Oh What Fun '25 Holiday Drop
CLIENT:
The Well Connected - A Sponsorship Relations Agency
PROBLEM:
As The Well Connected continued to scale its agency work across sponsorships, gifting suites, and brand activations, there was a growing desire to create a moment that wasn’t client-led, sales-driven, or transactional — but instead rooted in community, gratitude, and connection.
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In 2024, the idea for Oh What Fun was conceived as a holiday gifting concept, but timing and capacity limited its execution. Entering 2025, the agency intentionally reduced its own event output to focus on one meaningful, self-produced activation that could:
• Celebrate long-standing brand partners and new discoveries
• Create inclusive gifting without hierarchy or exclusivity
• Demonstrate TWC’s full sponsorship and experiential capabilities in practice
• Strengthen real-life relationships with creators, media, and agency partners
• Spotlight Canadian-owned brands in a high-touch, high-impact way
The initial vision was a curated holiday box delivered directly to recipients’ doors. However, as brand interest surged and participation grew rapidly, logistical challenges emerged — particularly around shipping, weight, and scale — requiring a strategic pivot without compromising the integrity of the experience.
SOLUTION:
The Well Connected reimagined Oh What Fun as a hybrid gifting experience, combining a curated in-person activation with a digital editorial extension.
Over a focused 30-day activation window, TWC:
• Secured 35+ brand partners (98% Canadian-owned)
• Partnered with GiftGuru.ca as the lead box sponsor to bring the packaging concept to life
• Designed a holiday interview-style gift guide, blending product discovery with brand storytelling
• Pivoted from a door-delivered box to an invite-only Cookies & Cocktails Gifting Lounge/Reception
On December 12, 2025, TWC hosted an intimate, private reception in Toronto for 50 curated guests, including:
• 30 content creators and influencers
• 20 agency partners, clients, friends, and long-time collaborators
The experience was intentionally designed to remove traditional gifting-suite barriers. Guests were guided through a walk-around product experience, introduced to each brand, and invited to build their own gift boxes on-site — ensuring every attendee was equally valued and gifted.
Key experiential elements included:
• A curated cookies and cocktails menu
• Brand reps and agency partners on-site for IRL connection
• A portrait and lifestyle content capture area
• Interactive moments designed to encourage conversation, not consumption
To extend reach beyond the room, TWC also:
• Mailed select gift boxes to partners who couldn’t attend
• Launched a community giveaway for one full Oh What Fun Drop
• Distributed the digital gift guide across owned channels
RESULTS;
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The Oh What Fun Holiday Drop successfully delivered on both emotional impact and strategic outcomes:
• 35+ brand partners activated in under 30 days
• 40 in-person attendees, each receiving a curated gifting experience
• 100% of guests gifted, reinforcing TWC’s inclusive philosophy
• 98% Canadian brand representation, strengthening national brand alignment
• Organic social content generated across creators, brands, and agency channels
• Meaningful IRL connections formed between creators, brands, and agency partners
• A reusable, evergreen editorial gift guide extending campaign life beyond the event
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Most importantly, Oh What Fun demonstrated The Well Connected’s ability to:
• Pivot strategically under pressure
• Design experiences that prioritize people over impressions
• Execute sponsorship, gifting, content, and community-building in one cohesive ecosystem
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What began as a simple holiday box evolved into a signature, values-led activation — one that now sets the foundation for future annual drops and agency-owned experiences.
“Oh What Fun started as a simple idea about gifting—but it quickly became a reminder that connection is the real currency. We didn’t want to create another moment of consumption; we wanted to create a space where people felt seen, valued, and genuinely connected. Watching brands, creators, and partners meet in real life—many for the first time—was exactly the outcome we hoped for.”
— Jacquelene Clarke, Founder, The Well Connected
Aligned Sponsors 2025
Event Gallery
Photo Credit: Frodillah
Holiday Gift Guide
Oh What Fun Holiday Gift Guide 2025
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A curated companion to the Holiday Drop experience, this interview-style guide spotlights 35+ incredible brands that helped make this season brighter. From beauty to beverage, wellness to indulgence—each feature tells the story of connection, creativity, and community.
Whether you joined us IRL or are unwrapping your drop at home, consider this your festive passport into our world of joyful gifting.
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Click to read our guide! >>>
Video Recap
Video Credit: Eboni McDonald