Episode #233:
Ken Rutsky explains why teams often confuse what they do with the problem they solve and how that confusion creates misalignment and weak differentiation. He shows how to define an issue that is big enough to matter yet credible to win, then use it to guide narrative, segmentation, ICP focus, pricing, and the proof of concept experience. The result is more precise positioning, more substantial alignment, and higher conversion.
“Obsess about the strategic big problem that you solve for your customers, and get in alignment about why you do that uniquely, how you do that uniquely, and why it matters.” – Ken Rutsky
In this conversation, Ken unpacks practical ways to listen and lead, replace feature talk with problem-led storytelling, and say no to off-ICP deals. He shows how a shared problem thesis unites marketing, sales, and product, and how simplifying the buying experience turns alignment into measurable revenue impact.
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[Transcript]
[00:00:05] Steve MacDonald: Welcome to the C-Suite Sales and Marketing Perspectives podcast. I’m Steve MacDonald, your host, and today we have a very special guest on Ken Rutsky. Now Ken, you are a five-time B2B CMO. You’ve been around the block a few times. You got a few things to say, which we’re going to get into today, but you’re also a published author.
[00:00:26] Steve MacDonald: You’ve been a consultant. You are actually an avid cyclist, and I’m going to have you explain that a little bit, ’cause you said you were a gravel cyclist, and I had never heard of that before. I’m like, how did I never hear of that before?
[00:00:36] Ken Rutsky: Yeah, I’m surprised ’cause it’s like all the rage in cycling for the last probably six or seven years, which is basically people want to get away from cars and explore more, but they want to go fast.
[00:00:47] Ken Rutsky: So, you know, take the curvy handlebar of the road bike, but they put a bit, a little bit of a fatter tire, a little more softer variety, and you go on fire roads and gravel roads and dirt roads, and a little bit of single track like a mountain bike. And so I do that and road bike and ride probably three to five thousand miles a year.
[00:01:06] Ken Rutsky: That’s where I do all my best thinking and get away from the hecticness of both career and family life. So that’s my peaceful time.
[00:01:14] Steve MacDonald: Well, I can understand that. I jog, and that’s when I do my best thinking. And you and I are very parallel in our family lives. You’ve got four kids. Three of ’em are out of the house.
[00:01:24] Steve MacDonald: I’ve got two that are out of the house, two on the way. So we’ve got a lot in common, but our shared passion around this topic today, which is about how do we literally transform our go-to-market strategy by solving the right customer problems? And that seems like such a basic thing to say, right? We all obviously know the customer is the hero, the customer is.
[00:01:48] Steve MacDonald: None of us are going to say we’re not customer-obsessed or customer-focused, and we’re always solving their problems, but we’re going to break that down to the problems that exist and get in our way to do that inside of our organizations, right? But I already said a lot, but I want to make sure that I give you just a moment to expand.
[00:02:10] Ken Rutsky: You know, a long time ago, I wrote a blog called The Problem with Problems. It’s so old I can’t even find it anymore. But when I workshop, when I was consulting, which I was doing for more than a decade prior to taking my current CMO role, one of the first things we would do is we would workshop the problem, and I would simply ask a group of executives, typically in smaller startups.
[00:02:31] Ken Rutsky: So you would think there’d be more alignment, right? Like what is the big problem that you solve for customers? And at the end of that, and I would just say, give a few examples, right? I’d say like for manufacturing companies that have to improve profit margins yet are faced with rising costs and can’t control them.
[00:02:53] Ken Rutsky: That’s a problem, right? Or someone who can’t do something. And I would show an example or two and I’d say, okay, now everyone independently write down a problem statement. And then we go through those, and at the end of it, inevitably, I almost said this without even thinking. Congratulations, you get the same score all my other clients do, which is a C minus.
[00:03:13] Ken Rutsky: Now it’s kind of a little bit courageous to say that in front of them because this is the first workshop usually that I’ve done, and I only maybe know the CEO or the CMO. And to say that, you know, grade them as a C, as an executive team, first thing you ever do. And I say, but it’s okay because that’s how everyone does.
[00:03:30] Ken Rutsky: And there are really three mistakes I think that people make. And the first one, which is the biggest one, is they confuse what they do with the problem they solve. So we create great, you know, glasses with perfect prescription acuity and thinness versus we help people see without weighing down their faces, right?
[00:03:55] Ken Rutsky: So, you know, what is the problem versus the solution? That’s the first thing, I think. The second thing is they either aim too high or too low. And that metaphor I like to use on this is they either say we solve world hunger, or we sweep the crumbs off the table. The first one nobody believes because very few people have the credibility to solve this massively huge problem.
[00:04:18] Ken Rutsky: And then the second one is like, nobody cares ’cause it’s so small. So it’s finding that sweet spot that just right is kind of like, you know, the three bears, right? This bed is just right. It’s not too hot, not too cold. Maybe we solve the problem of how to feed low-income children who don’t have stable home lives in the tri-state area.
[00:04:40] Ken Rutsky: You know, you get specific, but still, that’s a big problem, but it’s not so big that it loses credibility. So what you want to do is you want to go to your customer and say, the problem we solve for you is something that’s big enough for you to care about, but you’re not going to just laugh me out of the room.
[00:04:57] Ken Rutsky: Right, you know? And I do a lot of work with cybersecurity companies, and I’ll let this company remain nameless even though they don’t exist anymore. And I did some work with them. They did great. They got an IPO, you know, they got rolled up into another company, great liquidity for all the shareholders, and then they decided their slogan was reinventing security.
[00:05:16] Ken Rutsky: That’s when I knew they were heading into trouble because what does that mean? Like it’s just so big. And so this whole thing of getting into that sweet spot of a problem that matters, but you also have the credibility to solve. The third thing is they just don’t know, and they all have varying views.
[00:05:34] Ken Rutsky: You get five people, you get six different problem statements. Now usually you can tease out a problem from those. If an executive team has yet to even articulate the problem they solve, you’ve got a problem right there.
[00:05:45] Steve MacDonald: Oh, you got a big problem. In fact, it’s interesting because we only have C-Suite executives on the podcast, and I ask them all the same question.
[00:05:54] Steve MacDonald: Well, we prepare for what we don’t want to talk about, and I ask them, what are their two biggest challenges for creating long-term sustainable growth? The number one challenge that they state, and it’s 70 plus percent of all C-Suite executives say this, their biggest problem is internal alignment. So what you find, which is massive misalignment amongst the C-Suite, they know it, right?
[00:06:22] Steve MacDonald: They know it. But the bigger problem is what do we do about it? And I think that would be a great way to kind of segue into our like, okay, get the problem. We have a problem defining our client’s problems, right? Or our customer’s problems. How do we start by solving our own problem, that misalignment?
[00:06:43] Ken Rutsky: I think a lot of this comes down to, you know, kind of just common sense of communication and getting it out there.
[00:06:49] Ken Rutsky: So keeping the same, you know, kind of thread going about the workshops I would do is once you get everyone talking about it, you actually find a lot of commonality, but it’s just articulated in different ways and not in a way that’s going to be powerful in the marketplace. So I think getting it out in the open and debating and coming to consensus, you know, I always like to say better be 80% right and in agreement than 100% wrong with three people not agreeing at all.
[00:07:18] Ken Rutsky: Right. So I think you’ve got to be willing to have those tough conversations that really tackle these kind of tough issues.
[00:07:26] Steve MacDonald: Yeah, absolutely. It’s interesting, and I want to ask you about this because you and I talked a lot about listening to the customer, and there’s data that we can listen to. There’s actual customers themselves, right, and conversations like we’re having right now.
[00:07:45] Steve MacDonald: Because the one thing that everybody, when I talk to them, agrees that when they talk about misalignment in the C-Suite, the thing that brings alignment is the voice of the customer. They’re the highest authority. It’s their problem we’re trying to solve. How do we bring in information from the customer—their voice, their wants, their needs, their desires, their problems—instead of just being people that have risen to the C-Suite ’cause we’re smart, we know how to make decisions, that we can do it on our own, we’re independent, right? That gets us down this misalignment path. How do we use the customer to bring that back together?
[00:08:28] Ken Rutsky: Yeah, product development, they have this problem statement they talk about, listening to the HIPPO, which is the highest paid person’s opinion. If you could actually answer highest paid person’s opinion, right, and like when you’re in this group setting, you have that C- executive say something, right? And it’s like it’s not debated because that’s the highest paid person and how dangerous that is in your product roadmap. I think the same goes for not listening to the customer.
[00:08:53] Ken Rutsky: You have to listen, but you also have to lead, right? So this is not just a listen to your customer, because customers—you have, Steve Jobs proved this if anyone did—customers have a very incremental view of the future. And I’m working with a lot of startups and worked in a lot of startups. And startups are about changing the trajectory that a customer can go on.
[00:09:17] Ken Rutsky: And so when you get into the solution space, customers expect things to move from here to here. If you want to take ’em to here, then you really have to connect to the problem, not the feature set or the way they expect to solve it today. And so there’s an art of listening, and there’s also an art of storytelling that gets them to, you know, when you start with their context, right?
[00:09:41] Ken Rutsky: Context is everything. So when you start with that customer’s context, you almost get permission. It’s kind of challenger sale, right? You get permission because you bring insight into their world, not insight about your world.
[00:09:54] Steve MacDonald: Which is what we do, right? And I have to say, I’m a two-time SaaS founder myself, right?
[00:10:01] Steve MacDonald: And you can’t help it—you fall in love with your product. You fall in love with the tech, right? You’re like, oh my goodness, as soon as people just understand what we’re allowing them to do, the floodgates are going to open up, right? It’s not true. I’m launching an MVP next month, and I fight against that mentality every single day, right?
[00:10:27] Steve MacDonald: I just have to tell them the feature set that’s inside of here, and they’re going to go, oh my gosh, Steve, you’re the best thing ever, right? How do we get away from the product-feature problem-solving mentality and move to what you are talking about—making them the hero of the story? That’s a very different mindset.
[00:10:50] Ken Rutsky: Yeah, I think there’s a structural clue here, right? And it starts with what is the story you’re telling, to your point, Steve. And, you know, the story I always want to tell is how I’m going to transform my customer’s world from what it is today to a better reality, right? And you notice, like, I never said anything about the product.
[00:11:12] Ken Rutsky: That statement, like, so, you know, the beginning of the story is you live in this world. The end of the story is, look how much better this is for you professionally or as an organization, or ideally both, right? So I’m going to take you from this state to this state. Now, the reason I can do that is because your current, again, in the context of a problem, I’ve got this problem that I’m going to solve for you and in your world today, I like to use this like—
[00:11:40] Ken Rutsky: The world today, the air is very smoggy, and the problem is your kids have asthma. Right now, I don’t have the power to make the world not smoggy, but maybe I have the power to let your kids breathe easy. And so if the story I can tell is in today’s world, where the air is polluted everywhere and you’re afraid to let your kids go outside because they have asthma, I can free them to play on the playground.
[00:12:04] Ken Rutsky: Would you like to come on that journey with me? Nothing about how now I say, okay, and you know, now the customer says, “But we tried this, we tried that, we tried this.” And you know what? I get that because most of the customers I talk to, and this is where listening to the customer and learning deeply about their problem, most of the customers we talk to who deal with this problem try A, B, and C.
[00:12:27] Ken Rutsky: However, the unsolved challenges or the, you know, met opportunities, right? This old fear and greed that the things that you can’t solve the old way are these, the things that you miss out on, these benefits, are these. And so, if you try the old way, you’re still going to be stuck in the old results. Now, what if you thought differently?
[00:12:49] Ken Rutsky: Now I can take you from A to B. The ways you’re trying to get to B don’t work for these reasons. Now let me explain the way I’m going to take you there. And by the way, maybe it’s not me, it’s any product or solution that has these characteristics. I talk about this as being an approach, innovation, and mindset, but it really starts with mindset.
[00:13:11] Ken Rutsky: We thought about the problem differently, and this is where I’m not a biology person, so my metaphor is going to fall apart. We didn’t attack the lungs, we attacked the brain, or we realized that asthma was triggered in the brain. This may be totally untrue. I mean, so I may be making stuff up. I do that. But you know, rather than attacking the symptoms or this, we went after this unknown cause that we discovered.
[00:13:34] Ken Rutsky: So if you had the mindset that the problem is here instead of here, or the problem is this instead of that, then you would take a different approach to solving the problem. And so, if you take this approach, in order to do that approach, you need to build these innovative technologies. Well, guess what?
[00:13:51] Ken Rutsky: That’s exactly what I’ve got. I’ve got these innovative features that allow me to take this approach because the way I thought about the problem that I’m solving for and taking you to that better place is different than everyone else. If you have that magical gift, I could make you a hero because I can change your world.
[00:14:09] Ken Rutsky: I can make your kids healthy, I can make your company more profitable, I can make you a more successful executive. And so, taking people through starting and ending with the problem and the transformed state, and then filling the middle two chapters, the gap in the current solutions and the innovation in the way I think differently.
[00:14:29] Ken Rutsky: In that top left, that was all written. By the way, if you want to dive into this, you just get my book Launching to Leading. I call this a viewpoint story, half the book right there.
[00:14:38] Steve MacDonald: So let me tell you a story that accentuates exactly why what you’re talking about is so important. So, another three-time B2B CMO came onto the podcast, and she said, “Steve, you can’t say this publicly.”
[00:14:54] Steve MacDonald: She said the name of the company. She said their SaaS company. They went after their jaw-out-in-the-dark, you know, shoot-for-the-moon client, right? And they got into an RFP and they got into a presentation, two-hour presentation, okay? And the entire two hours, they never talked about themselves. Not once. But the client, who hired them by the way, was so enamored that they understood their business, where they were, where they needed to go, what the challenges were.
[00:15:28] Steve MacDonald: They didn’t care about the actual way you did it because they demonstrated that they got their business, their lives, their challenges, their problems, the way nobody else did. Therefore, oh, you’re going to have a better solution, obviously.
[00:15:46] Ken Rutsky: And you know, it’s so easy to compete away technology and words, but what’s hard to compete away is an approach or a mindset, right? So, if you were truly innovative, you’re thinking about the problem differently for your customer and approaching the solutions differently, and then other people could kind of say, oh, we got that feature too, we got that feature too. But they don’t really fit together the same way.
[00:16:07] Ken Rutsky: They don’t really approach it the same way. And by the way, they don’t even think about the problem the same way because they’re stuck in the old way of thinking. And that’s where, you know, I talk about, the other thing I’d like to say is, you know Jim Barksdale, who was the CEO of Netscape when I worked there, probably the best CEO I ever worked for.
[00:16:24] Ken Rutsky: Yeah. Jim was an old southern gentleman from Mississippi, and he had all these like down-home sayings. And the one that really sticks with me forever is Jim said, “In the battle between the bear and the alligator, the winner’s determined by the terrain.” And he said, “So if you’re a bear fighting in the forest, don’t get in the swamp.”
[00:16:43] Ken Rutsky: And a lot of B2B marketing, and I think B2B alignment, is around aligning around the problem set and the customer set that are in your terrain, where you’re going to tilt that playing field to you so that you get there and you tell the story, and your competitor’s just on their back feet the entire time because you’re in the forest and they’re drowning, or they’re an alligator and they can’t get up in the tree.
[00:17:07] Ken Rutsky: Right. So, no, it’s really about creating the context for the conversation and the knowledge around the problem, to your point, and the customer. Then also, I think the last thing is, you know, very few organizations are big enough or have scale enough to solve problems for everyone. So, understanding your ideal customer profile, the segments you operate in, who share that problem, who you can actually take on that journey, versus trying to take everyone in the world on that journey.
[00:17:38] Ken Rutsky: Is another huge alignment thing that I think organizations have a hard time with. The CRO, you know, the head of sales, like if he has an opportunity, they want to close it. If their VP of Product is being told, you’ll build this ’cause they’ve got a deal based on it, she’s often forced to build it, even if it’s a one-off that won’t get you further.
[00:17:58] Ken Rutsky: And so, saying no and taking your thought is so critical, and that’s where I think alignment really gets put. It’s hard to maintain because the deal on the table always looks like we should get it until it doesn’t.
[00:18:13] Steve MacDonald: But that deals on until you such an important point, and I’ve talked to a lot of CROs about this — the power of no. Because if you don’t have a really tightly defined definition of your ideal customer profile — and by the way, that ideal customer profile is what your entire organization should be set up to serve.
[00:18:33] Steve MacDonald: If you bring in deals that aren’t right in the middle, but are a little bit over here or up here or over here, A) they’re going to churn, they’re going to ruin your NRR, they’re going to eat up resources, time, expenditures. They’re going to take you down rabbit holes you never should have gone down. You regret those decisions. So I love the analogy — I’m going to use it.
[00:18:56] Ken Rutsky: Yeah, I always think it’s better to win eight out of ten and compete in ten, than compete in twenty and win four — or even win eight. Even if you can win eight out of twenty, you’re not competing in ten more that you could win. So you should be winning sixteen out of twenty if you’re choosing right. Now, some markets are small, some are growing that fast.
[00:19:16] Ken Rutsky: You know, there are a lot of dynamics at play here. But at the end of the day, knowing your customer, knowing your value, and connecting your value to the segment of customers that the problem matters to is really how you win more than your fair share.
[00:19:31] Steve MacDonald: So here’s my takeaway from this whole portion of the conversation — when we go after those deals that aren’t quite ideal for us, but they’re so tempting because A) we’ve got a quota, and we’re going to be meeting with the board in a couple of weeks. And the first thing they’re going to say is, “What’s this quarter’s quota look like? And what’s next quarter look like?”
[00:19:51] Steve MacDonald: So it’s so alluring and enticing to do that. That’s taking us as bears and putting us into the swamp to compete. It’s taking us out of our natural habitat where we’re going to thrive. I love that analogy — I am going to steal that analogy, I’m going to use it a million times. So let me ask you this.
[00:20:15] Steve MacDonald: Because one of the problems with focusing on the features as the problems themselves, or the solutions to the problems, is that — like I had this articulated to me — a gentleman that came on the podcast, again, he’s a Chief Customer Officer. His ICP was CISOs — Chief Information Security Officers. So he was talking with a CISO, and that CISO had just purchased an important part of his tech stack.
[00:20:46] Steve MacDonald: And he said, “We looked at fourteen different companies. We put an RFP out.” And he said, “Steve, every single one of them came back, and all ten parameters that their product had to meet in the RFP — every single one — check the box, we do it.” It’s this sea of sameness.
[00:21:00] Steve MacDonald: If you compete on product, especially with ChatGPT writing code now and everything, the fact that you’re going to compete on product and feature set — even if you came up with the most innovative feature set — it is a short-lived differentiation strategy.
[00:21:19] Steve MacDonald: So getting in there and competing on that level is… competing, and you can see the prospect’s eyes start to glaze over as you become part of this haze of product features that are out in the market that they can’t really put their finger or their thumb on. And to differentiate, you put yourself into the crowd.
[00:21:43] Ken Rutsky: And usually there’s one person who drives it. Like there’s one vendor who’s the guy — you know, Chris Lochhead and that whole group in category creation will tell you, you know, the category king wins 80% of the spoils. So you’re one of the 20% chasing. You get what I call stuck in launch — like you’re always launching the next feature, and it’s always the next feature that’s going to change the dynamics.
[00:22:04] Ken Rutsky: And it’s the next thing, the next thing. And yeah, you’re in this endless loop of “feature, feature, feature, feature.” “Oh, if we just have this, if we just have this,” versus saying, “Look, you know, I can’t compete again in 100% of these deals, but I can compete in 20 of ’em really well. Now, what do I build?”
[00:22:23] Ken Rutsky: What problem do I solve in a differentiated way so I win nine out of ten of those?” And so again, you know, it’s niching down, it’s focusing, it’s understanding where you are in the market. Because you know what? If you are that person at 80%, it might make a lot of sense for you to just turn on the feature factory and just keep cranking it out — just add another smidge of value, another smidge of value.
[00:22:48] Ken Rutsky: Because nobody can keep up with you and you’re the default purchase anyway. As always — it depends.
[00:22:54] Steve MacDonald: So here’s what I’d love to get your point of view on. Everybody says in the world of B2B and an ABM go-to-market motion, it’s all about relationships. It’s all about building those relationships and founding them on trust, right?
[00:23:09] Steve MacDonald: So feature sets don’t build relationships. That same CISO that evaluated fourteen companies — you know what he said at the end? He said, “Here’s what I wanted to know. I just wanted to know what it’s going to be like to work with you — the experience of working with you if I hire you.” It wasn’t the feature set — it was about the people.
[00:23:27] Steve MacDonald: It was about what it’s going to be like — our teams working together. Is it going to go well? But we talk about service a lot in SaaS, right? We talk a lot about service, and it’s very important. It’s a key part of the CX strategy, right? But tell me a little bit about the relationship side of this and where it comes into play.
[00:23:49] Ken Rutsky: Yeah, I mean, I think you have to wind this back through the whole thing. So I make a choice in the market that I compete in. At Aryaka right now, there’s a lot of POC — proof of concepts — that have to happen because it’s deep networking and security infrastructure. And so people want to actually see it work in their environment. That customer experience, the POC, is really a key determinant of winning the business or not, because you’re with them. And if you’re not with them, how you are with them in a proof of concept is going to indicate how you’re going to be with them as a supplier in a purchase relationship.
[00:24:07] Ken Rutsky: But it goes back beyond that. Now, I think back into the marketing — what’s the experience that the customer has from the first time they make contact with you? Are you seen as listening? Are you seen as responsive to their needs? And this is where I think some of the new AI technologies, like the chatbots on websites, can become so much smarter. Because they know — without being creepy — enough about you to say, “Hey Steve, I see that you’re interested in B2B sales. You know, what do you do for the voice of the customer? Because maybe this new research I have might educate you.”
[00:25:00] Ken Rutsky: Yeah, so it’s getting that context and that conversation started — and then always having the option to get a human involved if you’re doing the AI chatbot kind of thing. Being transparent, right? Transparency gets you so much, because if I’m not transparent in the marketing process, why would I be transparent in the selling process?
[00:25:20] Steve MacDonald: You know, like, that’s every bit part of that customer experience, right? Even how difficult or easy was it to go through the contractual portion of the process? Did it take forever? Was it simple? Was it easy? Like, is it just going to be easy to work with you people? We have to make that one of the biggest things that we’re communicating.
[00:25:44] Ken Rutsky: And that goes to your pricing and packaging too, right? One of the things we did here at Aryaka about a year ago is we totally simplified our pricing and packaging.
[00:25:53] Ken Rutsky: We went from literally a thousand-plus SKUs down to dozens, and we made it more predictable and more understandable for the customer. That buying experience — and that ownership experience — just improves dramatically when I can understand what I’m paying, what I’m paying for, and what I can expect to pay in the future.
[00:26:13] Ken Rutsky: So there are so many aspects to this. It’s all-encompassing, and that makes it both challenging and fun.
[00:26:20] Steve MacDonald: You know, I think we have to design like a series where you and I get into this, because there’s so much more I want to cover. But I want to ask the most important question — and that is that, you know, our human brains can remember about two or three things at a time.
[00:26:35] Steve MacDonald: I mean, we’ve covered a lot of territory here, but for your peers — the other CROs, CMOs, CEOs — that are going to be listening to this podcast or watching this podcast, what’s the one thing you want them to take away from our conversation?
[00:26:51] Ken Rutsky: I would say: obsess about the strategic, big problem that you solve for your customers. Get in alignment about why you do that uniquely, how you do that uniquely, and why it matters.
[00:27:02] Ken Rutsky: So really wrap yourself as a team around that big problem — who it matters to, how you solve it, and why it’s better than the other ways to solve it.
[00:27:14] Steve MacDonald: I think that’s brilliant. You know, there was a woman who came on the podcast three times — B2C MO — she’s a value accelerator advisor for Goldman Sachs.
[00:27:23] Steve MacDonald: And she said, “You know, when I’m in front of customers — and by the way, we should be spending 20% of our time talking to customers — here’s my favorite question to ask: What do we do for you?” Right? They feel like, “Well, we work every single day on that problem, right? We know exactly what we do for you.”
[00:27:44] Steve MacDonald: But she said the answers are absolutely extraordinary. And I think it just gets to your point — we’ve got to be ruthless about what it is we’re doing. What is the problem that we’re solving? And the answer isn’t up here in our own heads — it just can’t be. It just can’t be.
[00:28:00] Steve MacDonald: So I’ve loved every minute of this. You know, the whole mission of this podcast is to bring different perspectives and experiences together — from all of us who’ve been in the business for a while, right? Have some battle scars, have some real learning. And if we can share with each other, that’s the rising tide that lifts all boats.
[00:28:25] Steve MacDonald: Ken, you were an amazing part of that rising tide today. I just wanted to say thank you so much. It was great chatting, I enjoyed it, and I look forward to talking again sometime.