Pinterest’s “Think Outside the Box” SMB Holiday Event by The Event Agency

The holiday season hit early at Pinterest’s Toronto headquarters last summer, when the space was transformed into a festive, high-touch environment for the company’s annual SMB Holiday Event. Produced by The Event Agency, the gathering brought together advertisers and small business marketers for an immersive “Think Outside the Box” experience that showed, rather than told, how to use Pinterest to drive seasonal campaigns.

Instead of a standard B2B update, the goal was to turn Pinterest’s value proposition into something attendees could see, touch, taste, and share. The Event Agency handled full-service production, encompassing creative design, holiday styling, technical execution, and on-site management, to build an environment that felt like scrolling through a perfectly curated Pinterest board brought to life.

The transformation of the HQ began with Pinterest-branded installations that carried the theme through every corner of the space. A Holiday-Inspired Photo Op became a natural content hub, while a Custom Pinterest Mailbox quickly emerged as the hero activation. Guests chose from branded card designs, wrote personal messages, addressed them, and dropped them in the mailbox, where “elves” promised to handle postage. It was playful, simple, and perfectly on-theme: connection, personalization, and thinking beyond the usual holiday networking moment.

Behind the scenes, logistics and vendor management were dialled in to support that elevated feel. Catering featured a custom cocktail experience and a branded hot chocolate station by Soho Sweet Cart, complete with logo’d marshmallows and custom cups that kept the Pinterest identity in every photo. Large prints by Event Graffiti anchored the visual story, while props and décor from Glamorous Affairs added texture and warmth to the space. Moxo Media provided the custom cards and Pinterest-branded ornaments, tying the stationery and take-home elements back to the platform’s discovery-driven brand.

The gifting display extended that story by highlighting local small businesses, subtly reinforcing Pinterest’s role in surfacing creators and makers. Every touchpoint, visual, tactile, and digital, worked together to demonstrate how a strong creative theme can become a strategic sales tool.

Programming mixed actionable advertising content with these sensory experiences, so learning never felt separate from the environment. Attendees didn’t just hear about how to “think outside the box” with holiday campaigns; they moved through it, interacted with it, and took pieces of it home.

The response underscored the impact:

“Thanks so much to this entire group for flawlessly executing yesterday’s event! Our clients and teams couldn’t stop talking about the amazing festive decor, snacks and drinks. It really got everyone thinking about the holidays!”

For planners, the Pinterest SMB Holiday Event is a prime example of strategic event production: start with a clear theme aligned with the brand story, then build a cohesive experience where every element, content, catering, installations, and gifting, pulls in the same direction. The result was more than a mid-summer holiday party; it was a memorable B2B experience that turned Pinterest’s seasonal messaging into something guests could feel, share, and act on.