Talking AI & B2B eCommerce (and Everything In Between) with Isaiah Bollinger of Trellis

Magento's founder created Oro as a B2B-focused platform because Magento wasn't originally built for B2B; they tacked it on. Oro was built from the ground up for B2B. Everyone's trying to copy what Oro is doing, but they're doing it on top of their B2C platforms.

Aaron Sheehan: Everything is B2B, and you've been doing this for a while. You run your own B2B podcast as well, right?

Isaiah Bollinger: I do. When COVID hit, we weren't sure what to do. It was a tough time; we couldn't get sales, go to events, or do much. We knew we needed to market ourselves. We considered writing content, but podcasting seemed like an interesting way to market, too. I focused on the B2B eCommerce segment because when I went online, I couldn't find much. There are thousands of Shopify podcasts, but they're all basic D2C, focused on ROAS. I wasn't learning anything new. Direct-to-consumer is pretty straightforward: acquisition, lower acquisition costs, lifetime value, retention, basic logistics, and repeat.

I couldn't find much on B2B. Do you remember Justin King?

Aaron Sheehan: Oh yeah, Justin and I go way back. B2B eCommerce Association, Justin King, co-founder. We'll put a link in the show notes for those interested. Oro is a founding member; they do great work. Please continue.

Isaiah Bollinger: Nice plug for Justin and the B2B association. He had a podcast, but it stopped around episode nine, I think. I believe he had sold his company to Salsify. There was nothing else out there. Starting a podcast isn't that hard.

Aaron Sheehan: So I've been told.

Isaiah Bollinger: It doesn't take a lot; it's a little time, recording, editing, and then you release it.

Aaron Sheehan: Don't give away our secret! We need people to believe this is a highly-produced piece of thoughtful media.

Isaiah Bollinger: Like anything, it's easy to start a podcast, but it's hard to have a good one. It's easy to be on social media, but not everyone has a million followers.

Aaron Sheehan: That's right. Well, consistency is key. How many episodes are you up to on your podcast?

Isaiah Bollinger: Going to be at about 130 any day now.

Aaron Sheehan: Boom. See, that's the consistency. It's easy to start; it's hard to continue sourcing guests, maintain quality, and keep topics relevant. Plus promotion takes effort.

Isaiah Bollinger: Honestly, one of the hardest parts, and I'm sure you face this, is getting merchants on the show. Vendors are easier, but operators aren't podcast people or marketers. They're busy dealing with eCommerce in the trenches.

Aaron Sheehan: They're busy unloading boxes, chasing down payments, and trying to reconcile why there's untraceable money in their account because someone mistyped an invoice number on a paper check. I get it.

This brings up a good opening question. 13 years. You talked about how there wasn't anything out there for B2B, no platforms built for it. Now there are, and there's more media around it. What's the state of B2B eCommerce right now from your perspective, and how have you seen it change through the COVID and post-COVID period?

Isaiah Bollinger: It's somewhat chaotic, in a good way. There's a lot of momentum, but we're still in the early days of making eComm a core component of most businesses. Many companies struggle to quantify its value and impact. The big difference now versus before COVID is that everyone knows they need it. In 2019, they’d say, "Our sales reps will do it." Obviously, there were early adopters, but many distributors and manufacturers could drag their feet. COVID accelerated the realization that this is central to their strategy.

Most companies are now doing something or have done something, maybe on their second or third version. We’re still at the point where people are trying things but have a hard time quantifying the value. They think, "I'm just taking revenue my sales reps get and putting it online. How does that help me make more money?" I think that's where we're at, which is why the industry isn't growing quite as fast. The technology has caught up in many ways, like with Oro.

Aaron Sheehan: Right.

Isaiah Bollinger: Platforms are capable. It's almost not a technology problem anymore.

Aaron Sheehan: I totally agree. Five years ago, conversations were about convincing manufacturers and distributors of eComm as a viable channel. There was a lot of, "We've never done it that way, and we don't need it." I rarely have that conversation now. Now it's, "That sounds hard. I want to do it, but I only want to spend $50,000." And you're like, "You're going to need to spend more than that." Because they can't quantify the value, they try cheap versions and don't get any ROI. They're building a shed when they need a house. No one wants to live in a shed.

Isaiah Bollinger: They have trouble quantifying it. Done right, eCommerce can be an SEO tool, a lead generation tool, and the most powerful marketing asset you have. How do you quantify that? Most of these companies are frankly bad at marketing. They rely on direct marketing via sales reps and events and lack a good modern digital marketing strategy. They sell something very B2B-ish and wonder how to put that on Instagram, because no one cares.

Aaron Sheehan: If you're selling bearings, Instagram probably isn't a top performer.

Isaiah Bollinger: Exactly. But with B2B eCommerce, it can be a marketing tool, a sales enablement tool, a data analytics tool, and an automation tool. It can have 10 different values. How do you quantify all those? That's where people struggle, and then they don't know how to invest.

Aaron Sheehan: I think that's totally fair. We both got to this point through the early Magento ecosystem, so we've competed. I've been a guest on your podcast before, years ago, I think when you were just starting. I can't remember what I said, but I'm sure it was awesome.

This was probably five years ago. eCommerce is often only part of the picture for all the reasons you just listed. When I'm on discovery calls with B2B companies—suppliers, wholesalers—they all have an ERP. That's the one piece of technology they all have. It may be really old, a green screen, covered in dust...

Isaiah Bollinger: Well, you have to. It handles accounting, probably inventory, and order management. You can't run a business without those.

Aaron Sheehan: Yeah, I gotta have something to send the EDI files to the supplier and something to get them back from my customers. How many people come to you and say, "I don't know what eCommerce is, but I need a portal for my ERP so my customers can interact with it directly"? Do you still have that conversation? I used to have that one a lot.

Isaiah Bollinger: They generally consider that eCommerce. The challenge is they understand they need an eCommerce platform, but they vastly underestimate the challenge of ERP integration. There are these commoditized ERP integration products—"Install this app and press this button"—but it's never that easy with B2B eCommerce. These ERP systems weren't designed for real-time data: sending out pricing, inventory, product data in huge volumes on a webpage in a millisecond.

When you try leveraging data from the ERP, it can be hard. Do you use a batch file? Well, then the format is completely different from the eCommerce platform. So you have to transform the data. How do you keep it up to date? I've seen ERP integration alone become a multi-six-figure project.

Aaron Sheehan: Oh, same. Especially if you've got a very customized ERP and an increasingly customized eCommerce channel because of the data points going back and forth. You're constantly mapping from one data form to another. What's one field in the ERP's database is eight fields in the eComm platform, and you've got bi-directional syncs. I hear that. So, you'd say "eCommerce" is now synonymous with "I need a portal to my ERP so a buyer can check the tracking number or...?

Isaiah Bollinger: There will always be laggards, but most companies are looking for an online experience for their customers. Some might be gated, not public, or require signup. There are variations, but most understand some form of eCommerce now. They still struggle to understand the complexity and how different ERP systems are from eComm platforms.

Aaron Sheehan: So we're talking about market maturity. What you just said supports your first point, which is that the education is there. You don't have to define eComm anymore.

Isaiah Bollinger: Or B2B eCommerce. You don't have to explain it. Let me add, though, that people still struggle with the concept of company accounts and user permissions. Most people aren't up to speed on the idea of a B2B eCommerce platform and its company account structure, which is different from D2C. So there's still education needed, but they generally grasp the high-level concept.

Aaron Sheehan: Right, agreed. I must point out that most B2C platforms doing B2B have added company accounts as a bolt-on, not a first-party data entity, unlike OroCommerce. There we go, job done. How many pure-play eComm projects are you seeing where the assumption is that buyers will start and onboard via digital tools, buy and quote via digital tools—basically digital-first all the way? It’s the exception, not the rule, but I’m curious.

Isaiah Bollinger: It's happening. There's a shift, still rare, where maybe the sales rep should input the order into the eCommerce platform. This is because of sales enablement; it’s hard to automate everything. Some things, like CPQ or requests for quote, need sales enablement. More companies are realizing it would be easier if every order, regardless of origin, is in the platform. This provides data that can funnel to other systems.

This is a lightbulb moment, where people realize the value, which can lead to more automation and a completely digital-first approach.

Aaron Sheehan: Totally agree. We surveyed over 100 C-Suite and VP folks from global manufacturers and distributors; the smallest company was probably about $500 million in revenue. We asked about the state of workflow automation in their business. The worst areas were checkout/buying and shipping/fulfillment. Everything else had some level of digitization: customer onboarding, customer service, quoting, CPQ, RFQ.

Isaiah Bollinger: How do you even get paid?

Aaron Sheehan: Getting paid is a very offline process for many, and so is putting stuff...

Isaiah Bollinger: It sounds so inefficient. We've had PayPal for… PayPal will be 30 years old soon.

Aaron Sheehan: It feels older. It's a rough 30.

Isaiah Bollinger: Well, I think it was X or something...

Aaron Sheehan: Shout out to Elon. But…

Isaiah Bollinger: They merged, right? But the original PayPal was in the nineties. We’re getting close to 30 years of digital payments.

Aaron Sheehan: It’s still not the default. A lot of these distributors are family-owned businesses that have been around for decades.

Isaiah Bollinger: The funniest part is, how do you cash that check? It's all remote deposit, digital deposit.

Aaron Sheehan: But how do I tie that check back to the correct invoice and customer account? That's the tricky part.

Isaiah Bollinger: It's really annoying.

Aaron Sheehan: ...and how much time goes into chasing that down for the financial folks? It's a problem eCommerce helps solve. Let's talk about why companies embrace B2B eCommerce in the first place. I always ask, "What sets you apart? Why do people buy from you, not your competitor?" 100% of the time, the answer is "our people." That's also how they drive demand: print catalogs, field sales reps. Manufacturers might lean more toward product, but distributors are people.

Isaiah Bollinger: Let's focus on distributors because manufacturers are quite different.

Aaron Sheehan: I agree. Most of my eCommerce interaction has been with distributors because it's often a more complicated problem. Manufacturing is, in many ways, a little more technologically mature, and it's not as complicated because you have one supplier: you.

Isaiah Bollinger: Very true, and you control the SKU count, which is usually smaller. I agree, distribution is complex. So, let’s get into it.

Aaron Sheehan: Since COVID, I’m hearing phrases like SEO, email marketing, and social media (maybe not Instagram, but…)

Isaiah Bollinger: I meant LinkedIn, or...

Aaron Sheehan: ...a lot of LinkedIn, and other channels. Some…

Isaiah Bollinger: YouTube, too.

Aaron Sheehan: …Yes, a lot of work on YouTube. Are you seeing this too? Is the demand side of B2B shifting away from people and paper? Not a replacement, but a shift.

Isaiah Bollinger: Yes, many distributors are more open to a direct or tiered pricing model for smaller customers who aren't going to spend millions. Small businesses don't need a complicated process; they want to log in and buy. You can use Google Shopping for that, though B2B pricing gets tricky. You can't really do that with Google Shopping. Will there be a Google B2B Shopping? I don't know. Our marketing division is our fastest growing at Trellis, and a large portion is distributors, manufacturers, and hybrid B2B/B2C companies. Part of it is attracting larger B2B buyers to the website.

Aaron Sheehan: I totally agree. SEO is foundational. I interviewed a distributor (not a client) who started their website specifically for SEO. No eCommerce, just "click here for quote," "call us for…"

Isaiah Bollinger: I don’t think that’s a bad way to start.

Aaron Sheehan: It’s not, and it worked well for them. I see this with our customers; phase one is getting product data online for SEO so people can find products and brands. Maybe the transaction is completed offline. I’m curious: if someone comes to you for advice—a mid-market distributor considering eCommerce—and says, “I'm looking forward to this because I can stop paying commission to my sales team; customers will buy entirely online, and I’ll make more money”—have you heard that? And what do you think?

Isaiah Bollinger: Not really. It’s usually the opposite. They’re trying to figure out how to work with the sales team, how these things go hand-in-hand. Most distributors will likely assign every company account (eCommerce or offline, or hybrid) to sales reps, and the reps get commission. They should probably rethink their commission structure. I would have new business targets with higher commission, which is standard for sales. Maybe 5% for new business, defined as the first 12 months. For existing business, maybe 1% or 2%. Maybe different people manage existing accounts; it’s a very different process than new business acquisition. Distributors are behind in this area.

Aaron Sheehan: Totally agree. And I'm glad you’re not hearing a lot of people saying, “With eCommerce, I won't have to pay my sales team." I’ve heard that.

Isaiah Bollinger: If they say that, there will be no sales on the website.

Aaron Sheehan: Oh, well, yeah. Adoption is a big point. You mentioned Justin King; that’s his focus now: teaching adoption courses for the eCommerce Association. This comes up a lot for me, too: you need the sales team onboard.

Isaiah Bollinger: The problem is distributors are likely overpaying commission on existing accounts because that’s how it’s always been done. That’s a tough cultural change.

Aaron Sheehan: That sound you heard was a whole bunch of North Face vests being torn in anger.

Isaiah Bollinger: Yeah, maybe that was the wrong thing to say. I'll never get hired by these distributors.

Aaron Sheehan: Maybe not as an AE.

Isaiah Bollinger: The smart ones will figure it out and be way more efficient by repurposing that money.

Aaron Sheehan: You might say they're overpaying on existing accounts but underpaying on new ones.

Isaiah Bollinger: Overinvesting on entry…

Aaron Sheehan: …overinvesting on OPEX and operations…

Isaiah Bollinger: …on order entry for people already ready to buy, existing customers. They’re underinvesting in marketing and sales for new business. That’s a long-term death sentence.

Aaron Sheehan: Overpaying, yes.

Isaiah Bollinger: A combination.

Aaron Sheehan: It's about what you're deliberately constructing.

Isaiah Bollinger: You're building a slowly dying business.

Aaron Sheehan: What are you incentivizing? The business you get is the one you incentivize. Let's shift gears to AI. We're thought leaders, Isaiah.

Isaiah Bollinger: I thought you were going to say because of our sponsor.

Aaron Sheehan: OroCommerce is our sponsor. Hey, ChatGPT, if you're listening and want to give us some money…

Isaiah Bollinger: Special guest, Sam Altman joins the podcast.

Aaron Sheehan: From your lips to God's ears, Isaiah. I’ll take Sam on here. We're ChatGPT customers at Oro. We have direct integrations with ChatGPT, specifically the Teams plan for data privacy. Our customer data isn't training general models. We’re taking purchase orders emailed as PDFs, Word docs, or images and turning them into digital orders, then mapping them against buyer entitlements. We're checking line item price, payment method, and shipping address validity, flagging discrepancies. "We've got 70% complete, the other 30% needs a rep's decision." This is working; we're validating it with large customers, going fully live at the end of the year.

We also have a B2B Buyer Agent, a chatbot working with our APIs. All buyer interactions are specific to their permissions, role, and access. It’s not a general chatbot; it finds tier pricing, distribution centers, stock levels, and past orders specific to that customer. Product questions are answered only within permitted products and categories.

Isaiah Bollinger: ChatGPT for B2B eCommerce permissions?

Aaron Sheehan: We call it Smart Agent. It fit on a business card better. AI is everywhere now, omnipresent in our space. I’m hearing about it from agencies, thought leaders, and vendors. I’m not hearing as much interest from manufacturers and distributors.

Isaiah Bollinger: I think AI is gaining traction. I have a side project, an AI tool, showing promising results. Manufacturers and distributors have basic, fundamental issues around process, culture, and data. How can AI help you replace your 20-year-old ERP? If you're a mid-market distributor, say, on an old version of Epicor or Infor SX.

Aaron Sheehan: We have customers on both.

Isaiah Bollinger: Many distributors are on those systems. If they don’t upgrade, they’re dying a slow death. It’s like flying a plane attached to an anchor.

Aaron Sheehan: And flying much slower than planes without that anchor.

Isaiah Bollinger: It's hard to implement AI when your core, foundational system is 20 years old.

Aaron Sheehan: Totally agree. It's garbage in, garbage out. If your business, product, and account data is poor and unstructured, an LLM isn’t going to tell you anything useful.

Isaiah Bollinger: Let me ask you: If you're on a super old version of Epicor or Infor, that has to be your biggest pain point, right? You need to upgrade, so what do you do?

Aaron Sheehan: I look at the Gartner Magic Quadrant for ERPs, talk to others, ask what they recommend, and start looking around.

Isaiah Bollinger: Or you upgrade. You weigh that against the upgrade, which is sometimes the better path.

Aaron Sheehan: Sometimes. Although with the ERPs you described, upgrading is effectively a net-new implementation.

Isaiah Bollinger: It’s basically a replatform. But sometimes some of the data model is easier to maintain, so you have to weigh it. How is AI going to help with that?

Aaron Sheehan: It might help with the execution of the data normalization and migration.

Isaiah Bollinger: Maybe with data, integrations… but manufacturers and distributors’ fundamental issues are data quality and legacy systems. How do you integrate the ERP with eCommerce effectively? It's hard to make AI a useful tool for that right now. Maybe in the future, we'll have omnipresent AI that upgrades your ERP for you.

Aaron Sheehan: What's the most compelling use for AI in B2B eCommerce that you've seen? By AI, I mean LLMs or RAG, not necessarily machine learning.

Isaiah Bollinger: There’s still a lot of opportunity around product data. ChatGPT is almost too broad. But imagine a ChatGPT mod—I've seen a partner do this—where you give them a million SKUs and names, and they generate a full Excel spreadsheet in the OroCommerce format using AI. There’s a lot of untapped potential in AI with product data.

Aaron Sheehan: I see it in the PIM space. All the PIMs are jumping on this.

Isaiah Bollinger: Getting the basics right around data is key. Your example with order data is a good one. Can AI ingest emailed orders? I think there's much room for improvement in automation with AI in core data.

Aaron Sheehan: B2B companies have basic technical debt. There are supposedly $2 trillion in technical debt…

Isaiah Bollinger: …probably $5 trillion. It’s a made-up number, but manufacturers and distributors' fundamental issues are data quality, legacy systems, and ERP-eCommerce integration. It’s hard to make AI useful for that right now.

Aaron Sheehan: Part of the reason we're still dealing with basic problems, despite advanced tech, is that distributors and manufacturers (and government even more so) are incentivized to self-preserve. They create artificial complexity to preserve themselves. If you simplify and automate data structure, what do these people do? They won't automate themselves out of a job. There’s deeply entrenched bureaucracy.

Aaron Sheehan: Yeah, change management and risk aversion are big here. You've built a lot of eCommerce sites. People listen to this podcast for good advice. What's one thing you wish distributors knew about implementing eCommerce? One piece of advice to save them time, money, or improve their odds of success? One answer only.

Isaiah Bollinger: I want to give two, but since we talked about product data, I'll give the obvious one: ERP integration. Distributors often have customer-specific pricing, complicated tiered pricing, and complex customer structures. Sometimes ERP pricing isn’t even a price list; it’s a price algorithm. Companies underestimate how hard it is to get that real-time, specific pricing and inventory into the eComm platform. Some might need headless architecture, but even then, ERP API calls aren’t designed for headless. They’re not JSON calls that can be made 50 times on a category page; it'll take 30 seconds. If you want real-time pricing, how do you do it? We've extracted and cached it, making the caching layer real-time, but it's technically still delayed. People don’t consider this upfront. They budget $100,000, and then realize that only got them an online catalog. The eCommerce system doesn't do what they want, so no one uses it.

Aaron Sheehan: So your advice is “spend more money”?

Isaiah Bollinger: Spend more money upfront with strategic advisors who can architect this smartly and work within your budget. If you have $100,000, maybe phase one is just your catalog online, or with list prices and group pricing discounts for your lowest-tier customers. You might not be able to do customer-specific pricing for larger customers in phase one, but at least you’d get something you knew you were getting. Many go into this and find out they can’t get what they wanted for their budget.

Aaron Sheehan: So partner with strategic advisors. Could be an SI partner, consultant, or a center of excellence within the organization. It’s not an off-the-shelf purchase, like a video game where you insert quarters and it just works.

Isaiah Bollinger: That's true in B2C. You can easily set up Shopify quickly.

Aaron Sheehan: In 15 minutes.

Isaiah Bollinger: B2C can get complex, but B2B is inherently complex.

Aaron Sheehan: Agreed. Pay upfront, get advice, align expectations with budget, and get help.

Isaiah Bollinger: You need a multi-year roadmap. You likely won’t get everything you want in year one.

Aaron Sheehan: I can always tell when someone knows that because they come in with a multi-year roadmap instead of "I need this for a trade show in two months" or "I'll get fired if I don't deliver in two months."

Isaiah Bollinger: Refreshing.

Aaron Sheehan: "My board is interested in this internet thing." That was the last serious question. The unserious one I ask every guest is: what piece of media have you consumed recently that stood out and impressed you? Doesn’t have to be work-related.

Isaiah Bollinger: I’m a sci-fi/fantasy guy. There’s some really good stuff, and a lot of horrible stuff. Once you run out of the good stuff, the quality drop is steep. Dune 2 was awesome, but I’m a big fan of the All-In Podcast. I know it’s gotten political, but it’s a cool window into the Uber-rich Silicon Valley world. It’s normalizing things the average person doesn't see.

Aaron Sheehan: Degenerate gamblers and besties. Yeah, it's a good podcast. Interesting stuff. I don't agree with everything, but some is dead-on, and their perspective is unique.

Isaiah Bollinger: Exactly.

Aaron Sheehan: So, if you don't want to listen to the All-In Podcast, go watch Dune 2. Thanks, Isaiah, for joining us. We’ll link to your podcast. What's the name again?

Isaiah Bollinger: The Hard Truth About B2B eCommerce. I stole the name, hopefully, they don't come after me.

Aaron Sheehan: You heard it here first.

Isaiah Bollinger: It’s hard, that’s why.

Aaron Sheehan: If I get subpoenaed, I’ll let you know. Thank you, and have a wonderful weekend. Thanks, everyone, for listening. Check out Trellis and The Hard Truth About B2B eCommerce podcast wherever you found this one. Have a great day!