What Would You Do as Head of eCommerce Entering the Preloved Market? – with Andy Ostcliffe (episode 605)
Andy Ostcliffe is the Chief at Chiefly, where they’re experts on the Charity Retail Sector and pre-loved sales across product categories. Previously Andy co-created and led two of the world’s largest charity online retailers – Oxfam and British Heart Foundation.
Andy joins Chloe for a What Would You Do? episode, exploring what today’s Head of eCommerce should do if their fashion brand wants to enter the growing pre-loved market. Together, they unpack the operational, commercial, and regulatory challenges, and discuss how brands can build a strategy that works for both customers and the business.
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Dive in:
[04:38] Retailers and preloved fashion trends
[06:28] Challenges in retail logistics
[09:35] Economic challenges for PLC retailers
[13:03] Impact of Secondhand Sales
[16:55] UK charity shops and new regulations
[21:16] Impact of Online Resale on Charities
[23:29] Ghana’s role in pre-loved fashion
[29:29] Pricing and stock rotation strategies
[31:00] Retail strategy for preloved fashion
[35:31] Listen to Andy’s Top Tips!
Build a Resale Strategy Before You Build a Resale Store
Selling pre-loved products is not as simple as adding another category to your website. Every item is unique, which changes everything from photography and merchandising to fulfilment and customer service. Andy explains why resale is an entirely different business model from selling new products. For many brands, partnering with an established resale platform may be a smarter first step than building everything in-house. If you’re considering resale, start by understanding the operational challenges before investing in the technology.
Look Beyond Profit and Think About Long-Term Value
The resale market isn’t just about creating another revenue stream. It can also strengthen customer loyalty, improve lifetime value, and help prepare your business for future regulations. Chloe and Andy discuss why the financial return should be measured across the whole customer relationship, not just the resale transaction itself. A well-designed buyback or trade-in programme can keep customers engaged with your brand for longer. The brands that see resale as part of a bigger strategy are likely to gain the greatest advantage.
Prepare Now for the Regulations That Are Coming
Future legislation will require brands to take greater responsibility for what happens to their products after they are sold. Andy explains how Extended Producer Responsibility and Digital Product Passports will change the way fashion brands operate. Businesses will need to track where garments go, how they are reused, and when they are eventually recycled or disposed of. That means collecting better data throughout the product lifecycle. Preparing now could give brands a significant head start when these requirements become standard.
Use AI to Make Resale Commercially Viable
One of the biggest barriers to resale has always been the time it takes to process individual products. Andy explains how AI is already transforming that process by helping teams identify garments, create listings, and capture product details much faster. In some operations, AI has increased listing productivity from around 40 items per person each day to more than 200. That kind of efficiency could completely change the economics of resale. As AI continues to improve, it may become one of the biggest enablers of circular commerce.
Let Data Become Your Competitive Advantage
Andy believes the biggest opportunity in resale isn’t the clothing itself—it’s the data behind it. Brands that can accurately track every product through its lifecycle will be better prepared for future compliance and better equipped to improve their business. Data will help businesses understand customer behaviour, measure the success of resale programmes, and report on sustainability efforts. It will also make it easier to decide what should be resold, recycled, or retired. In the future, the brands with the best data may be the ones that lead the market.
eCommerce Book Top Tip
- Read something unrelated to business. Give your mind a break with fiction or a book that makes you laugh and think.
eCommerce Traffic Top Tip
- Experiment with live shopping to showcase products, engage customers in real time, and unlock higher sales.
Tool Top Tip
- Use AI to quickly research information and generate insights that help you make better decisions.
Carbon Top Tip
- Encourage customers to reuse the original packaging for returns or take-back schemes to reduce packaging waste.
Interview links
Related Episodes
- WWYD? Ian Leslie on Achieving Hockey Stick Growth in a $10–25M eCommerce Brand (episode 561)
- What Would You Do if growth at your eCommerce brand has stalled? – with Janis Thomas (episode 566)
- What Would You Do as Head of eCommerce tasked with massively improving operational efficiency? – with Jaime Hill (episode 570)
- What Would You Do to Tackle the Opportunity that is AI Chat and GEO? – with Miracle Inameti-Archibong (episode 578)
- What Would You Do if you were embarking on a replatform in 2026? – with James Gurd (episode 584)
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