B2B Is Redesigning Everything. The Customer Still Isn't in the Room

Hey there, and welcome to Uphoff on Media, the audio edition. I'm Tony Uphoff. Each week I write about the collision of agentic AI, B2B media, marketing, and technology from the perspective of someone who's actually run these businesses. This is the podcast version of my Substack publication where I take each post and bring it to you in audio form so you can listen wherever you are, whenever it works for you. If you want to read along, go deeper, or subscribe to the written version, you'll find everything at uphoffonmedia.substack.com. Okay, let's get to work. This episode is titled B2B is Redesigning Everything. The Customer Still Isn't in the Room. B2B has been building inside out for 20 years. Agentic AI is about to make that catastrophically expensive. There is a room I keep walking into. The faces change, the industry changes, the agenda changes, but the missing person is always the same. The customer isn't there. I recently sat with a group of senior procurement executives, smart, experienced operators redesigning their workflows for the agentic AI era. The conversation was serious. These were executives working through real transformation. What processes should be automated, what decisions should remain human, how supplier engagement models need to evolve. But something kept nagging at me. The SaaS platform vendors their organizations depend on, the systems of record for procurement, sourcing, supplier management, kept appearing in the conversation as obstacles, not enablers. The procurement teams were clearly articulating what they needed from these platforms to do, New agentic AI features, workflow modifications, integration changes. And the vendors kept saying no, not with technical explanations, not with roadmap visibility, with the soft, faintly condescending resistance of organizations that don't quite understand what their customers are asking for or why. The vendors weren't blocking transformation out of bad faith. They were blocking it because they don't deeply understand how procurement actually works. That's a different and more troubling problem. You can fix bad faith. You can't easily fix institutional ignorance dressed up as process. Then I offered a reframe that landed hard. Throughout the entire discussion, the workflow redesign, the AI feature debates, the vendor friction, not once had anyone mentioned the people this function actually exists to serve. The internal stakeholders, the suppliers, the customers of procurement. The room didn't push back. They recognized it immediately. These were experienced operators. They knew exactly what outside-in thinking looked like. They just hadn't applied it to their own transformation. The problem had pulled them inward and they'd followed it. That's how it always happens. Not negligence, gravity. The same disease, different organs. I've been having a parallel conversation with B2B marketing, media, and technology leaders about brand trust. Same room, same missing person. The data on this is worth sitting with. Studies consistently show that roughly 90% of executives believe their companies are highly trusted by their customers. Customers, when asked, put that number closer to 30%. A 60-point gap. And that gap isn't a perception problem, a communication problem, or a positioning problem. It is a structural orientation problem. B2B leaders have been building brands, systems, and now AI workflows for themselves, not for the people they serve. I don't think this is a coincidence. I think it's the same failure presenting in 2 different organs. We built a generation of B2B marketers who can optimize customer acquisition cost ratios, but have never sat with a customer and asked what they actually need. Look at the last 20 years of B2B marketing. What stands out? Not branding, not the creation of companies that buyers genuinely trust, advocate for, or miss when they're gone. What stands out is the extraordinary rise of digital marketing, martech, and adtech, the relentless optimization of measurable things, click rates, conversion rates, pipeline velocity, cost per lead. These tools aren't the problem. The problem is what happened when they became the entire discipline, when the metric became the mission, when a generation of B2B marketers learned to optimize data but never learned to understand buyers, when the incentive system rewarded what could be measured and quietly penalized what couldn't, like trust, like brand equity, like the kind of relationship where a customer stays through a bad quarter because they genuinely believe in the company. Brand requires something martech can't deliver: genuine outside-in orientation, knowing your customer as a human being making high-stakes decisions with real accountability. That got hollowed out completely. Faith Popcorn named it. Faith Popcorn published a piece recently that I've been sitting with since I read it. Faith is one of the sharpest brand thinkers I've ever I've ever encountered, and she put a name to something I've been circling. She calls it the Heartbeat Brand. The concept is this: consumers trust brands that measure themselves in life outcomes, not transactions. Brands that show up inside the vulnerable, real moments of a customer's life, not just at the point of purchase. Brands that ask, what does this person actually need, rather than how do we move more product? She writes about Costco launching an IVF program, a warehouse retailer deciding that helping its members have babies is also its business. About the USPS carrier who already stops at every door in America and could become a genuine safety net if someone had the vision to see it. About the 60-point gap between executive confidence and brand trust and what customers actually report, and how that gap is not a perception problem, but a strategic blind spot of historic proportions. Her audience is primarily B2C, but the principle lands harder in B2B, where the stakes are higher, the buying decision's more consequential, and the customer has been more systematically ignored. A B2B heartbeat brand is the vendor that shows up in your worst quarter, not just your best. The platform that redesigns its workflow around how you actually operate, not how the product team imagined it. That's the standard. And by that standard, B2B as an industry has been failing for a long time. The SaaS problem is the brand problem. Back to the procurement room. The platform vendors gatekeeping transformation they don't understand are exhibiting the same failure mode as the B2B marketers who built 20 years of campaigns without deeply knowing their buyers. They sold into procurement. they deployed into procurement, they never really learned procurement. That's not a product problem, it's a customer orientation problem, and it shows up as friction precisely when it's most costly, at the moment a customer is trying to evolve, trying to adopt new technology, trying to do the hard work of organizational transformation. If these vendors had developed genuine operational-level understanding of how procurement functions, Conversation would be very different. How sourcing decisions get made, how supplier relationships are managed, how internal stakeholders experience the process, how the job of a procurement leader has changed as the function has become more strategic. The features would exist. The roadmap would reflect what customers need. The no would come with a real reason or not at all. Instead, the customer is in the room and the vendor isn't listening. The mirror image of the procurement team that designs its future workflow without the supplier or stakeholder in the room. It's inside out all the way down. This has always been a risk in the enterprise SaaS market, but the penalty has historically been manageable. Churn is painful, switching costs are real, and inertia protects incumbents longer than it should. Agentic AI changes that calculus entirely. When AI-native tools can replicate and integrate the workflow steps that previously required dedicated point solutions, the switching cost equation inverts. The moat that protected functionally narrow SaaS vendors, quote unquote, we own this step, becomes a vulnerability. Vendors who don't understand the function deeply enough to evolve with it won't just face difficult renewal conversations. They'll be architecturally bypassed. Churn in the agentic AI era won't look like churn always has— a lost renewal, a migration project, a transition cost borne by both sides. It will look like a procurement team that rebuilt its workflow around an AI-native platform and quietly stopped needing 4 of the tools it was paying for. No dramatic exit, no contentious offboarding, just a function that evolved and a vendor that didn't. The vendors who are gatekeeping today are revealing something important. They are not positioned to guide their customers through the agentic AI transition, and their customers are starting to notice. Agentic AI doesn't fix this, it amplifies it. Here is where urgency enters the conversation. Agentic AI is restructuring workflows at the infrastructure level right now. Organizations across B2B are redesigning the interest-to-invoice journey. They are making decisions about what gets automated, what stays human, how suppliers are engaged, how buyers are supported, how the entire operating system of B2B commerce gets rebuilt for a world where AI agents execute tasks, not just assist with them. These decisions will be very hard to reverse. You can pull a bad ad campaign. You can reposition a band— brand. You can't easily re-architect a workflow. That's been embedded into your systems of record, your supplier relationships, and your organizational muscle memory. If the customer isn't in the room during that redesign, we don't just build bad workflows, not when B2B marketers build agentic demand generation without deeply understanding the buyer journey, not when procurement leaders design agentic workflows without engaging the suppliers and stakeholders those workflows serve, not when SaaS vendors build agentic features without operational-level understanding of how their customers actually work. We automate the inside-out orientation. We encode the blind spot at scale. The companies that will compound trust in the agentic AI era are the ones that design outside-in, starting with the customer. The rest will just fail faster. 3 questions worth sitting with. Faith Popcorn ends her piece with a set of questions she recommends sitting with over a good bourbon. I'll offer a B2B version. If your platform, product, or service disappeared tomorrow, would your customers miss it or just migrate? Not the switching costs, the actual loss. There's a difference between a product customers are locked into and one they genuinely value. Most B2B leaders don't know which one they have. When did someone in your organization last spend real time inside a customer's workflow? Not a sales call, not a QBR, but operational time. The SaaS vendors blocking procurement transformation aren't doing it maliciously. They simply haven't spent enough time understanding how procurement actually operates. That's a choice, even if it doesn't feel like one. Who is designing your agentic AI workflows and who isn't in the room? This is the most urgent question in B2B right now. The workflows being designed today will shape how buyers experience your brand, how suppliers experience your procurement function, and how customers experience everything in between for the next decade. If the customer isn't in the design process, you're not building the future, you're automating the past. The gap between what B2B companies think their customers feel about them and what customers actually feel has never been wider. The technology to close that gap has never been more powerful. Neither has the technology to permanently encode it. The question for every B2B leader isn't whether agentic AI changes your business. It does. The question is whether you'll finally put the customer in the room or whether you'll do what B2B has done for 20 years and just do it faster. Put the customer in the room. Well, that's it for this episode of Uphoff on Media. If this was useful, you can find the show on Apple and Spotify podcasts. And if you're so inclined, please subscribe and hit the like button as it helps more people find it. Back at it next week.