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The Power of Contextual Advertising: Insights from Aaron Woolf of Trendii | #433

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Aaron discusses how Trendii is revolutionising advertising by integrating shopping with editorial content.

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Aaron leads a team of passionate and talented professionals who are on a mission to revolutionise the online shopping experience with their platform Trendii. Trendii is a platform that enables brands to instantly connect their products to image and video content, allowing, creators, platforms and publishers to monetise their content and engage their audiences with contextually relevant and personalised product recommendations.

In this episode of Add To Cart, we are joined by Aaron Woolf from Trendii.



Imagine scrolling through Vogue Living or watching your favourite TV show and being able to buy the items featured with just a click. This is the vision that drives Trendii, reducing friction in the buying process and enhancing consumer engagement.

Trendii is a advertising software platform founded by Aaron Woolf and is making waves by seamlessly integrating product recommendations into editorial content – potentially transforming the way we shop online.

By integrating shopping experiences directly into the media we consume, Trendii is opening up a whole new online sales shopping channel. With clients including Freedom, Myer, Temple & Webster integrated on networks including news.com, Domain and Vogue Living, Trendii is connecting content with relevant advertising.

Aaron Woolf, the founder of Trendii, explains, “We believe people buy based on inspiration. Every period in history has something that sparks a new wave of style, which is then followed by everyone else. Trendii capitalises on this by offering a way to shop directly from the content that inspires you.”

Our big focus over the coming months and years will be TV. There’s a huge opportunity to connect into living rooms and TV shows, making every show a potential storefront.

Aaron Woolf

Connecting inspirational content and advertising


At its core, Trendii is about connecting the content that inspires consumers with products they can purchase instantly purchase. By enabling brands to instantly connect their products to image and video content, allowing, creators, platforms and publishers to monetise their content and engage their audiences with contextually relevant and personalised product recommendations.

Trendii uses their own proprietary artificial intelligence and computer vision to analyse images and videos, and match them with relevant and shoppable products from a network of partners. Their solutions aim to empower ecommerce brands to increase their sales, revenue, retention, and reach, while providing a seamless and enjoyable shopping journey for audiences around the world.

Aaron Woolf, the founder of Trendii, explains, “We believe people buy based on inspiration. Every period in history has something that sparks a new wave of style, which is then followed by everyone else. Trendii capitalises on this by offering a way to shop directly from the content that inspires you.”

Utilising AI to find best content matches

Trendii’s unique approach involves partnering with publishers to integrate product recommendations into their content seamlessly. This includes everything from lifestyle and entertainment sites to fashion and homeware publishers. Aaron highlights the diversity of their partnerships, stating,

“We work with everyone from Nine and Seven to fashion and home-specific content. Wherever there’s an image or video that might inspire someone, Trendii can be there.”

For brands, Trendii offers a dynamic ad network that leverages AI to match products with content. Brands can advertise through Trendii’s network, gaining exposure in premium content environments. This contextual commerce model has proven successful, with impressive engagement metrics, such as 6,000 clicks in a single day during the Met Gala event.

The future of contextual commerce

Looking ahead, Trendii has ambitious plans to expand its reach. Aaron envisions a world where every television becomes a marketplace, allowing consumers to shop directly from their favorite shows. “Our big focus over the coming months and years will be TV. There’s a huge opportunity to connect into living rooms and TV shows, making every show a potential storefront.”

Additionally, Trendii is exploring new verticals such as beauty, automotive, and even paint colors, showcasing the platform’s versatility. Woolf shares an intriguing example: “We matched a silver Motorola phone to a silver dress worn by a celebrity on the red carpet, and it absolutely crushed it. We’re thinking outside the box and excited about these new possibilities.”

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