How to Be a Standout Startup

 

Drew: Hello, Renegade Marketers! If this is your first time listening, welcome, and if you’re a regular listener, welcome back. Before I present this episode, I’m thrilled to announce the first-ever in-person CMO Super Huddle that we’re hosting in Palo Alto on November 8, 2024. The theme is “Daring Greatness in 2025” and we’re rocking a full slate of inspiring speakers with ample time for networking. Early Bird tickets are on sale now, so grab yours at cmohuddles.com. It’s gonna be flocking amazing!

You’re about to listen to a Career Huddle where our B2B CMO community, CMO Huddles, gets exclusive access to the authors of some of the world’s best-selling and important business books. The author of this particular Huddle was Allyson Letteri, who will be at our Super Huddle, by the way, consider this your sneak peek into her insights. In the show today we dive into her book, one I couldn’t recommend enough. It’s called “Standout Startup.” We talk about common positioning mistakes B2B marketers are making right now, how to define marketing to the C-suite, and what to do if you have too many personas. Allyson also shares case studies involving QuickBooks and Handshake and gives a fantastic view into what makes irresistible marketing. If you like what you hear, please subscribe to the podcast and leave a review. You’ll be supporting our quest to be the number one B2B marketing podcast. Alright, let’s dive in.

Narrator: Welcome to Renegade Marketers Unite, possibly the best weekly podcast for CMOs and everyone else looking for innovative ways to transform their brand, drive demand, and just plain cut through. Proving that B2B does not mean boring to business. Here’s your host and Chief Marketing Renegade, Drew Neisser.

Drew: Hello, Huddlers! I’m excited to introduce you to Allyson Letteri, author of “Standout Startup.” That’s this book right here. Standout Startup. Allyson is an accomplished marketer. She led QuickBooks customer marketing globally and grew several startups into standouts, including Handshake and Thumbtack, both of which achieved unicorn status before she left, and they were in their startup form when she got there. While her book focuses on helping founders find their marketing mojo, her strategic approach is refreshingly simple and worthy of a closer look by just about any marketer. So with that, welcome Allyson, how are you and where are you this wonderful day?

Allyson: Hi Drew. Thank you so much. I am in sunny San Francisco right now. It’s beautiful.

Drew: Well, there you go. You know, no fog, nothing, huh?

Allyson: No, we got a clear one.

Drew: Well, there you go. One of the things I’m trying to do is get right to it. So just in case the audience has to leave early, or we need to persuade them to stick around. Could you provide three most common mistakes you see brands making right now?

Allyson: Absolutely. The first I’ll call out is messaging, which is a perennial problem no matter how big the company is, but making sure the company stays agile and is adjusting their messaging to keep up with the product, changes in customer needs, changes in competitors. I’m hearing a lot, you know, with AI, differentiators that they used to emphasize don’t work anymore. So how do you stay on top of messaging so it reflects your best value? The second one, I’d say, is just content fragmentation. I’m always amazed at how much effort companies are putting into content creation and not getting the full value of distribution. So they’re creating so much, but too few eyeballs are seeing it, too few people in the right audience. So streamlining content creation and distribution. And the third, I’d say, and this might apply more to earlier stage companies that I work with, but this desire to create a category, and this can be such a distraction and so time-consuming. So I’ll leave it with those three challenges, and happy to talk through any of them.

Drew: Yeah, and let’s go through them one by one because they are so interesting. So let’s do some definitions here. When you say messaging, what do you mean? And you know, there are certain things like positioning, I feel like should have some endurance, but messaging may be something that you sort of have to pivot on with some kind of frequency. So can you help clarify what you mean by messaging and what we’re talking about here?

Allyson: Sure. So I think of messaging on two main levels. The first is company level messaging. So your vision, you know, what’s the reason your company exists, what’s the big change you’re trying to create in the world? And then your mission, which is, how is your company specifically helping customers achieve a benefit to advance towards achieving that big vision? And then this also includes your company values, potentially your founding story, your brand story, so that company level messaging. What I focus most of my time on is actually product messaging, and this is explaining to your ideal customers why your product is highly valuable to them and also better than any of the alternatives that could also be valuable to them, so valuable and differentiated. And many times, it’s that product messaging that needs to be updated more frequently, and it is an output of understanding who your ideal customer is, what makes you different and better, and also your personality. How do you want to show up as a brand? So with those ingredients, you can come up with really effective messaging.

Drew: Really helpful. So as we dive into product messaging, and I know that the hardest job to fill for CMOs in our community is the product marketer, and in theory, that’s where product marketing and the messaging should gel, right? Because they understand the product in theory, they understand the customer, so that they can create this value proposition that is, in fact, differentiated and clear, as opposed to what I often hear is a feature set.

Allyson: Yes, exactly. I think the fastest path to being able to solve the product messaging problem is hire a really talented product marketer that has that connective tissue between the product team, understanding not just the feature list that’s about to be shipped, but why those features matter, and how they ladder up to the benefits you’re already talking about. Are they delivering more value within a certain benefit that you’re already emphasizing, or is it generating a totally new type of value? So you really need to update your messaging, but then also playing the connective tissue with the sales team, because the sales team is on the front lines, obviously talking to prospects and customers daily, and their messaging can lag, or they might be out ahead of marketing and product. If product and marketing aren’t working together to define the value of those features, you know, they’ve got to figure out a more compelling way to describe what you’re doing and why it’s the best fit for a customer. So product marketing can really be the glue that ties all three of those groups together.

Drew: Interesting, and it’s funny, because we haven’t had many conversations about product marketing and sales, and so I’d love to hear from them, from the audience who’s listening now, are your product marketer persons meeting regularly? Do they have a cadence with their sales partner? Because we just haven’t, believe it or not, talked much about that in Huddles, and that feels like either something I’ve just neglected or it’s just happening no matter what, and all is good in that relationship land.

Drew: Okay, so from a product messaging standpoint, we’ve got that. And there’s a question already from the audience, which is, how do we align that across the company and marketing faces and teams, if you’re iterating often, right? So you’ve got this message and then you’re changing it or so forth. So this alignment thing is a big deal because again, we get back to fragmentation and peanut butter effect and all of that, right?

Allyson: Right. I think that’s why messaging is such a pinch point because it does get outdated quickly in many cases, especially if you’re a fast-moving tech company. So the first thing is a mindset issue. You need to expect that you will have to iterate so making sure your website is modular and easy to update. It’s so painful when you have to rely on an agency or an external engineer anytime you need to tweak anything, thinking about, frankly, simplifying some of the key pieces of content you have because, you know, they’ll need to be refreshed often, and so proliferation of content creates an even bigger beast to manage. I like to think of the happy path for your prospect and your customer? What are the most essential pieces of content that help them move toward deciding to buy your product and then onboard effectively and use the key features to get the results you promise and know what those essential pieces of content are so that you can update the messaging easily. And then I think quarterly cycles are really helpful so product, knowing that marketing is on a quarterly basis, or at least twice a year, going to reevaluate messaging, give significant updates to the sales team, tweak pages in the sales deck, update one pagers, so that there’s this expectation that you’ll always be making changes, but what the new messages should be is rooted in a process that I think we’ll talk more about today. And if you can’t hire a product marketer, or, frankly, if you just want to invest in learning the process, I’m hoping that you’ll have a better sense of the steps to go through to get to great messaging after we go through this conversation.

Drew: Awesome. And what, as it occurs to me that I don’t know, and I feel like sometimes there’s this disconnect where product marketing sort of hands—here’s the messaging sales. Off you go. And should there be a feedback loop here so that someone from sales is actually part of getting that messaging shape, so that they don’t say, “Wow, that would never work.”

Allyson: Definitely. Well, it starts with the original messaging creation, or wherever you are in your messaging journey, bring in sales from the very beginning to align on this definition of target customer, your ideal customer, which in B2B companies, of course, starts with alignment around your ICP. What are the types of companies that will get the best results and that are the best fit? And then who is the buying committee that will weigh in on your solution versus other solutions in which to buy, and then choosing that primary buyer, and that’s very likely the first persona that you want to create messaging for, because that’s the person whose attention you’re trying to catch through all of your acquisition efforts. And then once you’re on their radar, that’s the person that you need to nurture and convince and also equip with the right information to go back into their company in order to talk about why your solution is the best fit. So sales needs to feel very aligned with marketing on who you’re talking to, and also what’s the information that would be most useful in moving someone toward being a qualified lead or moving the sales conversation forward at each point in that journey. And sales has a lot of insight around that. So it’s a real disconnect if marketing is trying to figure that out in a vacuum, and ultimately in B2B, sales is closing the sale. And so while the website and other marketing touchpoints do need to work hard, sales is on the hook for closing that. So we need to make sure that marketing is playing a really strong enabling role once the conversation gets into the hands of sales.

Drew: And it occurs to me at this point, it’s like one thing—this alignment of marketing and sales is so critical in this. Do you encourage folks that are in marketing to get on the front line and spend some time with sales actually going through sales calls?

Allyson: Absolutely. Yeah, that’s great. You will learn so much and beyond that, also sit with the customer support team, listen to what customers are saying about what’s working with the product and what’s not. Certainly, if they’re churning, what are some of the churn reasons? Where are they going? So when we’re thinking about customer discovery and laying this groundwork before you create messaging, taking advantage of all of these teams who are talking directly to customers is, I think, just as important, or maybe more important, than spinning up a new customer research project when you’re trying to, you know, book 20 interviews and go through. So yes, spend time with sales. And for early stage companies, founders are often doing a lot of founder-led sales. So they are the head of sales, and they might be one of just a couple of salespeople in the organization. So many times they already have these insights. They just don’t necessarily think of themselves as marketers yet. And so we need to kind of harness that and turn it into the marketing elements that lead to messaging, to get that out of their head.

Drew: It’s funny, you say that, because I think a lot of the CMOs—let’s say the founder is still in charge, and there’s 500 people in the company. They still think that they’re the Head of Sales, and they may not know marketing, but we’ll get there in a second. You mentioned early on content fragmentation as a problem. We always looked at it as, is there one big content program as a pillar and then all sorts of slicing and dicing of it so that there’s sort of one big message in the market at a time, at least for a specific group of people, but I see fragmentation everywhere. But then you also mentioned this happy path, which I love that notion. And so it feels like if we can stop fragmentation and we focus on the happy path, then in effect, we may solve the fragmentation problem.

Allyson: Right. So I often see companies having, really like, three content programs running in parallel. The first I do think of as this happy path, more evergreen content, that once you catch someone’s attention, you’ve attracted them. That’s kind of the first phase of the customer journey. Then you move into the nurture phase. So what is the content that proves your product is differentiated and is better than the alternatives, and that shows your product is delivering results, and so that often means a lot of customer case studies, comparisons with other products, they’re showing why your way is better and will get a customer a better outcome. And then there’s more conversion-specific content that really gets into the nitty-gritty of the product and pricing and any of the details that someone needs to feel very clear and confident about before they make that final purchase decision. And then there’s onboarding content. How can you guide someone to take the right steps, to accelerate their time to value as a new user and in B2B, and Account management team is often involved in that too. And then finally, how are you engaging someone long-term? So that’s lifecycle marketing, more evergreen. The second program that’s ongoing tends to be acquisition campaigns and Drew, you know, when you’re referencing one big message in the market, I think having a quarterly cadence is often a good place to start for a smaller company, and it can get more sophisticated over time. But what’s the big new idea you’re going to put in market to get on the radar of people who’ve never heard about your product before, or who are passively looking maybe have heard about you, but you want to make sure to catch their attention. And then I’d say the third content program that’s often ongoing is more of a thought leadership brand-building awareness, a type of content that isn’t necessarily directly tied to measurable pipeline creation, but is definitely increasing your awareness in the market. It’s shifting perceptions or shaping perceptions around why your product is better than others. And so it sounds like this has to be fragmented, but what I encourage companies to do is plan on a quarterly cycle and think about the core pieces of content that enable at least a couple of those threads and that are tied to a seasonal theme, or a theme that’s very timely and relevant to your customers and your company. At that point, maybe it’s peak season for your customers. They’re going into a very busy season. So you know, they’re thinking about certain aspects of your product and what they need to do, the workflows they need to do to perform very well. And so choose that core content, focus on those intentional pieces, and then think about how you can slice and dice and distribute across a range of channels. For instance, how can one report become your social posts, become your pitch to podcasts or to the press, be sliced up to have some SEO juice and drive organic search results? So thinking really intentionally and thinking ahead to do more with fewer pieces of content is very helpful.

Drew: Yeah, I mean, that’s a lot. I mean, you mentioned five in the first group and the acquisition, obviously, most people are doing AB testing of a lot of different things, and then in the thought leadership thing, which feels squishy and is also trickier to budget for unless you’ve got a CEO who loves to get on as a thought leader. So both the second and the third, the acquisition and thought leadership, get back to this desire of folks to say we’re in a category by ourselves. And you mentioned in the beginning that that was problematic, and maybe even a graveyard for a lot of brands. Why are you anti or overemphasis on category creation?

Allyson: Right. So many of the startups I work with truly are doing something very innovative. They’re bringing a technology to market that is solving a problem in a way that that has not existed before. So in that way, they are truly unique. But the reality is, as soon as they begin sales conversations, they will be compared to some other solution that could be do nothing or something that the company has built in-house. It could be the company piecing together multiple solutions today to get to the same outcome that this one product would be able to do. But I really encourage companies to not waste the time trying to explain why you’re something they’ve never seen before, and explain the problem they’re solving, and rather get straight into these are the challenges you’re facing. This is the outcome you want. Our product does that better than anyone else, and let me tell you why we’re better than the other solutions you may be considering. It gets to a more pointed conversation, and the reality is, you will be compared to some other products. So I’d rather companies nail why they’re better first, and then hunt the category creation conversation. And even more specifically, it’s often define what category you’re in, and then choose a really unique modifier to show you are in that category, but you’re bringing something truly novel and different that’s really compelling.

Drew: Yeah, on that last point, one of my favorite examples, it’s in my book, is Wasabi that define themselves as hot cloud storage. And so hot cloud storage became their sort of, well, what’s hot cloud storage? Well, you know, it’s cloud storage, but it’s, it’s hot, I mean, but in the brand name is Wasabi. But it turned out they were 80% less than Amazon, and six times faster. So they did have a very strong and clear and simple value proposition there. But I wanted to go back to this other part of category creation. And the irony is, you know, you’ve created a category when: You have competition. Two, the analysts say that it’s a category, and three, that you have a community of users who are defining themselves with a job role like, you know, there wasn’t the category of—Tableau created the category of data visualization, but then suddenly there were people whose job it was to be data visualizers, and similarly so, anyway, that’s my thoughts on category creation. It’s lovely when it happens, but it’s a byproduct of really good differentiation and building community, as opposed to we’re going to create a category. So let’s step back for a second, because I think is really important in the scheme of things. How do you define marketing, and then how do you explain its value to the founders, CEOs that you deal with?

Allyson: A very practical definition of marketing that I work with every day is: marketing is the right mix of content and channels to acquire and retain customers, driving revenue growth. So it’s about content and channels, and it’s a mix of those acquisition and retention activities. When I’m talking with founders, two things I often say: one, if they’re not using marketing to help them generate leads or onboard and retain customers, they’re leaving a lot of growth levers on the table. There are a lot of channels that marketers have access to that reach your ideal audience and motivate them to take action that sales and product don’t have time to manage, and oftentimes don’t have expertise to manage. So why slow your growth? Why leave that on the table? 

The other thing that many founders, and I would say even maybe CEOs of later-stage companies, don’t fully understand is that marketing touches the full funnel, the full buyer journey, and the full customer journey. Many times, founders think of marketing purely as acquisition. Need more leads for sales? Need more qualified leads? How do I get that? That’s marketing’s job. But marketing can be just as powerful at making sure that those new users that you spend all the time and effort to acquire actually get value and stick with the product and retain past 90 days. Also, over time, as you’re releasing new features or building new capabilities or things are shifting, your customers are along for the ride, and they’re continuing to use the most important features of the product and adapting to changes to the product and pricing and other things over time.

Helping founders understand that, I think of five phases of the buyer journey: first attracting new leads, then nurturing them to believe you could be the right fit for them, then actually converting them into customers, then onboarding, and finally engagement. So over time, retention activities, and that tends to be a wow, like, “Oh yeah, there’s a lot we could do here,” and they’re excited to talk more about what that could be.

Drew: You know, you’re preaching to the choir here. What I did love about the definition is there was no doubt that at the end of this rainbow was driving revenue growth. So you didn’t get very far before you got to that. But the fact that they’re missing a lever. But, you know, there are still a lot of founders, CEOs, who, you know, maybe built a $100 million company on the strength of a great product that seemed to be able to get out there, you know, on a product-led growth strategy. And they still believe the market will find them if you just build this great product, even though we just showed them the five ways that marketing can impact them all the way through. How do you get those folks to become believers?

Allyson: Well, I like to say product innovation alone does not drive revenue, and so the CEOs that you’re talking about potentially got exceptionally lucky that their product made it so obvious how they overcome a certain challenge for a customer and get them to this highly desirable outcome. And there maybe aren’t a lot of competitors that do that in a compelling way. So much of marketing is really that transformation story. How do I take you out of pain and into gain? And how is our product the best bridge to get you there? 

But many times, when I’m working with a founder, they know something is off, so they’re feeling like their marketing touchpoints are chaotic. You know, I’ve talked to multiple founders that are like, “I know how to close a sale. If I get to talk to one of our prospects, I know they will buy, but I listen in to my sales team calls and they are not saying the same thing I am, and I don’t know where they got that messaging.” Or “I look at our website and it reflects two versions ago of our product. It is just weighing us down.” Or “I’m embarrassed to send our one-pagers. They don’t say the right thing.” So there’s this sense that the messaging is off, and potentially even the positioning, like, how do we explain why we are the best fit? And so there’s this foundational issue that they sense.

And then the other thing that tends to drive founders to say, “Okay, we got to figure this marketing thing out,” is just not enough leads. And so many times early-stage founders will start with this founder-led growth outbound focus purely on their network and the leads that their investors can give them, these warm introductions, and that dries up relatively quickly. And then just sticking with outbound marketing can be very inefficient and time-consuming. And so I’ve worked with a number of founders to really try to switch into, ideally, more of an inbound motion, but at a minimum, having some halo of brand and authority-building content so that if they do get someone to pick up the call or respond to the cold email, they can search online. And there’s a story, a compelling story about the product, but also create some of this happy path content we’ve talked about so that they’re not purely relying on the sales conversation to close. There’s other content that helps tell the story.

Drew: So it’s funny, I think every salesman in the world, whether they’re CEO or just says, “If you marketing or just get me in the room, I’ll be able to close.” But we know that’s not true, because otherwise, you know, all these businesses would be healthy. But the close rates that a lot of the companies that I talked to are, you know, maybe 20% one in five, because that’s what they’re asking for coverage from the marketing is 5x coverage. It’s like crazy. So there’s a problem there that either they’re talking to the wrong people or that or the product isn’t as competitive as they think it is, or the messaging is wrong and it could be any combination of those things.

So you have three P’s. One of those P’s is persona. Our group knows what that means, but maybe there’s some thought that you have in terms of defining persona that will either remind us of why these are so important or something that you’ve seen where people miss out on their persona definitions.

Allyson: Yes, perfect. Well, having a clear idea of who you are talking to and who you are trying to motivate to take action becomes the filter for all of your messaging decisions. So oftentimes, a company will say, “Can you take a look at my website and tell me what you think?” And my first question is, “Well, who are you talking to? Who are you trying to motivate to take action?” And it’s the same question I would ask for a sales deck or an article or anything else. I can’t tell you if it’s good unless I know who you’re trying to talk to. And then I need to understand their thinking. I need to understand how they’re approaching decisions around solutions like yours. 

So I think about five elements of a persona. The first is pains. So what are the key challenges and pain points someone is facing today that they need to overcome? And it’s functional pain points. So what are the jobs to be done that any solution needs to accomplish, but it’s also emotional and social. How are they feeling today that they just can’t stand anymore? And social is, how are they being perceived, but also, how is their pain impacting their relationships today? So when you understand that, you are much clearer on what you might say to someone to show that you empathize with where they are, or to call out, “Hey, we know you need to solve these things. We can do that.” So that’s the first one.

Drew: Let me stop you for a second. I want to just put a pin in this, because we had Chris Voss, “Never Split the Difference” author. And one of the keys in negotiating is also being aware and having this empathy for the person that you’re talking to. It looks like you’re having a bad day. Talks about that as one of the entry points, and it feels like that is so obvious, but I know that sales in particular is ready to get into this thing. And here’s all the rational thing, but sometimes it’s just, “Hey, we gotta connect with humans on a very personal level.” 

Drew (AD Break): This show is brought to you by CMO Huddles, the only marketing community dedicated to B2B greatness, and that donates 1% of revenue to the Global Penguin Society. Why? Well, it turns out that B2B CMOs and penguins have a lot in common. Both are highly curious and remarkable problem solvers. Both prevail in harsh environments by working together with peers, and both are remarkably mediagenic. And just as a group of penguins is called a Huddle, our community of over 300 B2B marketing leaders huddle together to gain confidence, colleagues, and coverage. If you’re a B2B CMO, why not dive into CMO Huddles by registering for our free starter program on CMOhuddles.com? Hope to see you in a Huddle soon.

Allyson: As products evolve over time, it’s surprising how many times you think, “Well, why does this new feature matter?” And does it actually solve a pain point that is top of mind or urgent for your ideal customer? And so you end up going back to this pain section a lot to see, even as a filter for what you should prioritize on your roadmap, like, is it actually important to your ideal customer? 

The second is gains. So where does someone want to be after they’ve solved this problem, what jobs will be done, or what will they have accomplished in their company or in their lives? But also, how will they feel? Relief, hope, optimism, success? And then how will they be perceived, and how will their relationships be impacted? And you know, in my last role at Handshake, we helped employers understand that the way they were recruiting college students was not working today, and they were often feeling it. They couldn’t make their numbers. They weren’t hiring a diverse enough class. The persona was feeling very exposed and realizing their job was potentially on the line if they couldn’t get their early talent recruiting program in order. And so at the end, they wanted to not only have been able to recruit from more schools and hire a very skilled, diverse set of talent, but they wanted to feel confident. They wanted to feel relief. They wanted to be perceived in a different way. So that impacted what we emphasized in our messaging.

And then the last three components of the persona to touch on: Those are shifts. So what changes in someone’s life to be open to the solution, to be considering something new? It could be a series of events precipitates it. It could be something in the company has just been out of whack for too long, and now the CEO is taking notice and pressuring a team to get something in order. But what are the likely shifts that have happened? And then what are the blockers? So even if someone knows they have a problem, what is going to stand in their way of taking action? And this could be the attractiveness of other solutions, but it often comes down to budget, mindset, change aversion, difficulty getting other stakeholders on board. What are those blockers? And then finally, what are the motivators? And this is a great hint for what you need to be creating content around. Will this person be more motivated by customer success stories, by data, by relevant case studies of similar companies to theirs having great success? And so proactively addressing the blockers and creating content that will motivate this group are just some of the great insights and action steps that will come out of creating a persona like this.

Drew: One of the things as we’ve had Brand Adamson with us several times, and he always talks about how the gain of change has to be greater than the pain of change. So that’s sort of one in this conversation. It feels like, right now, it’s extremely difficult in all of B2B to get people to buy. They’re pushing off buying. You know, they’re buying slower. So often people are losing to no action, more so than they are to a competitive thing. We have a question on this – it’s really a challenge. So enterprise sale, 14 people on the buying committee, a CFO over here, maybe a business unit operator over here, probably an end user over here, and they all have different triggers and blockers and motivators and so forth. But we also know that you can’t make a completely different message to every single one of them, because then they don’t, you know, they don’t realize they’re buying an elephant. They’re just buying a tail, or they’re buying a foot. That old analogy there. So how do you manage this, and going back to not splinter your content so that you have absolutely different story for the CFO versus this one? How do you find that thread? And what’s, you know, because it could get matrixed and problematic fast.

Allyson: It can, and that fragmentation is your enemy, that it just creates so much complexity and slows the team down. So a few tips here. The first is, even if two people on the buying committee, on the surface have very different job roles, seem to have different needs, but the same messaging resonates with them, then use the same messaging. Don’t create new messaging just because they are a different person in a different role, so that might simplify some things. The second thing is, I would try to narrow to the most minimal number of different personas and messaging frameworks you need to create. And then do create the persona for each of those, and one by one, create the messaging framework. We’ll talk more about what that entails, but the persona and then the key messages that will appeal to that person. And then think about the essential content that you can create for that buyer. So many times, your homepage should appeal to the primary buyer, that’s the person whose attention you catch first, and you’ll be driving them there to get more information. But maybe these additional personas get their own landing page if you have enough information for them. And then oftentimes you’re putting content in the hands of the primary buyer, who’s then going and sharing that content internally. So what can you equip them with? Or to the extent I work with many companies who are trying to get on the radar of the executive leader, who is the ultimate decision maker and approver, as well as this internal champion, and in that case, you do need to create two sort of separate content motions to move that person forward. But my biggest advice is, yes, differentiate. You do not want to combine messaging and water it down, because then it won’t appeal to any group. But keep it as simple as possible, and only add the next set of messaging if you’re finding it’s blocking the sales process. That’s when you’ll know, okay, it’s time to add the third or the fourth.

Drew: There are several things I just want to repeat, and maybe reframe slightly that I heard. So we’re making buying easier because we have this one primary advocate, and we’re anticipating all the questions that everybody else might ask them, whether it’s the CEO or the CFO. And by anticipating those things, we’re equipping this person to be your champion. And as I like to describe it, the speed-to-hero opportunity increases because you’re making it easier for them to sell internally. I also think about your happy path, and I’m imagining that there are certain things in the happy path that may be more important to the CFO versus the other one, and so you just have to identify those things, whether it’s like a buyer’s guide or an ROI calculator, those things. And then the last thing I just want to comment from our Huddles community, there’s at least one CMO who creates tiger teams, war rooms, and then virtual sort of pages for the primary buyer, which assembles all that stuff in one place for them. So it’s like their own private intranet where they can find all those pieces. Oh, you need this for your CFO, here it is. So that person doesn’t have to hunt around. So now we go to your next P and we’re covering a lot of ground, and we have more to go. So you’ve got positioning and personality. Let’s just quickly sort of summarize maybe a real-world example of positioning.

Allyson: Perfect. So positioning is really about, how do you make it clear how your product is different and better than the alternatives, which might also be very valuable solutions, but you want to show that those other solutions are not the right choice for your ideal customer, yours is the best choice. And so if you think about the starting point, there’s a reason that your ideal customer is choosing your competitors. So get clear on what’s putting that product, or those products, in the upper right of a positioning matrix, if you think about a two by two. And as an example, QuickBooks. QuickBooks is the 800-pound gorilla in the, you know, accounting software space if you want to do it yourself, and the reason is because it’s incredibly automated. They call a lot of the workflows, auto-magic. You input a minimal amount of data, and all of your reports and books are filled. And they also have an incredible accountant network, so you have this real safety net of experts that can come in and help with any challenging situations. But then, if you are a company that is a challenger and taking on these alternatives, you need to think about, how can I flip the matrix? What are the attributes that would put me in the upper right corner and put the competitor, QuickBooks, lower, in a less desirable position? And I find that the four categories of things that tend to help you flip the matrix are either saying you are better for a specific segment of customers, so yeah, QuickBooks is for all small business owners. We are for a very specific segment, and this is what that looks like. The second is saying you are better for a specific use case. So sure general accounting go to QuickBooks. But if you just want invoice management as an example, the best place to do invoicing is through our software. And the third is benefits, so you actually do get extraordinary benefits, above and beyond what the alternative does. And the fourth is better user experience. And you have to be careful with this one because this is just our features are better, but sometimes the ability to use the product is so much easier and better than the alternative that does set you apart. So I’ve worked with a number of startup accounting software companies, and one focused on the specific segment plus use case. They were very specifically for solopreneurs, many times, who were in their second act, and so they were optimizing for retirement savings, long-term wealth. And so this software claimed that they were the best at tax deductions and retirement savings planning. You can probably do that in QuickBooks, but they’re not talking about it all the time. So that really helped attract a certain segment. Another company was for people who didn’t want to DIY, but also didn’t want to go through the hassle of recruiting their own accountant, and how would they even know if that accountant was the right fit? So there was a team of accountants. You sign up, we will match you with the right person, and that helped them get traction in the market. So those are some tips for thinking about what is it that makes our product that we can emphasize in sales conversations and on our website that make our products so uniquely better, and it’s surprising how many companies make customers work too hard to figure that out. So make that differentiation really, really obvious.

Drew: So vertical use case benefits and UX as four possible ways of positioning yourself against a competitor. What I love about that is you got to pick one and or two, because the definition of strategy is knowing what you say no to. And I think, where strategies fall apart, and that’s Peter Drucker, I think, is when you’re too broad, you’re everything to everybody. That’s not a positioning and so positioning is, say, accepting the fact that you’re not right for everybody, but you are really right for this vertical market in this use case. And I wonder, funny, UX is in that whole customer experience thing is, lots of brands want to be there, want to say, we have the best service, but it feels like of the three, it’s the hardest one to win and the hardest one to prove without your customers saying it for you.

Allyson: Right. I would say at Thumbtack, that is how we tried to differentiate because it’s a marketplace for local service providers, and the outcome is the same, no matter if you ask your neighbor for a recommendation of a plumber, or you go on Thumbtack, or you go on Yelp, but we tried to say we have the best directory with all the reviews and customer comments you need and transparent pricing. So the “how” you decide is better for the right type of person. But I agree it is one of the hardest, and this is, by the way, why you have to figure out your persona first because this is product positioning, and you need to position against the alternatives that your person will actually compare you against. So this is another place where you can simplify. You don’t need to compare yourself to all of the potential solutions out there. It’s just the ones that your ideal customers will be comparing you against, and then you need to get very clear on how you talk about that differentiation to them.

Drew: And famously, picking one enemy is so much better, because it really makes it clear to the organization we’re gonna beat these guys. And that really is a wonderful tool and it’s worked over and over and over again when you know who the bad guy is or the enemy. We were going to spend a fair amount of time on archetypes and persona. I want to make sure that we cover value prop because I feel like folks get this wrong. So let’s come let’s do that, and then maybe we’ll have time to come back to sort of positioning and personality. But let’s go to value props. What do you mean? And what’s a good value prop look like?

Allyson: When I think about a messaging framework, doing your persona positioning and then personality work leads to you being able to create a summary of your messaging which starts with a unique selling proposition, which is your headline. We are a what? So, what category for who? What ideal customer that delivers? What big outcome, what is the big promise that transformation statement through what key differentiators? And these differentiators are usually the biggest benefits of using your product. It’s why someone should choose you over the alternatives.

So value propositions, I then like to create three value propositions that support this USP, and these are benefit statements that explain the top benefits of using your product. They tend to start with a benefit and a “so what?” For instance, I’m working with a company now, and their platform helps you respond blazingly fast to emails to accelerate pipeline. Like just responding quickly sounds helpful, but then spell out the “so what?”

When you think about crafting value props, there are a few characteristics. Many times they start with an action verb, like quickly, smoothly, simply, whatever it is – some way of saying, accomplish this thing in a better way, or with a modifier: best, fastest, something that really speaks to the heart of that benefit. The other thing about value props is they’re explaining why the features of your product are useful and the end result that they’re driving.

I like to think about your value props as being three buckets for your different features. Think about the top functionality of your product. Which of the value props do those features support and enable? This is a good gut check. If one of your key features or workflows is left out, like you haven’t spoken to the value that delivers, it doesn’t fit under one of your value props, then you’re probably missing something. So you need to go back to the drawing board, or if you find that they’re all clustered under one, then something else is off. You want your features to be equally distributed, and this actually helps your messaging framework have some durability, and really helps your customer base understand the value of new things you launch.

Many times, your new features will further support one of those value propositions, like doing something faster or accelerating revenue or simplifying a process. Two other things to emphasize: they need to be differentiated. If you could copy and paste your website with your value props onto a competitor and it would describe their product, then your value propositions aren’t differentiated enough. So they need to emphasize these different benefits, and you want them to be defensible. In the spirit of durability, thinking about these value props lasting at least a year or so, you want to make sure that you’re thinking ahead, and these aren’t the things that your competitors are likely to launch a couple of months from now and chip away at that differentiation.

They need to do a lot of work, but this is a great place to spend time, and I’ll tell you, if you go through the persona and positioning process, these will likely jump off the page at you. It will be so much easier to know what you need to emphasize.

Drew: Can you give a quick example of “where the company for blank and blank” that is differentiated in this way?

Allyson: Sure, I can use Handshake as an example. For college students, Handshake is a recruiting platform for college students. Or really, the job app for college students to get hired. So that’s the big promise. It’s not “search for jobs.” It’s not “talk to employers.” The big outcome is to get hired by connecting directly with employers hiring college students, having basically a content play, content that helps you decide which job is best, and by having events and tools to put your best foot forward, essentially.

I’m botching those a little bit, but the structure here you see, we’re promising you’ll get hired, but the way you’re doing that is we’re connecting you with the right employers. We’ve got content to make that easier, to educate you and help inform your choices, and you’ve got events and great, rich profiles and other things that you won’t be able to find on other platforms that make it more possible for you to get hired.

Drew: We’re the resource to help college kids get hired. It’s funny because, you know, coming up through packaged goods, it was “to convince blank to do blank instead of blank because of blank.” And so it was “convince mouthwash users to use Listerine instead of Scope, because Listerine was more efficacious.” And then there’s these are the three ways, right? Boom, boom, and boom. And it really helps when you can get it down to as short a sentence as possible.

You know, one of my favorite essences of that was Gain detergent and their positioning line was “smell as proof of clean.” That was internal, if you smelled the clothes that was proof of cleanliness, and that’s still their thing 50 years later. Now they execute that in a lot of different ways, and you talk about a visceral reaction, right? What do people do? What do people who really care about clean clothes do? They smell it. And so it’s just a brilliant one that they could defend over and over and over again. Very few B2B brands have that kind of simplicity.

Allyson: Well, and I can give the B2B side of Handshake. You know, Handshake is a recruiting platform for employers hiring entry-level talent through better data, better tools, and access. You know, it still works on the B2B side as well. And when you get this right, I agree with you, Drew. The simpler and more repeatable, the better. So this should be in your brand personality, but more casual conversational language. It is likely in the hero module of your website. It is the first thing your CEO will say when they’re in broadcast media or talking to a reporter, and they say, “So tell me what is your product.” It just becomes the go-to first statement, and then it also alludes to the value props, and you’ll talk through those three big benefit buckets that differentiate you. So it’s a really helpful structure.

Drew: I love it. There’s so much I wanted to cover, and we didn’t get to archetypes, which I love, and any of the brand personality work, but that’ll be for another time. So if we wanted to wrap up with two do’s and one don’t when it comes to use the term irresistible marketing?

Allyson: Yes, okay, so I’d say first big do is plan around the customer journey. It’s such a simple framework, but the content you need to create to motivate someone to take action or to break through, and the channels you use are totally different if you’re trying to attract someone, versus nurture or convert and then onboard and engage them. So plan around the customer journey and even a red, yellow, green type dashboard. Where is there friction in the journey for our customers and or where are we underperforming? Can help give you a sense of where you need to put a lot of your marketing energy.

The second, I’d say, is do get comfortable iterating on messaging, and anytime you feel like your messaging is off, first, go back to the persona and positioning, and then rework that framework.

And third, don’t let marketing and sales get misaligned. It will create customer confusion. It will create internal tension and chaos. And alignment on persona, positioning, and messaging is actually a great foundation for those teams to be very aligned.

Drew: Alright. Well, Allyson Letteri, author of “Standout Startup,” here’s the book, just again, I really found it so useful just to frame this and keep it simple. How can listeners engage with you?

Allyson: Well, you can go to my website, and I do have a great guide on how to create messaging that steps you through this process again. So AllysonLetteri.com, backslash resources, please connect with me on LinkedIn, and then please pick up the book if you want a deeper guide to get through this messaging process, “Standout Startup.” And thank you so much, Drew. 

Drew: Thank you.

If you’re a B2B CMO and you want to hear more conversations like this one, find out if you qualify to join our community of sharing, caring, and daring CMOs at CMOhuddles.com.

Show Credits
Renegade Marketers Unite is written and directed by Drew Neisser. Hey, that’s me! This show is produced by Melissa Caffrey, Laura Parkyn, and Ishar Cuevas. The music is by the amazing Burns Twins and the intro Voice Over is Linda Cornelius. To find the transcripts of all episodes, suggest future guests, or learn more about B2B branding, CMO Huddles, or my CMO coaching service, check out renegade.com. I’m your host, Drew Neisser. And until next time, keep those Renegade thinking caps on and strong!