and let's try a lot of different things. And then, you know, maybe, you know, next quarter, I'd say, OK, let's look at what. what really resonated with folks and how can we do a slightly different iteration of that kind of similar messaging there and then we revamp it again maybe different graphics there maybe a different kind of title but um that's a little bit about how we approach those pieces yeah so it sounds like a big you know bias towards you know let's make some movement let's just get it going for the sake of getting it going and then let it go out there for a little while look back on it you know at the it sounds like at the end of the quarter or something and then look back and say okay how much did it resonate from there and then how much does that inspire me to try something new going into you know the next quarter um is this something that worked and we should do more of it or like rework it do other formats or is it something where like it just died on on the algorithm um or something like that and you're like okay maybe we don't do that one again that sort of sound right yep exactly right Yeah, I'm curious when it comes to that, there's also like an element where you said that you're kind of like you're using the content end, you know, and I'm assuming stuff like LinkedIn and, you know, other places like that. And you're also using it in pitches, which is kind of interesting to me because, you know, as an SEO, I actually get a little bit insulated sometimes from the sales team. I very rarely talk to sales just, you know, for better or for worse, the SEO usually isn't in that conversation. um and it's one of those things where there there can be like a segmentation between the marketing and the sales especially later on you know for a lot of startups and there may not be the same consistency from like the the content that marketing is working on to the pitches that sales are are giving and there's like there may not be that feedback loop between sales people are seeing like this stuff resonates this doesn't content team sees these things resonating and not and they're not necessarily like talking as much i've seen that kind of happen i'm just curious if you have any like advice around that yeah well um in in my time running the company it was quite simple to create that collaboration because you're looking at the marketer and you're looking at you know the sales leader so to speak we had sales reps that worked for us we had you know one kind of more junior level marketer that helped so that collaboration was quite simple but i i do believe that this is like a cultural point as leadership starts at the top. So I believe that it shouldn't really fall on the sales reps to be communicating back to what's working and what's not. It's not really within their job. We want them to be closing deals and stay focused on working qualified opportunities. I think it starts at the top. So how are managers, directors, VPs collaborating with managers, directors, and VPs in each different department? And what is the working cadence behind okay, I sat, you know, all of our managers sat in on calls over the past month and we had an internal collaboration on sales. We need to meet monthly or quarterly with marketing, see what's coming out next and any ideation that can happen on, okay, is this right, wrong? What are we hearing from the marketplace? Unfortunately, that is a piece I think is quite missed at times between those two departments because, hey, you know, At times they could be at odds, but we should really be as allies as much as possible and kind of create this space to deliver feedback and set our egos aside and be like, hey, I don't know if that's going to work or we try this, it did work, let's try to double down on it. Yes, it's very much a leadership and then creating that culture, moving down so that the departments are coordinating. I guess if anyone out there is struggling with that now, what would you tell them on how to start moving towards better coordination? Yeah, well, retros can be retrospectives can be a huge help when it comes to this. And we were really disciplined upon this where we do it on a monthly and quarterly cadence. There's a lot of different ways to do retros, but keep doing, start doing, stop doing is one way where it kind of forces you into a mode of reflection on what has been working here. Where are maybe from the sales, where are our best? where is the best place for us to start in terms of a title that helps get us as an entry point into an organization. So yeah, really just simply put, but the other importance behind this is letting data be a really guiding light. So bringing that to the forefront and let's make sure we have all our tracking in place for the content that's going out there and let's try to analyze on a monthly or quarterly basis. what really worked here what did not work but then you get the sales element too that helps you bring in some of that collaboration so we did retros all the time uh whether it was on something like a mural board uh digitally or something in person just sticky notes um and a lot of times you come out you leave those with a lot of key themes where you're like oh we need to continue doing this we should definitely stop doing this uh this isn't resonating but that was one thing that we put into practice that worked quite well yeah i can see that i think this is actually the second time i've had someone bring up retrospectives um and it's interesting to me because like i know retrospectives are like super popular for development um the development and then like sre and that kind of thing and then somehow in the marketing department i i seen i've seen a lot less of that emphasis um which is a bit of a shame because really like retrospectives just like as a whole is just a good way of improving processes yes really taking the time to intentionally ask yourself, like, is the process working? What's not, what is, how do we fix it? And just like making the team go through the exercise is like, it's just valuable for every team. And it sounds like you can kind of use it to coordinate marketing and sales together as well. Yeah. Yeah. And that's, you know, looping back to the cultural elements, right? Like. Is your team okay? And is it okay to fail on your team? Like, can we look at our work after it's been accomplished and say, this didn't really do it. And you actually don't get in trouble. Like you're actually praised because you critically look at your own work and say, I just think that kind of fell flat. Like I tried hard on that. It didn't really work. It didn't resonate. And there aren't like disciplinary actions that happen as a result of that. Like that's a hard culture to create, but it's super important. because if we can't look at our work and say like okay that that was good or that was not good um then what are we really doing here how are we going to get better at all and how we create better and new ideas if we can't reflect on what's been good and what's not been good without a fear of repercussion yeah and that's the tough part is like a lot of businesses there's i feel like kpis okay ours a lot of these things there's kind of this success fail mindset and it's like it's purely boolean like you succeeded or you failed. And so it is. And with that kind of black and white culture, there's no gray area of like, look, we're doing some things that are experiments and they could, you know, quote unquote fail, but it's not really failure. It's learning. You know what I mean? It's tough to, to like create that sort of culture. I don't know if you have any advice on like how any, any founders or CMOs or really anybody could sort of like create that culture or encourage it. Yeah. Well, um, So there's a more general perspective and then a very specific actionable piece that you can do. From a general perspective, I was the first one as CEO of the company to admit failure. I called myself out. Like that didn't work that well. This part was maybe okay, but this was not good enough. Like we need to change this. And maybe I was a little bit too hasty on getting this posted. Maybe I should have gotten some more feedback from the team. you know by self-admitting your own failures it opens up the door for others to do the same thing like this is okay and like it doesn't make me a bad person doesn't make me bad at my job like one piece does not mean you know it's not reflective of the holistic here and so what we were in a similar kind of retrospective kind of framework um this is another tech stars piece they call it the weekly 808 it was held at 808 pm uh every thursday um where it was, you reflected on like key learnings from the week, the win of the week, the failure in the ditch award. So if you really messed up, but this all had to be self-admitted. You can't, you're not really saying, oh, Jane really messed up on this thing. She's in the ditch this week. It's all self-admitted. So you have to say it yourself. And if you get the in the ditch award of the week, you win the like award of the week. And for them, it was a huge, it was a hubcap from a car. that was about you know yay big and they put it around a chain on your neck and that was your your win of the week or i guess in the ditch award uh they had one for a win of the week as well but it offered a sense of like humor to failure which i think is good has to be self-admitting you can give praise to others on when they did really good work but failures have to be self-admitted and that was a weekly cadence for us we did it at 3.03 pm obviously not based out of denver um but we kind of carried that forward and ran that for years. And I just gave it a space to give praise to people where they needed it and self admit failure when that happened. Yeah. There's a lot of good stuff in that just like psychologically. Cause I think part of it is like you say, the, the self admission part. is getting people it's not like a blame game you're not getting people to say someone else you know did something wrong and creating that kind of culture it's it's just you reflecting upon yourself and being able to admit that you do things wrong and that's you know the opportunity to learn really um and in in some ways it's very powerful psychologically especially to do it weekly because one of the things i've just seen uh and i am not thinking of anyone in particular or anything like this but i'll just say like sometimes i've seen companies where where like the number one thing i think that was blocking an executive was themselves you know or or a founder and it's like the thing that held them back was them it wasn't necessarily like there's always a reason you know it's always you know that sales isn't doing enough for marketing isn't doing enough the competition's too stiff the market's really hard vcs don't understand there's a million reasons out there but sometimes it just comes down to like we have some assumption in our own heads that just ain't so and as long as we operate on that assumption like we're gonna have issues and so i've seen like the number one problem an executive has is getting out of their own way sometimes. Um, and so having that like psychological routine, just every week of saying like, Hey, here's maybe, you know, where I messed up also opens up this culture of like, maybe I'm blocking myself again, you know, maybe, maybe I'm, I'm the problem here. Um, and so I think it's just good psychologically and it helps people sort of cultivate themselves. If that makes sense. Certainly when, you know, I had the perspective too, of. If something is wrong in the business, I want to know today versus tomorrow. And I prefer to know yesterday. I want to know immediately. And it's okay. It's fine. My specialty is I solve problems. I can solve a lot of different problems. I'm an ocean of ideas. And so if something didn't go well, I want to know about it quickly so we can course correct and I can help to train and make sure it doesn't happen again. but a lot of times there's a lot of fear associated with admitting those pieces like oh man especially if you really mess up it's like oh man that was really bad i'd rather just hopefully i can just kind of sweep it under the rug and nobody will notice it's just really not the the right way to go about building a culture or company and particularly when it comes to creating collaboration amongst teams where there can be a bit at odds sales and engineering can be similar like at times it's build better products sell better type of thing And that's just, you're at odds then. It doesn't open up for collaboration there. And so I think that's really important. Yeah. Yeah. It kind of reminds me a little bit of, I don't know if you've ever read Creativity Inc. by, I think it's Ed Catmull. No, I don't think so. That one is, so it's basically about sort of the life story, if you will, of Pixar. And there's like this one like really short period, really short blurb in there where I think Catmull is talking about how basically you get to a certain level of scale, like as a, as a founder where you just know that there's a problem brewing somewhere, like somewhere in the organization, there is a problem. It's not if, but the question is how fast can you find it? Like how fast can you detect it before it sets on fire and then tackle it really hard and then go find your next one. And that was like a really interesting, you know, like it, I knew that. like at an intuitive level but i had never thought of it at a conscious level but it's like so true when you're at that founding level you're like look it's a startup we have all kinds of problems we got more problems than we have man hours like that's that's just a god-given fact um but it's like which one is my next biggest problem i may not even know and like how can i get how do i find it fast enough that's really before it blows up on you because sometimes you know it has an expiration date if you will for sure And so that's kind of like when you come from that culture, it's easy to have a culture of thinking like, look, there are problems. There are things we need to improve on. And you can do the kind of like the 808 strategy or, you know, 303 or something like that. Whereas sometimes I look at the larger companies and, you know, like more established way past series, you know, D or something like that. And they start to have that culture where there's like layers of middle management and people don't want to like send problems up the chain. they kind of want to be like oh well that problem isn't too too big we already have solutions it's fine you know like you start to get that culture i'm curious if you have any advice on like as people scale how do they still maintain that culture of like look we have problems and let's tackle them quickly yeah for sure yeah i mean as you add these different like layers of kind of bureaucracy um I can't say that we ever got to the scale where that would be even close to a problem, but what I have heard other people do, I think it's called skip level interviews, where maybe a VP of sales would have a discussion with an account executive, not the director or manager. It's like, I want to go directly down two levels intentionally, not... to chastise or discipline anybody or like like usually when you have those conversations with the vp sales like oh this is not a good thing or you know what have you it's pretty binary it's either really good or really bad but if they make it a habit to have a discussion with people that are multiple layers below them um and i think it has to happen that direction right like for an account executive go up to a vp and say i want to deliver some really good feedback to you about where i'm seeing gat like that could be a little bit rough so it has to be invited by that senior leader but then you're not you're kind of going straight to uh the source of the information and it won't be diluted or distilled in any sort of way you get it right from them but again that's a tough thing to when you have those layers to create a culture where that's invited and welcomed as you have those discussions yeah and that one is always interesting to me just like as you introduce those layers you know like as you watch the startups turn into more like scale-ups and the culture kind of shifts um it's a very interesting time and to me i i totally forget what they call it like a reality distortion field or something like that around management and you know how it is like the higher up in management you go the more you get this like game of telephone coming up to you from the bottom and every time people are you know going to kind of under report the problem and sort of over report the solution every time it goes up the chain and by the time it gets to like you know ceo founder it's just kind of like you're sitting there thinking am i really getting the reality here like am i actually getting boots on the ground stuff and i i've heard some very different approaches to that you know one yeah one like what you're saying is sort of like skip level interviews if i understand that correctly where you you can kind of talk to a couple layers below you rather than just relying on the reports, you know, that you're getting from the person directly below you. Um, I I've known some people who said, and this is probably the politically incorrect term, but they said a good CEO has a spy network. Um, and it is like, they have a few key people in every department at the lowest levels that they know are just gonna like lay it out and they can go to lunch with this person. And just like, this is not someone who. wants to politic the ceo or anything like that there's no it's just purely they're just gonna talk like here's what's going on good bad everything ugly um and they can kind of like give visibility that that's one i've i've heard as well um and then i i always remember i'm going off on a tangent with this one but i i always remember um i think it's kfc actually the colonel had this whole thing about making sure that every location got the kentucky fried chicken like correct because i mean it's literally called kentucky fried chicken um but some locations would get a little lazy in the way that they did the kentucky fried chicken and it was just kind of chicken right it was yeah it wasn't special and yeah the colonel was not happy with that and so he made this like this culture where he could um if i remember correctly he could show up pretty much anywhere in the country at any kfc location completely unannounced no preparation whatsoever he would just drive in and he'd walk up and he'd order the chicken and he would eat it like a normal customer and he if he was happy with it great but if he wasn't happy with it he would like go back into the kitchen and he'd say all right throw everything out i don't even care if it's like the lunch rush throw everything out he'd pull out his own apron and he would show everyone how to make kfc correctly all right there on on the spot and that i love it yeah and so it's like he always you know had that ground level connection he wasn't just going to rely on a bunch of reports he was like he went and he ordered the chicken and he knew if it was truly kentucky fried chicken which i mean if it's if kfc isn't serving good kfc then like what's the whole point exactly and so like he would go in and you tell people like here's how you do the chicken kind of seems like That would also instill a little bit of a culture of fear and paranoia, but maybe the right sense of urgency. For sure. And he knew what was going on at the lowest level. I think one thing that's interesting or important to highlight about that story is managers that will actually show you the way versus tell you how to do it. It's one thing if you do something wrong and everyone's just saying, do it better. But you're like, well, I did it as best as I can. How? But he showed them the how. He got his hands dirty. He was like, you know what? This is a problem, but I'm going to help you fix it. And so what I would hope or expect is that, you know, yeah, there's a bit of paranoia or fear there, but that if you're caught, we can help to solve the solution and he's not afraid to get his hands dirty. Like, I like that a lot. And I think that's really deeply missed amongst many leaders today, especially when you get into big organizations where. a little bit too hesitant or fearful to do the work and show them the path on how to make it better. Yeah. Yeah. It's easy to fall into the routine of saying like, well, that result is bad, but then not be able to actually help that person improve the process so it doesn't happen again or, you know, like work it, you know? Precisely. Yeah. I mean, that makes a lot of sense, but I was going off on a bit of a tangent with that one. Yeah, that was great. But it sounds like, you know, kind of coming back to where you were, you were sort of thinking about like, how can you expand this messaging to AEs? And you were, you know, kind of going through, I think this sort of like retrospective and sort of seeing like, okay, what content resonated last, you know, last quarter? What content do we want to try and say repurpose or try something new with the next quarter? I'm curious, like when you're looking at the content that resonated or didn't, What are like the specific metrics or things that really tell you like, hey, this resonated versus like what didn't? How do you know when something died on the vine? Yeah, for sure. Well, I think there's a lot of things you can look at and you don't want to put too much weight on any which one of these. Like, you know, for any social media posts, it's like likes, comments, shares, impressions. Those are obviously indicators on the video standpoint, like how many views are you getting? But then how far are they actually? watching that video, if they're watching it for a few seconds and then dropping, well, okay, maybe we need to get better at our hooks in the beginning. Or if people aren't even clicking on stuff, maybe the images aren't quite there. And so you almost kind of like correlate different metrics to different parts of content. A really key part of this is making sure you have good UTM tracking on blog posts that are coming out there. I mean, the ultimate measure is paying customers, of course. And so I kind of split these out into your leading metrics and your lagging metrics. Like lagging metrics are typically revenue, qualified leads, customers, revenues, on and so forth. Fairly easy things to point out. But then there are the leading pieces, which are breadcrumbs that could give you indications on, okay, we didn't get a customer out of this one, but man, did this really get a lot of impressions here? Let's analyze about maybe what we did well, what we did not do well here. you know people are watching it for much longer than they have in the past so let's try to take key learnings from the static images we're putting out there the hook in the beginning half um so on and so forth so we were kind of looking at all of that and we we really i'll say when we started we were not great at this we're not great at this and it kind of felt like we were just spinning our wheels and you know doing putting out stuff there just to do it not that it wasn't really it wasn't really translating too much And then we kind of refine that with time and be like, okay, is this actually doing anything? And how do we know? So we did it the wrong way to get started and we gradually got better at it with time. Yeah, I would say like, so, you know, I come from an SEO agency and we specifically focus on SEO content specifically just to like rank. And so we're working with the content team very, very closely. I'd say that that's most startups though is like, First, it's like, hey, let's just do content so that we have content at all. Let's get into the habit of doing it. And then at some point, someone says, oh man, we've been working really hard on this. Has it been working? And then they worry about like, oh, we should probably put like UTM tags on stuff and track it and look at our metrics and that kind of thing. But it always happens to stage two. Like first, they got to get into the habit. Then they get into measuring. I guess any advice on... either A, just getting the team into the habit or B, like how to get that measurement upfront and early in the process. Yeah, well, I would urge people to follow more or less the same path I did. Like, and this may be counter to what people think is like, well, you should have all your tracking in place before you get going. And that probably is best practice. But for the early stage founders who don't have as many resources and have to really pick what they're focused on, I'm like, You just got to start. You got to begin. And so what I did is when I started to create content, I'm like, we should start to put an emphasis behind this outbound, maybe getting a bit stale. How can we try to revamp that and pair that with a nice content strategy? Like generate a list of 100 different content ideas, start there, break it down into categories of content or topics or themes. And then that helps with a lot of the friction of creating content is like, what am I going to talk about? What are the topics here? Well, now if you have a menu to choose from, now you can really build those habits much more easily. And so I thought about like, where's the biggest friction points or the things that take me the most time to get this done? And how do I make that easier for myself? And so I do think that people should try not to overanalyze things in the beginning half, try to build the habits first and then like, okay, let's refine with time. Like you're not going for perfect right out the gates. Because if you aim for a perfect podcast, I'll do 10 in the same timeline it took you to get two done or one done. And I'll have refined it and got it better in that same amount of time. And the learnings I'll have taken from that is my 10th video podcast will be five times better than your first one because of just the lessons I've learned along the way. Yeah, it's very much a case of like, don't let perfection be the enemy of progress. Because I think that's really the thing is sometimes we look at the best practices and say like, here's how the big companies are like doing the content they've got all the tracking and they've got their six cents set up and all that kind of stuff and it's great but what you don't see is like they they built that over the course of like five to ten years to get up to that point it happens step by step but people are told like hey you need to jump to that that stage like today and it's like no it's not gonna happen yeah yeah no it's nor should it i mean it's like unless you have you know you just raised a 10 million dollar a round or whatever and you already have marketing teams like if you're in a position where you have the resources to help yourself get to that spot great but a lot of times at least with the founders i'm working with and the company i was running we did not have that like we we didn't have those resources nor do we want to allocate capital at that specific stage and so we're really like the testing phase to try to get as much learnings as we can so when we do have the capital to spend that there we have more direction on what might work and what might not work. Yeah, that makes a lot of sense. I guess for the people who, it sounds like you start off with like, let's just get into a process. Let's reduce the friction as much as possible and just build a good habit of creating content. And some of that is like, if you have a good list of like a hundred ideas, maybe break it down. I've seen one where like people break it down by themes on one axis and then like. content format so like a storytelling format or a video format and they create like a content roadmap um you know that sort of thing and just using that to really build the process first um and then once they're there like how do they start getting into like measuring it and knowing that it's working or it's not working like if someone is just embarking on that part of the journey absolutely absolutely yeah and another principle i tried to follow and this is not my idea this is gary vandercheck i think he did uh that jab jab right hook he did crush it he just did another one called uh day trading attention in terms of books that he's launched out there but what he kind of said is okay if you do a webinar like this one right now that we're on um okay after this is done we're gonna have long form content how can we split up into short form content which you're obviously doing uh how can we take the transcript and create a blog post how can we take clips from this and create static images where you take one piece of content you make 10 different things out of it which kind of all directs back at the same place. Again, that's another kind of micro experiment on, you know, getting pieces out there that kind of, it's amplifying effort that you've already done and creating many different pieces across many different social platforms just to see what resonates within one piece of content. Yeah, yeah, that kind of, that makes sense. So it's like, you can use the content that you have, repurpose it 10 different ways and in and of that, like you see which parts get more traction than others and that kind of gives you even more of a sort of almost an a b test in a way on like which parts are getting more traction i never thought about that aspect of it but i know right now like ross simmons is also on that that uh whole train of like redistribute for life yeah yeah for sure yeah i mean that that's a good one i guess overall i mean it kind of sounds like A lot of it is, hey, just send content out there first, like get into the process of doing it, get into the process of measuring it, get into the process of repurposing it and remeasuring those aspects of it. And then once you're there, you kind of get into a good loop of, you know, like knowing what works and what doesn't. I guess I'm curious if you just have any like good stories or examples where you kind of like went through that process and you finally got to something that like was really resonating, really working and you thought like. Yeah, we're nailing it here, you know? Yeah. Let me think on that. You know, we did a we did a partnership with a group called the Pre-Sales Collective. They're a group of sales engineers, solution consultants, and we tried a lot of different stuff with that organization. So I did I did in person sponsored events. I did written blog posts for them and. what we kind of learned maybe through the blog post is that didn't really quite resonate as much but we took that blog post and we chopped it up and created a six-part video series which more or less explained the same principles that were within there but they were short form content so it wasn't super long as maybe five six minutes a piece but five or six videos and that got way more traction than like a blog post would because it was a series that people follow in sequence and so if you one thing catches your eye we can easily move you on to the next piece there all of it was more or less the similar type of messaging that was in a blog post this could be an seo problem that we had potentially uh because nobody found the blog post but um i think that was one way we learned and we're like well this is good stuff here we like what we wrote um you know and here's another example for you too as well I found that interview style blog or video posts were better and performed better than just me as a single person, which kind of makes sense. It's like I post something out there. You, Lee, is whoever I'm interviewing. You're going to repost that. And so that was an indicator for us. And so another strategy we tried was the top sales tech, six best sales technologies that we see out in the marketplace, where we look at six different solutions out there, promote the ones we thought were the best. but then all of those companies would repost comment share employees there so the reach was a bit broader um so we kind of took these key learnings here both from the pre-sales collective on kind of format of content but then also a totally different kind of use case was oh wow when you add other people into this and other companies that tends to have a little bit bigger reach and more engagement on those posts so we should try to keep doing this like this is a good thing here um and gave us indications on you know consistency we should be trying uh in the formatting yeah that makes a lot of sense in more than a few ways firstly that the long it sounds like the short form video content aspect and then also the the collaborative content um i guess if someone is out there they're listening to this and they're kind of thinking along the same lines where they're like i'd really love to do something like that and start like iterating and kind of going through this process What would you tell them in terms of like how to go through this process and start doing it for them? Yeah. Well, one thing I've been doing recently, you know, I think, you know, AI and ChatGPT is changing kind of the game for a lot of people and there's more content out there than ever. I do think it's important. Like, I think people can kind of sniff out if it was totally written by ChatGPT. I think you can kind of see that from a distance. But I like to do it for idea generation. So when I record a piece of content like this, I'll take the entire transcript and say, generate ideas for me based upon what we discussed here. So that's one way to kind of repurpose that, but it's using my language, not the ChatGPT's language. I'm like, in my voice, write this out. I'll get ideas there. And then I take the highlights and I rewrite it based upon more specifically what I would be doing. And so I do that for video ideas I take I want to create a blog post from this video I just did and that is kind of an amplifier there but I do think the like going back and going back over it again with your own voice is important because I think people again I think people can kind of sniff out the chat GPT written pieces but I do really like it for idea generation I like it for taking stuff I've already said and creating ideas from that I like that quite a bit Yeah. You know, it's always interesting to me because everyone's kind of exploring right now where AI helps and where it doesn't sort of seeing with the beginning and the end of that. And I feel like early on there was this hype of like, oh man, we're only five years out from AI super intelligence and we're going to get to singularity and it's going to take everyone's jobs. And now I think we've been a couple of years out from the beginning of that hype cycle. And the expectations have become more realistic. And it's interesting just how many people are like, yeah, AI, it assists, but it really doesn't replace a lot of, a lot of this content. And I do believe like it, it helps take aggregates of things. If you know what I mean? Like say like a whole podcast, you know, transcript for example, and then really. boil that down into a few things that are like very scannable or a good idea generation and it assists it accelerates the process but people are still looking for that human voice in the content they're still looking for you know personality and tone and that kind of thing and so like i i might even go so far as using ai for like a first draft on something but then it needs to be like a human human needs to do it you know it's a human talking to humans yes And so that helps a bunch. But it sounds like overall, if someone's really starting out on this, just kind of piecing together some of the things you've said, they should really start with just creating a process for creating content. Just do it, basically. Reduce the friction points, maybe have a list of good ideas, and just get into the habit of doing content on a regular basis. And then from there, Create a regular routine of measuring it. So like if they're looking on LinkedIn, what are the impressions? What are you know, like what's the engagements? What's the comments? These sorts of things. Same thing if they're doing YouTube or something else like that. If they're on SEO, I can always say like, are you ranking? Are you driving traffic? Does it do anything that looks like it's converting down funnel? Those those three are usually your golden metrics there. But just like start getting into the habit of tracking the content. and looking back on it and then from there you'll see what works what doesn't and that gives you ideas going into the next quarter what ideas to try and what not to try and that kind of thing and then once people are getting through through that loop then also thinking about like how can we use maybe a little bit of ai or like content repurposing and then breathing some new life into this content, seeing how these variants do well and those variants don't. What does that mean? Then once you're in the loop, that'll tell you a lot of the messaging you need and then that might inform at some times what sales might be more interested in or maybe what marketing should be covering more of and trying to cross-collaborate between those two departments. Does that sum everything up there? Absolutely. One of the things I wanted to mention that I haven't quite yet is probably the i think the number one rule of content that is the most important piece and it's an 80 20 split you need to be talking about the problems in the industry 80 of the time your audience what are they struggling with and you can only do self-promoting talking about your product service what you're offering 20 of the time one day a week so if you're doing five posts a day or five posts a week like you get one that is more self-promoting Because if you do too much self-promotion, check out this demo, look at this feature. We just launched with X, Y, and Z customer. Check out our website, blah, blah, blah. It gets really stale really quickly. And it's just too much. It's content for you and your company. It's not content for your audience. And so you have to keep a really careful eye on who is this built for? And am I really trying to help my audience figure out problems or solutions and talk to that? Or am I... just trying to get them to buy my stuff like so that's a really delicate balance there and too many people really sway towards self-promoting when they really should be focused more on you know i even into this point it's like with my demo product right so i had a demo product out there i thought okay if i if demo flow didn't exist what type of content would i put out there how would i help people solve these problems without my solution And that's what I talk to is that the problems and potential solutions out there had nothing to do with my direct problem or my direct solution that I provided. So I think that kind of helped as a lens to look at the content strategy through and ways to ideate on ideas that you can be putting out there as a result. Yeah, I'm in a very similar camp because I feel like, especially on LinkedIn. I feel like LinkedIn has more of that kind of standard post where people are like, Hey, we just launched a thing. Look at our thing, you know, and it gets very self-promotional or it's like, Hey, we're going to go do an event. Isn't that great? You know what I mean? Um, and it's easy, I think for the content team to get stuck inside its own, you know, its own white boarding session, if you will, and focus on what they want to write. and that to me is like the number one problem in content is we're all spending a lot of time way more time than we should writing what we want to write but not necessarily writing what other people want to read and knowing like what's resonating it's like half my job as an seo is just to help people understand what it is that people are searching for And what questions are those searchers asking, basically? That's the way I always put it. Searchers are asking Google a question. You just need to give them the answer. But you have to start with, what is it that this person's going through? And as an SEO, I can kind of help analyze that and give the perspective of, here's what the searcher's asking you for. OK, now, how do you help with that? Firstly, by just giving them the answer to their question or the solution to their problem. And then if you can weave in some of your messaging into that, that's great. But it's got to be part of the solution for this person. You know, it's tough because, again, it's like one of these things that we kind of know subconsciously and we all talk about it, but it's very difficult to create a culture of really thinking reader first and then our messaging second. And it's just I don't know. I've never found a good magical way of just getting people to like always think that way. It's easy to fall out of. For sure. For sure. It really is. And it's always a. That type of content is the easy way to go about doing it. Self-promoting yourself. And we got this event coming up. That's easy stuff. That's not hard. You didn't really stretch to think super deeply about that. So it is the easier way to go, but it's less effective without question. Yeah. I think you've kind of given a lot of really good thinking for a lot of people out there. I'll probably have to meditate on a few of these things as well. But I'm curious, like if people are interested in finding you or StairStep Strategies, where can they go to find you? Yeah, so LinkedIn is going to be a great spot. Super active on LinkedIn, as we were talking about. Lots of content we're putting out there, but name is Larson Stair. Just search me and you can find me there. Also, my email is Larson at StairStepStrategies.com. Website is StairStepStrategies.com. Well, I could have guessed that one, but yeah, reach out to me on there. Happy to have a deeper discussion with anyone who might be interested, but yeah, feel free to get in touch with me. Yeah, sounds good. Well, thanks again for coming on the podcast. Yeah, I really appreciate it, Lee. Thanks for having me here today. That was Larson Stare, founder and CEO of Stare Step Strategies. You can find him on LinkedIn and you can find his company at stairstepstrategies.com. I'm your host, Lee Cooper, and it takes me a long time to put together these podcasts, so I'd love it if you take... only a second to rate and review this episode in your podcast player of choice or if you're on youtube just take a second to hit the like button and subscribe to make sure you get the upcoming episodes i'll see you next time

Welcome to the Tech Marketing Masters Podcast, where we interview CMOs and VPs of Marketing in tech to give you an inside look at
* What other tech marketing execs are up to
* What’s working in marketing these days
* What you can try with your team
* And how to level up your marketing game

I’m your host, Lee Cooper, Co-Founder & CEO of Cooper, the SEO marketing agency that helps tech companies grow their organic search traffic.

I’m joined by Larson Stair, Founder & CEO of StairStep Strategies, which helps Seed-stage start-ups build a revenue engine that unlocks a new phase of growth.

Today we explore a lot of great insights like
* How to quickly test new messaging with content marketing (and how to create a process of rapid experimentation)
* How early-stage startups should zero in on their first ICP (and the importance of crafting messaging unique to each additional persona)
* How marketing and sales can share insights into which messaging is resonating (while maintaining at least some brand consistency across departments)
* How TechStars’ Weekly 8:08 retrospectives can help your team create a culture of honest self-accountability and experimentation (and their In the Ditch Award can immunize your people from a paralyzing fear of failure)
* How to use skip-level interviews to maintain visibility even in larger, scaling organizations (and the importance giving feedback that also shows people a way forward)
* How your team can build a strong habit of creating content early on (and then get into the habit of measuring the effectiveness of their messaging)
* Ways to repurpose content for even faster iteration and experimentation (including some reasonable tricks to using AI without losing your human voice)
* And the 80/20 rule to use when writing your content that makes sure content resonates with your audience (more than it promotes yourself)

If you’re interested in any of these things, then you won’t want to miss this episode.