Dock to the Future: AI, Freight and Customs with Jack Moberger of DocUnlock

Jack Moberger: Yep, you got it.

Aaron Sheehan: I feel like Jack is a name that used to be more common. Maybe it’s generational?

Jack Moberger: Could be. I don’t see too many younger Jacks these days.

Aaron Sheehan: Yeah, it’s got that old-school feel. Your parents must be classicists – they went with a timeless name.

Jack Moberger: Ha, yeah, something like that.

Aaron Sheehan: That’s actually a well-thought-out strategy.

So, Jack, I wanted to bring you on because you have an interesting background in the B2B space. I’d love for you to introduce yourself – tell everyone who’s listening who you are, why they should care what you think, and also explain why your LinkedIn bio says, Corporate polycrisis is my happy place.

Maybe start with a brief intro, then tell us what the hell that means.

Jack Moberger: Sure. So, my background is a mix of consulting, strategy, and tech – mostly centered around B2B commerce. I’ve worked with a lot of companies that are navigating transformation, whether that’s shifting sales channels, digitizing operations, or figuring out how to handle complexity at scale.

As for corporate polycrisis – it’s kind of a tongue-in-cheek way of saying that I thrive in messy, high-stakes environments. B2B companies often deal with overlapping crises – supply chain disruptions, changing customer expectations, economic shifts. I enjoy helping them make sense of it all and turn challenges into opportunities.

Aaron Sheehan: That always goes over well as a consultant, I imagine.

Jack Moberger: Ha, yeah. It’s definitely a conversation starter.

Aaron Sheehan: The change management piece of that is always the sticky bit. I was actually Googling polycrisis while you were talking, and according to AI – helpful as always – the term was first used in 1999 by a pair of French philosophers. So, technically, it should be pronounced poly-crise. Maybe I’ll have my French general manager fact-check my accent later.

Jack Moberger: Ha, yeah, let me know what he says.

Aaron Sheehan: Perfect segue into Algolia. You mentioned them, and that’s where I first ran into you. I saw you speak at a B2B Online event – I think it was in Chicago or maybe Orlando. They all blend together after a few years.

You were B2B Practice Leader at Algolia, talking about product search and discovery, which makes sense given what Algolia does. For anyone unfamiliar, Algolia is a French-based search and discovery vendor that’s been around for a while. I actually implemented Algolia about 10 years ago when I was an engineer – so it’s definitely got the pedigree.

But what stood out to me was your title – B2B Practice Leader. That’s rare in the search and discovery space. We had Jason Hein on a while back – he had a similar title at Bloomreach, but neither of you are in those roles anymore, and as far as I can tell, those roles weren’t backfilled.

So, I’m really curious – what makes B2B so challenging for search and discovery vendors? Why don’t more companies sustain a dedicated focus on it? And what did B2B Practice Leader actually mean for you at Algolia?

Jack Moberger: Yeah, great question.

B2B is just fundamentally different from B2C when it comes to search and discovery. The complexity is on another level – multiple buyers within a single account, custom pricing, contract-based purchasing, highly technical product catalogs. A lot of search vendors were built with B2C in mind, where search is about maximizing conversions quickly. But in B2B, search is part of a much longer, more intricate buying process.

As for my role at Algolia, B2B Practice Leader meant I was responsible for understanding how B2B companies use search and then shaping Algolia’s offering to fit their needs. That meant working with product teams, advising customers, and generally advocating for B2B use cases.

Aaron Sheehan: That makes sense. But if there’s such a clear need for specialized B2B search, why don’t more vendors stick with it? It seems like companies dip their toes in, then pull back.

Jack Moberger: Because it’s hard.

B2B isn’t just one thing – it’s a mix of industries, business models, and buying behaviors. What works for an industrial distributor isn’t the same as what works for a parts manufacturer or a medical supplier. That means search vendors can’t just sell a one-size-fits-all solution like they do in B2C.

A lot of software companies see the opportunity in B2B but underestimate the investment needed. They assume they can tweak their existing product, slap a B2B-ready label on it, and call it a day. But B2B buyers have different expectations – they need search to handle huge catalogs, map to their workflows, and respect complex pricing structures. That’s not an easy problem to solve.

Aaron Sheehan: Yeah, I completely agree. B2B is broad – there’s no single way to approach it.

From an ecosystem standpoint, a lot of software vendors are realizing the size of the opportunity in B2B. But for many of them, it’s a new challenge. They weren’t built with B2B in mind, so now they’re trying to catch up. That’s why you see a lot of generic messaging – the we support B2B kind of statements that don’t actually mean anything.

At Oro, it’s different. B2B has been our core focus for over a decade. We’ve built our platform specifically for the complexities of B2B transactions – the flexibility, the different ways customers need to buy and sell. It wasn’t a pivot for us; it’s always been the foundation of what we do.

But for vendors coming in from the outside, it’s a steep learning curve. That’s why you see a lot of fluff – because it takes time to actually understand B2B beyond the surface level.

Jack Moberger: Exactly. You need real experience to speak credibly about B2B. It’s one thing to say you support B2B – it’s another to actually build something that works for it.

Aaron Sheehan: That’s an important distinction.

I’ve always had this theory that most of the people who listen to this podcast don’t necessarily think of themselves as B2B vendors. That’s just a business model, not how they define themselves. If you ask them what they do, they’ll say, I manufacture high-end lasers for scientific research – not I’m a B2B company.

For them, the B2B label is almost secondary. The real focus is on the product, the customers, and the value they provide.

Jack Moberger: That’s a great point.

Aaron Sheehan: Totally. Let’s shift gears a bit because you’re no longer at Algolia.

Jack Moberger: That’s right.

Aaron Sheehan: When did you make the switch?

Jack Moberger: I joined my new company in November.

Aaron Sheehan: Got it. So now you’re at DocUnlock. We talked a bit before recording, and I spent some time on the DocUnlock website and your LinkedIn profile.

The world of freight forwarding and brokerage is fascinating to me. I want to read your LinkedIn job description and then have you translate it into plain English.

Here’s what you wrote:

"We sort through, digitize, find typos, and extract cross-check reference numbers from each document just like a person would. We check the totals, make sure the counts add up, and ensure the right units are used to declare weight and quantity. We ensure consistency on HS codes. We drop the end output directly into your ABI, and your CHBs can review and submit with a click."

So, without describing DocUnlock specifically – you’re digitizing a process that isn’t currently digitized. What does that process look like today for the average broker or freight forwarder?

Jack Moberger: Right – so, if you’re a customs broker or freight forwarder, a lot of your job is reviewing stacks of shipping documents and making sure everything is accurate before it gets submitted to U.S. Customs.

Right now, most of that process is manual. Someone has to physically review documents, check for errors, match reference numbers, confirm HS codes, and verify totals. If something doesn’t match up, they have to go back and fix it, which slows everything down.

What we’re doing at DocUnlock is automating that process. Instead of a person reviewing every single document, our system can read, cross-check, and flag errors in real time. It’s like moving from manually doing your taxes to using software that catches mistakes before you file.

Aaron Sheehan: That makes total sense. It reminds me of tax preparation software. My background is in tech, but I started out in insurance and healthcare IT. Those industries have a lot of the same challenges – tons of regulations, lots of paperwork, and a constant need for accuracy.

So, now’s your chance to pitch. How does DocUnlock make this process better? Because as you’re describing it, the industry sounds like it needs a TurboTax for customs brokers. Am I on the right track, or is that the wrong metaphor?

Jack Moberger: No, you’re spot on. Right now, customs compliance is full of tedious, manual work. People spend hours reviewing documents, checking codes, and making sure everything lines up. What we do is streamline that process – reducing errors, saving time, and letting brokers focus on the high-value tasks instead of getting bogged down in paperwork.

Our system digitizes and validates everything before it gets submitted. If there’s a mismatch in the numbers, a missing HS code, or an error in unit conversions, our software flags it immediately. That way, the broker doesn’t have to catch it manually – they just review and submit with confidence.

Aaron Sheehan: Got it. That makes a lot of sense.

If I step back and look at the common thread between your role at DocUnlock and your previous role at Algolia, it seems like you’re tackling the same core problem – taking traditionally offline, labor-intensive processes and making them digital and scalable.

With Algolia, it was product discovery – moving from paper catalogs and sales reps to rich, searchable online experiences. With DocUnlock, it’s taking compliance-heavy manual workflows and turning them into automated, rules-based processes.

So now that you’ve been at DocUnlock for about five months, do you see a common thread in the conversations you’re having with customers now versus the ones you had at Algolia?

Jack Moberger: Yeah, absolutely. The common thread is friction.

At Algolia, the friction was in finding products. In B2B, search isn’t just about showing results – it’s about understanding who’s searching, what they’re allowed to buy, their contract pricing, and how they expect to navigate a massive catalog. The challenge was removing friction from that experience so buyers could find what they needed without jumping through hoops.

At DocUnlock, the friction is in compliance. There’s a lot of manual work that slows things down – reviewing documents, cross-checking codes, catching mistakes before they become costly errors. The goal is the same: reduce friction, improve efficiency, and let people focus on high-value tasks instead of routine busywork.

Aaron Sheehan: That makes a ton of sense. In both cases, you’re solving for speed and accuracy.

So, who’s actually using DocUnlock? At Algolia, your end users were manufacturers and distributors looking to improve search and product discovery. Who’s the primary user in your world now?

Jack Moberger: Our end users are customs brokers and freight forwarders – the people responsible for clearing shipments through customs. They’re the ones who have to process documents, validate details, and ensure compliance before submitting everything to U.S. Customs and Border Protection (CBP).

For them, speed and accuracy are everything. If a shipment is delayed because of paperwork errors, it can lead to fines, extra fees, or major disruptions in the supply chain. We help them get it right the first time.

Aaron Sheehan: That’s interesting. I might push back a little on one thing – and hear me out on this.

We’ve seen companies promise automation before. I’ve been in tech for a long time, and for decades, companies have claimed they could digitize manual processes. What makes this different from the "business process automation" pitches we’ve heard before?

Jack Moberger: That’s a fair question.

The difference now is that AI – particularly large language models (LLMs) – has dramatically changed what’s possible. In the past, automation relied on rigid rules and predefined logic. If a system ran into something unexpected, it would break, and a human had to step in.

What’s changed is that today’s AI can understand documents the way a human would. It’s not just following if-then statements – it can extract meaning, identify patterns, and adapt to edge cases much more effectively. That means brokers can trust the system to handle the bulk of the work, rather than just catching the most obvious errors.

Aaron Sheehan: Yeah, that tracks. The ability to interpret rather than just process is a big leap forward.

It reminds me of how B2B eCommerce has evolved. Years ago, companies thought eCommerce was just another sales channel – that it would replace sales reps. But the ones who truly succeeded were the ones who realized that eCommerce wasn’t a replacement; it was an enhancement. It made sales reps more effective by giving them better data, insights, and tools to do their jobs.

Jack Moberger: Exactly. AI is doing the same thing in automation. It’s not about replacing people – it’s about augmenting their work so they can focus on more valuable tasks.

Aaron Sheehan: That makes sense.

So, let’s zoom out a little. We’re in a moment where B2B companies are rethinking how they sell, how they structure their teams, and how they leverage digital tools. You made a comment to me in an email that really stuck with me. You wrote:

"Sales isn’t going out of business. Look at what software companies went through with free trials and PLG (product-led growth) in the early 2010s. People thought it would replace sales, but now we have more AEs than ever. B2B is going through the same shift. What looks like channel risk is actually the biggest telemetry, transparency, and intent signal they’ve ever seen."

That’s fascinating. Can you unpack that?

Jack Moberger: Yeah, absolutely.

There’s this recurring fear in B2B that digital tools – whether it’s eCommerce, AI, or automation – will replace sales. But history tells a different story. Look at what happened in software. In the early 2010s, we saw a massive push toward PLG (product-led growth) – free trials, self-serve onboarding, usage-based pricing. The idea was that buyers wouldn’t need sales anymore because they could just try the software themselves.

What actually happened? Software companies ended up hiring more AEs than ever before. Why? Because once customers engaged with the product, companies suddenly had better data on who was serious about buying. Instead of cold-calling or chasing down leads who might not be interested, sales teams could focus on the highest-intent buyers.

Aaron Sheehan: Right – they weren’t selling less, they were selling smarter.

Jack Moberger: Exactly. And that’s what’s happening in B2B today.

Some companies still see eCommerce or AI-driven tools as a channel risk – meaning they worry it’ll take business away from sales reps. But in reality, it’s the opposite. These tools generate telemetry – meaning they give you data about what customers are doing, what they’re interested in, and where they are in the buying process. That’s gold for sales teams.

If a customer is looking at certain products, starting a quote, or browsing a knowledge base, that’s a signal. It tells sales exactly where to focus their efforts instead of treating every prospect the same.

Aaron Sheehan: That’s a huge shift in mindset. Instead of thinking, eCommerce is stealing our sales, the smarter companies are thinking, eCommerce is giving us better visibility into our customers.

Jack Moberger: Yep. It’s not about replacing sales – it’s about making sales more data-driven.

Aaron Sheehan: I love that. We see this at OroCommerce all the time. Our platform captures user behavior – what customers are searching for, what quotes they start, what products they add to their cart but don’t buy. That’s valuable information for a sales team. But a lot of companies still aren’t using it to its full potential.

Jack Moberger: Right. Because it requires a cultural shift. Some sales teams are still operating in a world where they believe every sale comes from their direct effort. The idea that digital tools could support their role – rather than compete with it – is a shift.

But if you look at the companies winning in B2B right now, they’re the ones figuring out how to blend digital tools with sales teams instead of treating them like separate things.

Aaron Sheehan: Totally.

Alright – let’s talk predictions. You’ve made some great observations on digitization, AI, and automation. You don’t describe yourself as a futurist, but you’ve definitely made some futurist-adjacent takes.

So, let’s put you on the spot. With all the recent activity around tariffs and global trade, how do you see things shaking out for brokers and freight forwarders over the next year? And how is DocUnlock preparing for it?

Jack Moberger: Yeah, it’s been a wild few weeks in global trade.

Every time a major tariff policy changes or a new trade restriction comes into play, it sends shockwaves through the brokerage and freight forwarding world. And that’s exactly what we’re seeing now. The moment a Wall Street Journal article drops about new tariffs, brokers suddenly become the most in-demand people in the room.

From a DocUnlock perspective, these shifts are actually good for us in the sense that they increase the demand for accuracy and efficiency in customs compliance. More tariffs mean more complexity – more documentation, more classifications, more potential for costly errors. The companies that can process those changes quickly will have a massive advantage.

Aaron Sheehan: Right – because with every new tariff, there’s a flood of new paperwork and potential fines for getting it wrong.

Jack Moberger: Exactly. And a lot of brokers still rely on manual processes to keep up with it all. That’s fine when trade is stable, but the moment things get chaotic, the cracks start to show.

What we’re seeing is a shift toward more automation in customs brokerage – not to replace brokers, but to help them scale. The firms that can process documentation faster and more accurately will win. And that’s where we come in.

Aaron Sheehan: So if I had to summarize, your short-term prediction is high noise, low certainty – meaning a lot of policy changes, a lot of confusion, and a lot of scrambling to adjust. But long-term, we’re looking at a move toward automation and a more structured approach to managing compliance.

Jack Moberger: That’s exactly right.

Aaron Sheehan: Makes total sense. I have a longer economic history rant on the effectiveness of tariffs, but I’ll save that for another podcast.

Alright – final question. This one’s never in the prepared notes, but if you’ve been listening to the podcast, you know what’s coming.

Name a piece of media – a book, a podcast, a show, an article – that you’ve consumed recently and would recommend to our listeners. And no, it doesn’t have to be about customs brokerage.

Jack Moberger: Ha, good. Because I don’t think I could name an exciting customs brokerage book.

I’ve been really into The Three-Body Problem series lately. The books are incredible, and I just started the Netflix adaptation. It’s heavy, but fascinating.

Aaron Sheehan: Solid pick. I’ve read the books, and I’ve started the Netflix series too. It’s definitely one of those need-to-be-in-the-right-mindset kind of shows. Not exactly a light watch.

Jack Moberger: Yeah, you definitely need to be in the right headspace for it.

Aaron Sheehan: We’ll link to the books in the show notes. If you’ve got an Amazon affiliate link, now’s the time to pass it along – I hear this podcast moves product.

Jack, this has been a fantastic conversation. I feel like we could have gone on for hours about some of these topics. Maybe we’ll have you back for a follow-up at some point.

Jack Moberger: I’d love that. This was great.

Aaron Sheehan: Appreciate your time. Enjoy the rest of sunny St. Pete – beautiful time of year to be there.

Jack Moberger: Highly recommend. Thanks so much.