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What Ecommerce Leaders Told Us About the State of Delivery in 2026
ShipStation Global’s Innovation Delivered brought together some of the sharpest minds in ecommerce, logistics, and supply chain around the central idea that AI and automation aren’t just changing how brands ship, they’re changing what delivery means altogether.
Across sessions, speakers and panelists tackled questions ranging from the real ROI of AI and the economics of free shipping to the post-purchase experience and supply chain volatility.
Here is a collection of 38 of the most insightful and actionable quotes from the entire event from the people building and running the operations that define modern ecommerce.
From manual workflows to operational discipline
Across sessions, experts described the hidden cost of manual shipping decisions and framed automation as something that doesn’t replace judgment, but instead frees teams from repetitive work. These perspectives also suggest that automation is more about disciplined processes and clean data than the technology alone.
Most operational problems stay hidden until someone maps the work:
Most retailers with operational problems suffer from an awareness problem. They don’t know their problems because they’ve never written down their process. I would task someone with literally following the parcel from the moment the order is captured until the customer confirms it’s been delivered. By the end of that exercise, you’re usually embarrassed at how many manual steps there are.
Rick Watson — Founder, Watson Weekly
Automation has a way of exposing problems you’ve been ignoring:
Automation can’t solve problems it didn’t create. If you don’t have the right weights and dimensions for your products and boxes, automation will make things worse. It’s going to expose all the inefficiencies your humans were quietly working around.
Aurélien Leftick — Senior Director of Strategic Partnerships, WooCommerce
Disconnected systems create problems that people end up solving by hand:
When your ERP and shipping platform operate in data silos, you’re forcing your warehouse staff to act as human middleware by manually reconciling data and duplicating entries. The danger isn’t just wasted time. It’s data degradation and latency. A single manual typo can cause a misshipment or a broken financial ledger.
Daniel Oh — Vice President of Business Development, Acumatica
The biggest gains often come from automating the ordinary:
Most merchants, even those with varied SKUs, can find similarities or consistencies across about 80% of their shipments. When you automate that process upstream, you eliminate inconsistencies in service level, operations, and transportation.
Matthew Carpentieri — Sr. Manager, Strategic Partnerships, DHL Express
Automation amplifies whatever process already exists:
Automation can save a lot of time and money, but the problem isn’t always a technology problem. Automation can do something at scale, but if your process isn’t well defined and your data isn’t sound, automation can mean more mistakes than you had before.
Rick Watson — Founder, Watson Weekly
Headcount shouldn’t be the default answer to growth:
When people don’t automate their process, they will have to increase headcount. As long as you rely on humans to think and process things without systems, your payroll is going to increase.
Maïré BAVARDAY-ROSA — CEO, ecomspaces
Peak season becomes much less stressful when the work is already automated:
We have not had to hire seasonal staff to handle a 30% to 40% increase in direct-to-consumer volume through the holiday push. And it’s not only been a cost savings, but a lot less stress for our leadership team that doesn’t have to manage additional staff.
Ned Woodward — Director of Logistics & Fulfillment, Spiceology
AI beyond the hype: better decisions, cleaner data
Speakers pushed past the marketing language around AI to talk about the actual value it’s creating today—less as a replacement for people and more as a way to improve decisions, resilience, and operational visibility.
The biggest AI wins are happening behind the scenes:
AI is at its best when it does blue-collar work for white-collar workers. It’s helping with reporting, data analysis, customer service, and product enrichment. It’s improving scalability, helping merchants forecast and fulfill, and taking off their plate the work that frees their people to add more value.
Darin Lynch — Founder & CEO, Irish Titan
AI can’t fix uncertainty in your data:
You can’t have your data held in 10 different locations. You have to get it all together because AI can do incredible things, but it needs access to accurate, unquestioned data. You need confidence in it.
Bill Fraine — Senior Vice President of National Sales, USPS
A shared understanding beats another dashboard:
The goal shouldn’t be more dashboards. It’s about making sure everyone is working with the same version of reality.
Patrick Koehler — Founder & CEO, KD Global USA
Not every AI promise survives contact with reality:
If you’re trying to evaluate a technology and that vendor is including a lot of AI in their messaging, ask to see an actual production customer. Ask how much human intervention is required. If they’re advocating for little to no human-in-the-loop, that’s a yellow flag.
Darin Lynch — Founder & CEO, Irish Titan
AI is changing how customers discover brands, not just how brands operate:
Shoppers can use AI and just tell ChatGPT or Claude what they want, and ask the platforms to find the best one that has it in stock at the best price. I think it’s a huge net positive for smaller retailers with a differentiated product. Now shoppers can find the products without the brands paying the Google tax.
Aaron Rubin — CEO, ShipHero
Shopping is becoming less about search and more about trust:
I think it’s going to change our relationship with shopping. And it’s not just about price or free delivery. It’s about reputation and reliability. AI allows us to bring information on many attributes together really easily to simplify the shopping experience.
Lora Cecere — Founder & CEO, Supply Chain Insights
The real cost of “free” shipping
The sessions tackled one of ecommerce’s most contested questions: has free shipping ruined margins, and who’s responsible for fixing it? The conversation ultimately shifted from debating free shipping to understanding the economics and customer expectations behind it.
Some ecommerce advice has outlived its usefulness:
In 2026, the idea that you need free shipping only as a conversion lever is dated advice.
Rick Watson — Founder, Watson Weekly
Customer experience is bigger than one shipping offer:
Offering free shipping is not the singular thing that’s going to drive conversion or make the difference in a positive customer experience.
Nate Skiver — Founder, LPF Spend Management
The real question isn’t whether shipping is free but how you pay for it:
By my count, there are about 42 different ways to provide free shipping, and they have wildly different costs. I would argue that free shipping is actually built into our subconscious brains. The updated version of Maslow’s Hierarchy of Needs probably has free shipping on it.
Jason Goldberg — Chief Commerce Strategy Officer, Publicis Groupe
The fear of change often costs more than the experiment:
Those that have tested tiered shipping levels have almost uniformly found that conversion held better than they feared. The fear of testing whether you have free shipping or not is worse than the test itself.
Matt Hertz — Founder & CEO, Third Person
You can’t improve what you don’t measure:
I recently did a survey on 70 3PLs looking at cost-to-serve, and I found that only 2% are really analyzing cost-to-serve deeply.
Lora Cecere — Founder & CEO, Supply Chain Insights
Sometimes the highest cost isn’t shipping at all:
The person who ate everyone’s margin is Mark Zuckerberg. Brands spend twice as much on Meta as they do on UPS, FedEx, and USPS combined. If you can figure out Meta, you can definitely afford free shipping.
Aaron Rubin — CEO, ShipHero
Free shipping only works when it supports the business behind it:
I think logistics is part of the brand promise. If you’re operating a commodity business and offer free shipping, you’d better be sure you’ve accounted for the 3PL. But if you have a differentiated brand, logistics is very little of what’s driving that brand promise.
Lora Cecere — Founder & CEO, Supply Chain Insights
Delivery as the brand promise
Delivery is no longer just a back-office function. It’s one of the last touchpoints a brand fully controls, and speakers across multiple sessions argued that visibility and proactive communication are what make a brand’s delivery promise believable.
Customers judge the promise after they click “Buy”:
Anyone can make a great advert or build a beautiful website. The real test is whether it lives up to the promise you’ve made after someone clicks. Brand voice must continue beyond the advert.
Chris Forbes — Co-Founder, Cheeky Panda
The brands that win treat delivery as part of the product:
Delivery is no longer a cost. It’s an experience.
Sham Aziz — Founder, thecxway
Reputation is earned one shipment at a time:
There’s definitely a tipping point. Newer brands focus heavily on their product, but there comes a point when they realize that consistency and reliability are part of building their brand reputation.
Dana Nino — Vice President, UPS
Loyalty is built through dozens of small moments:
Every step of reinforcement—the right notification, the right nudge, the right language, the right tissue paper, the right in-flight options—all of those are casting a vote for loyalty and repeat purchase.
Sham Aziz — Founder, thecxway
Smaller brands can turn service into a competitive advantage:
Our standard shipping may be slower than Amazon’s, but what you get is human customer service. You get surprise-and-delight experiences in your package. We’re turning some of our disadvantages into a competitive advantage. Delivery is a brand experience.”
Brian Bianchetti — CEO, People’s Choice Beef Jerky
Honest communication matters more than perfect delivery:
Certainty and transparency are key. Even if you’re delayed, as long as you communicate it honestly and fix it next time, you’ll get a happy returning customer.
Patrick Koehler — Founder & CEO, KD Global USA
The wrong message at the wrong time can undo a great experience:
Customers want to feel heard. They want to be acknowledged throughout their journey. If you send that upsell email when the customer’s package has been delayed three times and hasn’t arrived yet, that’s not going to land well.
Dan Caldwell — Technology Partnerships, Klaviyo
The best carrier relationships prevent problems before they happen:
Talking to your carrier is the biggest thing. If you’re the one who has to manage it day to day, you’ve got the wrong partners.
Bill Fraine — Senior Vice President of National Sales, USPS
Customer experience breaks down when teams work in silos:
It’s not just about the data. It’s about collaboration. It is way too common for the teams responsible for logistics, marketing, and customer support to not be working closely enough together.
Dan Caldwell — Technology Partnerships, Klaviyo
Trust usually breaks before the shipment does:
Sometimes the first thing that breaks isn’t actually shipping. It’s trust in the data. As brands scale, carriers, warehouses, and sales channels all start looking at different systems and getting different answers.
Patrick Koehler — Founder & CEO, KD Global USA
Modern operations are managing decisions as much as deliveries:
Visibility gets harder as complexity increases because you’re not just tracking packages anymore. You’re tracking decisions.
Bethany DeAngelo — VP of Product, ShipStation Global
Visibility gives brands an advantage long before the package arrives:
Giving full visibility to everyone in the chain gives us an edge over dropshippers, where something dispatches from a warehouse, and two weeks later it just turns up at your doorstep.
Sarah Gulfraz — Ecommerce & Logistics Director, Peacock Fulfilment
The most valuable marketing email isn’t promotional:
The tracking email is the number-one read email in ecommerce. That’s not a secret. So it’s both a logistics touchpoint and a huge marketing opportunity. The teams need to collaborate. Just deciding who owns that touchpoint is a meaningful first step.
Rick Watson — Founder, Watson Weekly
Why scaling shipping gets so complicated
As brands scale across warehouses, carriers, and borders, speakers discussed where operations typically break. Experts also addressed the role of operational readiness and compliance on global growth and how to adapt to constant changes to de minimis rules to avoid bad surprises at the doorstep.
Complexity usually breaks the process before it breaks the technology:
The breaking point isn’t usually when a company adds a second warehouse or when they try to add additional carriers. It’s when they try to scale their business but still operate as a single-location business.
Bethany DeAngelo — VP of Product, ShipStation Global
Flexibility becomes a competitive advantage when markets change:
Having some diversity in your carrier base helps. If you have options and competition within your carrier base, you have potential to move volume to other carriers when your primary carrier raises rates.
Rick Watson — Founder, Watson Weekly
Policy changes can reshape an entire operating model overnight:
De minimis isn’t just a tax rule. It’s an entire operational architecture. Brands have built their entire cross-border model around de minimis.
James Marley — Vice President, Cross-Border, Swap Commerce
Global expansion rewards patience more than speed:
Don’t try to go completely global out of the gate. Pick a lane where you’re seeing a lot of volume, manage those complexities and compliance requirements, and then expand from there.
Mohammed Baloch — General Manager, GlobalPost
A surprise at the doorstep becomes a brand problem:
A duty bill on the doorstep is about as bad as it gets, and it’s going to increase acquisition costs in core markets.
James Marley — Vice President, Cross-Border, Swap Commerce
Taken together, these perspectives from ShipStation Global’s Innovation Delivered point to a clear pattern. This year’s smartest ecommerce brands treat delivery as a core part of their brand promise and ground every decision in clean data and disciplined process.
Whether it’s automating the ordinary, pressure-testing the true cost of “free,” or making a delivery promise they can actually keep, the operators who pull ahead are the ones who stopped guessing and started knowing their own numbers.
Watch all the sessions on demand for more comments and insights on today’s ecommerce landscape from the event.
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