Not Just Sales: The True Value of eCommerce for B2B Brands with Jason Greenwood

These days, I look at everything I do through the lens of giving back. How can I give back the best, the deepest, the hardest, the fastest? Whether it’s supporting the B2B eCommerce Association in every way I can, emceeing their events, running my own B2B eCommerce consultancy, or hosting my own podcast—our Wednesday episodes are 100% focused on B2B—everything I do is about sending the ladder back down and helping the industry improve.

I was born and raised in Southern California, lived in New Zealand for almost 30 years where I built my career, and for the last two and a half years I’ve been living in Puebla City, Mexico, with my wife and our two dogs. One we brought from New Zealand, a rescue, and we recently adopted another street dog here in Mexico. No kids—our dogs are our children.

I love this industry. I travel the world, speak at conferences, and try to help as many businesses as I can in B2B commerce. I publish content almost every day in one format or another, on one channel or another. Honestly, I still get up as excited today as I did 25 years ago when I joined this industry. My days are wall-to-wall meetings—I can’t imagine doing anything else.

Aaron: That’s amazing. What a great answer. That enthusiasm—being a friend to the B2B commerce industry—might have to be the show title. We’ll see what other good lines we get, but that’s a great place to start.

Aaron: When I was thinking about topics for this episode, honestly, we could talk about anything related to B2B eCommerce. But there’s something you’ve written about before that I’ve seen throughout my own decade in this space—especially in manufacturing and distribution. I’m just back from several trade shows, speaking to customers, and what strikes me is how often the companies we’re trying to serve are using some kind of homegrown technology for what they call eCommerce.

But even defining what eCommerce means in a B2B context is a wide-ranging question. It can cover everything from product discovery and RFQ/CPQ to web catalogs, punchout, direct web orders, portals, EDI—there’s a long list. But the point is, a lot of the solutions out there are things these companies built themselves, often layered on top of an old ERP, an IBM mainframe, or some green screen system. Sometimes it’s a more modern ERP that just doesn’t do what they need, so they start cobbling things together—using APIs, SQL stored procedures, asp.net, Silverlight, or whatever was available 20 years ago.

How often do you see custom systems in place when you start conversations with companies looking to level up their B2B tech stack?

Jason: For me, it’s not that common anymore—probably less than 25% of the time I see truly bespoke, homegrown commerce tech built on top of an ERP. Usually, their ERP is still a green screen, text-based system, but not necessarily a custom eCommerce solution layered on top.

That said, it does happen, especially in situations like private equity rollups. I worked with one recently in the industrial supplies sector—a distributor and manufacturer with 60 global business units. The PE firm acquired and combined them, so they now run over 40 ERPs globally. In some regions, they have these custom commerce apps built on top of their ERPs; in others, there’s no eCommerce at all—maybe just EDI. And in some cases, they’ve tried to bolt on off-the-shelf tech, usually B2C-focused, and kludged it together with the ERP, but it’s not really fit for purpose.

Outside those rollup scenarios, I don’t see a ton of homegrown stuff anymore. What I do see a lot of is what Oliver Rhodes calls the “dark stack”—shadow IT. In B2B, there are a lot of legacy systems that don’t have meaningful APIs, so you see CSVs dumped to SFTP servers, Google Sheets acting as a pseudo-PIM, data moving around via ODBC connectors. There’s a lot of “spit and baling wire” holding these systems together, especially when companies don’t have a Head of Digital or Head of eCommerce—usually just a Head of IT or Director of Business Systems who’s responsible for making everything work, old and new.

I recently pitched to an industrial supplies distributor in ANZ whose ERP is 20 years old and hasn’t been updated in a decade. It’s a local, almost bespoke ERP, and they’re the vendor’s biggest customer. But there’s hardly any ongoing development. They’re facing a decision: do they try to make eCommerce work on top of this old legacy system, or do they replatform their ERP first? There’s so much custom code, integration is a nightmare.

These are the most common challenges I see: do we start with commerce, or do we first have to fix the back-office system that’s not ready for modern commerce?

Aaron: Totally. We probably see it a bit more in my work, maybe just because of the stage people are at when they engage with us. But it’s why I described eCommerce so broadly earlier, because “shadow IT” covers a lot of these setups—but they’re not doing eCommerce in a way you and I would recognize as customer self-service. Sometimes, there’s not even a portal—just a lot of FTP spreadsheets getting processed so someone can generate a quote and manually type it into the ERP, then email or call the buyer with the price.

I’m curious: what do you think are the internal politics or organizational decisions in companies that don’t have a Chief Digital Officer—which is pretty common? What drives them to end up with shadow IT and this kind of patchwork setup?

Jason: In my experience, especially with distributors, more than 80% of my clients are family-owned businesses—often second or third generation, sometimes even 100 years old. They’ve done things the same way for decades, relying on personal relationships and industry connections. Field reps grew up alongside buyers, went to the same events, played in the same sports leagues, and built their customer base through those personal ties.

But things are changing. Their buyer demographic is getting younger. Traditional buyers are aging out, being replaced by digital natives. Even on the sales side, many of the field experts with all that tribal knowledge are retiring or leaving. The next generation—on both the buy and sell side—expects modern tools. Salespeople don’t want to spend 60% of their time on manual admin tasks when they’re incentivized on sales and commissions. And buyers, who are increasingly digital natives, expect digital self-service. They want to check inventory, see pricing, search catalogs, request quotes, lodge RMAs, download old invoices, check credit status, know who their account manager is, and even send a live chat—all without having to pick up the phone or send an email.

A couple of years ago, I coined the term “Digital Services Layer”—DSL—for all the non-transactional digital services B2Bs should be providing. It’s not just about transactions; customers want to self-serve a lot of things beyond buying.

This is where expectations collide with reality. These entrenched, relationship-driven businesses know they need to adapt, but they have no idea where to start—team, org design, process, tech stack? They know it’s a never-ending journey, not a one-and-done project, but they just need direction on where to plant that first flag.

Aaron: That’s a really good point, and I agree. I’m working with a company right now in exactly that spot—lots of silos, black boxes, old-school ways of doing things. The CEO is on board with modernizing, so IT gets handed the project: “Go figure it out.” The head of IT is confident about evaluating systems, risk, compliance, even negotiating contracts, but he admits, “We don’t know what our customers want, or what sales needs, or how to structure this to drive adoption.” IT can buy things, but they’re not always the best at connecting sales, fulfillment, and customer service to make it work.

When does the pain from all this homegrown shadow IT usually bubble up? Is it security, or more about adoption?

Jason: In my experience, it’s almost always pressure from the customer. They tell the manufacturer or distributor, “This doesn’t work for us anymore.” If a customer is running at 3% margins, and old procurement methods cost them extra, that’s material. If another supplier offers more automated options—say, direct EDI or eProcurement integration—they’ll switch, or at least demand a discount to cover the added cost of doing business the old way.

That kind of pain usually gets escalated to management by the sales team. A big customer complains that doing business is too manual—maybe they still have to fax or jump through hoops to get a quote. When I get involved, my first question is always: how much customer research and feedback have you done before calling me? Have you spoken to your customers, and have you segmented them?

I encourage clients to break their customer base into three buckets:

1. Customers who would adopt self-service eCommerce immediately,
2. Those on the fence who’d need something special to change their habits,
3. And those who simply never will, no matter what you do.

Interview each cohort separately. The last thing anyone wants is to build something that doesn’t fit and won’t get adopted. And beyond that, you want solutions with the flexibility to include adoption by default—like the AI sales agent from Oro, or similar tools, so that even if customers still transact via email, WhatsApp, or whatever, you’re capturing that digital interaction.

I recently saw a customer who said, “Our buyers create purchase orders in a CSV, but don’t know how to attach it to an email. So they take a screenshot and send that image as their order.” It’s not about being tech-savvy or not; it’s just how things get done. Shadow IT isn’t just on the seller side—it happens with buyers, too.

Aaron: That’s such a good point—shadow IT on the buy side. Sometimes it’s a non-company device, and you’re texting screenshots of proprietary info to the seller, who is then expected to fulfill the order. It’s not exactly secure.

And yes, that’s why we built our PDF purchase order-to-digital order AI-powered SmartOrder at Oro—it works with screenshots, pictures, or PDFs, as long as the SKU and info are visible. AI has become such a powerful tool for corralling all these “rabbits”—all the ways buyers and sellers work outside official systems—and bringing them into something IT can actually manage. It’s transformative because we’re not forcing people to change their behavior, but still getting the digital ROI and improvement.

Jason: Absolutely. And what’s made all of this possible is the recent leap in multimodal AI. Now, you can upload a PDF, a CSV, pretty much any format to ChatGPT, for example, and it can process it for you—summarize a 100-page document in two paragraphs, explain the key data in a 10-page CSV, all in seconds. We’ve always had old-school OCR tools, but they were inaccurate and usually needed human input somewhere in the process. With today’s multimodal AI, if the data isn’t totally messed up, it can parse a PDF almost as well as a human would. That’s only really become accessible in the last 6–12 months.

Aaron: Exactly right, and it’s a great observation—and a great segue for us to plug the product!
So, you mentioned earlier that you always ask upfront, “Who have you talked to before you called me?” I’ve been on the receiving end of those calls, and it’s shocking how often the answer is, “No one,” or, “Just our own leadership.” Maybe someone got assigned the project in a Monday meeting and started Googling.

Segmenting your customers the way you described is absolutely the right approach. There are also good ways to segment around margin and revenue growth—like, who always buys the same ten SKUs, who’s more flexible, who’s high-value. One thing I hear a lot is, “The portal or eCommerce is just for our long-tail customers.” Meaning, it’s the cheap and cheerful way to serve the accounts they can’t afford to assign an account executive to. So eCommerce becomes a catch-all for the small accounts—the “5% of our revenue spread across hundreds of accounts.” But don’t worry, they’ll say, Bob (the account manager) will always take care of our strategic accounts. How do you handle that conversation? Do you agree that technology is just for the marginal customer, or do you see it as a key retention and growth tool for your biggest customers too?

Jason: I get that question all the time, and there are always two main points I make.

First, doesn’t Bob or Jane—the account manager—want better tools than just the ERP in front of them? Almost no sales org wants their reps logging into the ERP. They do it today because there’s no alternative, but it’s not what anyone wants. Most reps would rather have a true commerce system: something built for searching products, checking customer pricing, managing quotes, tracking performance. They just want a fit-for-purpose system that lets them do their jobs more effectively.

So, this isn’t just about customers—it’s also about giving your teams the right tools to serve customers at a high level, without hunting through network drives or sending giant zipped folders of spreadsheets via email. Checking specs, filtering product categories—most ERPs can’t do any of this well.

Second, even your largest customers—those transacting via EDI or punchout or eProcurement—still expect to self-serve a lot of things. I was recently running customer interviews for a company launching eCommerce for the first time. We asked their customers if eCommerce mattered to them, and most said, “I love dealing with my account manager. I can call him anytime, message him on WhatsApp, get great service.”

But then I’d dig deeper: what do you love about working with this supplier? What’s painful?
They’d say, “I get long credit cycles, custom products, great account management. But I never know when a shipment will hit our warehouse. We need to schedule our team to receive it, but we get no updates—no shipping notice, no delivery target.”

If they could log in and track an order from dispatch to delivery, they could schedule their team, reduce delays, and turn stock faster. That’s hugely valuable, even if they never use a “buy now” button or see themselves as eCommerce users. For me, eCommerce includes the entire digital services layer—not just transactions.

Aaron: I’m so glad you brought that up. This idea—that eCommerce is more than just a “buy now” button—has become a big part of my own messaging, especially in the last six months. We see so many platforms chasing B2B, but their approach is still very B2C—assuming that the big missing piece is just a faster checkout. But in B2B, a lot of the friction in the buying process is intentional and necessary.

We actually ran a buyer survey recently—about a hundred senior buyers in manufacturing and distribution, mostly mid-market and enterprise. One question we asked was, if you’re not satisfied with your supplier’s buying experience, what should they improve?
When you look at the responses, no one says, “I want eCommerce.” What they ask for is better product information, transparent and reliable pricing, product videos and guides, more details about product fit and attributes, inventory visibility, order tracking—all things that enable them to do their jobs better. Communication and support channels were huge too. They want to move fluidly between online and offline: research some things on their own, get help from a rep when needed, and not waste time going back and forth with clunky processes.

If you can bring Bob (the account manager) together with the buyer—contextually, online—so the buyer can ask questions while looking at their quote, dashboard, or a product page, then Bob can spend less time on repetitive tasks and more time upselling, recruiting new customers, or following up on leads. It’s about using digital to broker those high-value interactions, not just automate everything away.

Before we pivot, do you have a real-world example of this in action?

Jason: Actually, yes—and it’s from a project we’re both involved with right now. The company had a routine customer complaint: on most orders—average of 30 lines per order—at least one item would be out of stock. The real problem wasn’t just splitting orders or managing backorders, but what happens when that out-of-stock item finally arrives.

They found that if the item came back into stock within 30 days, 99% of the time the customer still wanted it. But after 30 days, 90% of the time the customer had sourced it elsewhere and didn’t need it anymore. The old process just shipped backorders as soon as items were available—without checking if the customer still needed them. This led to tons of unwanted returns and lost revenue.

So, in the new system we’re building, when a backordered item comes back into stock, it triggers a workflow:

• If it’s under 30 days, we just ship it.
• If it’s over 30 days, the system automatically emails the customer and asks them to confirm if they still want the item. They click a button to confirm, and only then does it get processed for shipment.

This solves a pain point for both the customer and the supplier. The supplier avoids unnecessary returns and lost margin, and the customer only gets what they actually want—no more surprises or extra admin. That’s the kind of process automation that sits at the intersection of eCommerce and operations, and it’s the sort of thing you just can’t scale manually.

Aaron: I love that example. When I was first interviewing at Oro and saw the workflow engine, it blew me away. It’s not a flashy feature—it’s not headless, composable, or AI—but it powers the kind of automation that brings together people, digital tools, and process to achieve a business outcome. You simply can’t scale if everything requires manual intervention.

Aaron: I want to switch gears since we’re a bit short on time. You mentioned earlier that you’re working with one of our customers and one of our agency partners. What’s your go-to tool for documenting the kinds of requirements you just described? For example, how do you capture and write down a workflow like the one you just shared? And how do you recommend manufacturers and distributors think about documenting internal user stories?

Jason: Good question. I’m actually pretty simplistic in how I run discovery, but I think where I excel is in the quality of my questions. I use a Google Form—a really detailed one, with about 150 to 200 questions. Some are multiple choice, but many are open-ended: “Describe this process,” “How do you go from product receipt to getting it into your ERP and inventory?” I get granular. One major section is the sales cycle—what channels do you sell through, how do you communicate, what internal tools do you use to get info to the customer? I want every step described.

I’m a firm believer that if you ask better questions, you get better answers. One way I demonstrate experience is by asking questions that someone new to the industry might not even think to ask, simply because they’ve never encountered certain scenarios before. That’s where 25 years of experience comes in.

After the customer completes the questionnaire, I follow up with workshops to walk through their answers—clarify anything they couldn’t answer, offer guidance, and dig deeper with follow-ups. I’ll offer examples, share two or three ways I’ve seen something done before, and ask what fits their business. Sometimes they have an entirely new approach I’ve never seen.

Those “on the fly” consulting moments—sharing past experiences, explaining what worked and what didn’t—are where discovery starts to add real value. I’ve even had CEOs tell me that my discovery process was the best they’d experienced in any IT project, and that they learned more about their business than ever before.

Aaron: I totally relate to that. Sometimes, as the architect, your job is less about running the meeting and more about brokering an internal discussion. You might only say three things in a two-hour workshop, but you watch customer service, sales, IT, and operations start bouncing ideas off each other. Someone from the C-suite will be sitting there, wide-eyed, because they’ve never heard all these details discussed together. Once you get people talking, you end up uncovering a lot more projects that need attention.

Jason: That’s so true. I was consulting with a mid-market distributor—about a $300 million, family-owned business. The son of the founders is now CEO and was present in every discovery workshop. Several times during those sessions, he’d turn to someone and say, “Is that really how we do that? When did that change?” He genuinely didn’t know some of the day-to-day processes. There’s often a big gap between the “as intended” process and the “as implemented” process, where teams have developed workarounds just to get things done. If the CEO hasn’t spoken directly to a department head in six months, it’s easy to lose track of what actually happens on the ground.

Have you seen that classic tire swing cartoon? I’ll link it in the show notes—it shows how the customer explained it, how the analyst designed it, how the developer built it, and finally, what the customer actually needed. Each panel looks totally different. It’s a game of telephone, and what the customer really needed isn’t always clear to anyone along the way.

Aaron: Yes, exactly! And let’s not even get into billing—that’s a whole other conversation.

All right, Jason, we’re about done. I’ll close with the question I ask every guest: What’s one piece of media—a book, TV show, movie, podcast, article, whatever—you’ve engaged with recently that stood out and you’d recommend to others? It doesn’t have to be serious, but you can give a serious and a non-serious one if you want.

Jason: I’ll take a different route here. There’s actually a movie I want to see later this year. I saw the trailer last night while scrolling Instagram—it just popped up. It stars Colin Farrell and Margot Robbie, and looks like a big, bold, beautiful journey. Apparently, it’s a romantic fantasy where two strangers meet at a wedding and go on a surreal journey prompted by a mysterious GPS, exploring pivotal moments from their past and contemplating their futures. The cast also includes Kevin Kline and Phoebe Waller-Bridge. What’s interesting is it’s not just about their current lives—it explores their past lives and how they’ve interacted before.

It really grabbed me. I used to go to the movies every week before COVID, but now maybe once every two or three months. I haven’t seen many great movies lately—Top Gun: Maverick was a standout. But I’m genuinely looking forward to this one.

Aaron: That’s a great pick! I haven’t heard of it, but it’s giving me “Before Sunrise” vibes—those bright, reflective, romantic movies. Maybe this is a fresh take on that genre. “Romanticy”—we’ll make that a word!

Thank you so much for joining us, Jason. You shared fantastic advice and lessons for our audience. I’m sure we’ll see each other again soon—maybe at B2B eCommerce World in Scottsdale, Arizona.

Jason: Absolutely, I’ll be there with the rest of the B2B eCommerce Association and fellow ambassadors. Looking forward to it!

Aaron: Can’t wait. Thanks again, Jason.