Thrift e-commerce has always had one unique challenge: Every item is different.
Unlike traditional retail, Goodwill teams don’t work from clean catalogs, repeatable SKUs, or predictable inventory. Every donated item needs to be identified, researched, photographed, described, priced, routed, and listed correctly.
That work takes time and expertise.
During Upright Labs’ recent webinar, “Scaling Thrift E-commerce Through AI-Driven Automation”, four Goodwill leaders shared how pearldive is helping their teams bring that expertise into more parts of the operation — from the retail backroom to the e-commerce listing station.
Our featured guest panelists for the webinar included four secondhand leaders who have been leveraging thrift-specific AI and seeing incredible results for their Goodwill organizations:
Matthew Dillon
Senior E-commerce Manager, Goodwill Easterseals Miami Valley
Sam Jones
Director of Retail, Goodwill Easterseals Miami Valley
Sarah Challender
Director of Digital Sales, Goodwill Houston
Phil Romano
Director of Information Technology, Goodwill Industries of Greater Cleveland and East Central Ohio
Their message was consistent: thrift-specific AI is already changing how Goodwill teams work.
Thrift E-commerce Is Full of Hidden Value, But Manual Work Slows It Down
Most thrift organizations know there’s more value in their donation stream than they’re able to capture. The barriers are familiar: manual listing creates bottlenecks, training is hard to scale, product knowledge varies from employee to employee, and high-value items can be missed entirely.
Sarah Challender saw all of it at Goodwill Houston:
“We had a very large backlog of product, and our listing process was backing up. There was a huge bottleneck. It was very inconsistent.”
— Sarah Challender, Director of Digital Sales, Goodwill Houston
The workflow wasn’t the only strain:
“Training was also an issue, getting people to help identify and create the right titles and descriptions.”
That’s the before-state many Goodwill e-commerce programs will recognize. pearldive wasn’t adopted because AI sounded interesting — it was adopted because there was a real operational need.
pearldive Fits Into the Workflow Without a Heavy Lift
For most leaders evaluating new technology, the first question isn’t about features. It’s about adoption: How much IT support will this need? How long will training take? How much will my team’s day have to change?
Sarah’s answer, after rolling out pearldive at Goodwill Houston:
“It was absolutely seamless. There was no big IT need. My team was trained literally within about 30 minutes, and they were off to the races.”
Matthew Dillon had the same experience at Goodwill Easterseals Miami Valley:
“It almost seemed like there wasn’t an onboarding process. It was completely seamless integration into what we were already doing.”
— Matthew Dillon, Senior E-commerce Manager, Goodwill Easterseals Miami Valley
pearldive doesn’t ask thrift teams to rebuild their workflow. It enhances the workflow they already have, turning photos into researched, optimized listings. Goodwill Houston even moved its e-commerce operation from 14,000 to 42,000 square feet without stopping production.
From Manual Listing to Doubled Production
Before pearldive, Matthew’s team split their day in two: photograph items, then sit down and manually create each listing — the research, the titles, the descriptions, the categories.
“By adopting pearldive, it eliminated the need to sit down and create listings. So production essentially doubled immediately.”
The change also made day-to-day staffing less fragile:
“The consequence of someone calling off is so much less now because of the increased production we’re already getting.”
This isn’t AI replacing employees. It’s AI changing what employees spend their time on. Instead of hours of researching, writing, and categorizing, teams focus on moving more items through the workflow — an operational multiplier, not a headcount cut.
Empowering Teams Instead of Replacing Them
Phil Romano sees the same shift at Goodwill Industries of Greater Cleveland and East Central Ohio, where pearldive has changed how the team thinks about roles and growth:
“It’s given us some flexibility in terms of starting people at that photography stage. And then as they gain experience, they can move to other areas of the business.”
— Phil Romano, Director of Information Technology, Goodwill Industries of Greater Cleveland and East Central Ohio
In practice, that flexibility looks like:
- New team members starting with photography
- Experienced staff moving into quality control
- Subject-matter experts focusing on higher-value review and selection
- Easier cross-training across the operation
- E-commerce knowledge that’s no longer trapped inside a few specialized employees
For mission-driven organizations, that matters. Goodwill teams aren’t just trying to sell more — they’re creating meaningful work, training, and growth opportunities for people. pearldive supports that by making more parts of e-commerce accessible to more people.
Better Listings Help Shoppers See the Real Value of Donated Goods
Listing quality is where thrift e-commerce is won or lost — and it’s exactly where guesswork hurts most. Sam Jones put it plainly:
“Even when you have experts who have been in e-com forever, you don’t know everything. The quality of the listings is just so important.”
— Sam Jones, Director of Retail, Goodwill Easterseals Miami Valley
“If you can take accurate photos, this will tell you exactly what the item is.”
Better titles, descriptions, item details, and condition notes help customers understand exactly what they’re bidding on or buying.
And thrift inventory is unpredictable. One day it’s a saxophone. The next it’s designer apparel. Then it’s artwork, video games, jewelry, collectibles, or vintage electronics. Generic listing workflows weren’t built for that level of variety.
pearldive was.
From $9.99 to $7,000
A Goodwill store manager spotted a saxophone on the sales floor with a $9.99 tag. After running it through pearldive, the team learned it was a 1959 saxophone. It sold online for $7,000.

As Sam told attendees: “A store manager found a saxophone on the sales floor with a $9.99 tag on it. pearldive figured out that it was a 1959 saxophone, and we sold it for $7,000.”
The value is often already in the donation stream. The challenge is identifying it before it’s missed, underpriced, or routed to the wrong channel.
More Production, More Sales, More Mission Revenue
For the organizations represented on the panel, pearldive wasn’t just a workflow improvement. It created measurable business impact.
At Goodwill Houston, the change showed up fast:
“Within one month, our top-line sales increased by 46% within 30 days. It was astronomical.”
In Cleveland and East Central Ohio:
“I’ve seen about a 2x increase in both listing and sales.”

And at Goodwill Easterseals Miami Valley:
“Our revenues are now about 32% higher. While we have incurred more costs, the revenue has outpaced any of it.”
Every operation is different, and no two organizations will see identical results — these are the real experiences these leaders shared during the webinar. But for mission-driven retailers, the implication is bigger than the numbers: more e-commerce revenue means more funding for programs, services, jobs, and community support.
Donation Sorter Brings AI Earlier Into the Thrift Workflow
Auto-Lister changes the listing station. pearldive’s Ama Donation Sorter brings AI into the backroom, where many e-commerce decisions actually begin.
“You snap a couple of photos of an item, and it tells you right away if it needs to go to e-commerce or sell in store.”
Goodwill Easterseals Miami Valley has deployed Donation Sorter across all 44 of its store locations, with a 45th store coming soon. The rollout is also cleaning up the paper trail:
“We’ve done away with paper manifesting. Everything is digital now.”
That connection between retail and e-commerce is the point. It’s not just about faster listings at the warehouse — it’s about helping store teams send better items into e-commerce in the first place.
Sea-Glass Shows Where the Workflow Is Going Next
Sam also gave attendees a look at what’s coming. Sea-Glass can identify multiple items from a single photo:
“It identified 10 different items, seven of which were itemized and listed out as e-commerce. You could just click one button and all seven would go on your manifest.”
“You can snap a couple photos and be done with it in a matter of seconds,” he added. “It has been a game changer.”
The future of thrift e-commerce isn’t more paper manifests, more manual research, or more one-off training guides. It’s faster, smarter, connected workflows that help teams make better decisions at scale.
A Partner, Not Just a Vendor
Technology decisions in thrift aren’t just about the tool — they’re about who stands behind it.
“It’s not like a vendor. It’s a partner, really. They’re just as excited as we are about our results.”
— Sarah Challender
“I don’t think there’s anything that I asked for that they haven’t delivered.”
— Phil Romano
For Goodwill leaders evaluating new technology, that support matters. pearldive isn’t software dropped into a workflow — it’s a team that listens, improves, and adapts with its customers.
More Value from Every Donation
The webinar made one thing clear: pearldive is helping thrift organizations unlock more value from the donations they already receive.
By helping teams identify high-value items earlier, create stronger listings faster, and scale production with more confidence, pearldive is changing what Goodwill e-commerce teams can accomplish.
For Goodwill organizations, that means more than operational efficiency. It means more revenue for the mission. More opportunity for employees. More value captured from every donation. And a smarter path forward for the secondhand industry.
Learn More About Thrift-Specific AI
Hear all four Goodwill leaders in their own words — the workflows, the numbers, and the questions from other thrift teams.
▶ Watch “Scaling Thrift E-commerce Through AI-Driven Automation” on demand
Ready to see it in your own operation? Get your first 100 pearldive listings free by booking a demo below.