Halloween Campaign 2024: Piloting Collaborative Creative Under Pressure

Role: Senior Digital Designer & Concept Lead

Timeline: July 2024 – October 2024 (3-4 months from concept to launch), utilized again for 2025 season

Campaign Performance: +4% revenue YoY, +4.3% visits YoY

Context: First pilot of collaborative campaign concepting at Total Wine & More

The Setup

Total Wine had always approached major seasonal campaigns the same way: draw names from a hat, let one designer own the entire concept, execute across all channels. For Halloween 2024, leadership wanted to test something different—collaborative concepting where multiple designers would contribute to one chosen vision.

Simple enough, except we'd never done this before. No established protocols. No precedent. Just four designers developing individual concepts, one would get chosen, and then that person would somehow coordinate everyone else to bring it to life.

I won the concept lottery. Now I had to figure out how to art direct three other designers (including people more senior than me) while keeping the creative vision intact and stakeholders across multiple departments happy.

The Brief Nobody Finished

The initial campaign brief left more questions than answers. Target audience? Vague. Channel priorities? Unclear. Strategic focus beyond "make it Halloween-y"? Missing.

Rather than just wing my concept and hope for the best, I followed up with the brief creators and worked with senior design managers to nail down specifics.

What started as clarifying questions for my own concept became improvements that helped all four designers develop stronger proposals.

For my pitch to the VP of Creative Operations, I did my homework. I pulled previous Halloween campaigns from the past 2.5 years and showed how my concept could adapt to real marketing strategies—"Pumpkin Beer" focus areas, "Scary Delicious Reds" product groupings, proven channel approaches. I wasn't just presenting pretty mockups; I was demonstrating strategic integration with established patterns.

My concept got selected. Time to figure out this whole art direction thing.

Managing Peers Without Formal Authority

Here's where it got interesting. I needed to coordinate:

• Two designers on the signage/print team (one senior designer, one lead designer—both technically above my level)

• One mid-level digital designer who was new to the team

No formal reporting structure. No established workflows for collaboration. Just "make this work" and a pre-scheduled vacation I'd booked before any of this started.

The key was establishing clear creative direction while leaving room for individual contributions. We collaboratively developed the color palette, refined typography applications, and created iconography that incorporated elements from everyone's original concepts. People weren't just executing someone else's vision—they were genuinely contributing to it.

I coordinated with the copy team for messaging, prepared talking points for the big stakeholder review, and made sure everyone understood the strategic rationale behind creative decisions. Then I went on vacation for a week, trusting the team to keep momentum without me micromanaging every detail.

Three Decks, Three Audiences

Different stakeholders needed different information. I created three distinct communication strategies:

Creative Team Deck: ADA compliance specs (including specific contrast ratios), icon libraries with usage guidelines, font sourcing for non-Adobe CC typefaces, typography treatment rules. Basically, "here's everything you need to execute this consistently."

Marketing Leadership Deck: Strategic rationale, copy examples, channel applications, and a whole section on ADA compliance thinking to get ahead of their typical color feedback. I may have mentioned recent Total Wine lawsuits over accessibility issues. That particular talking point worked remarkably well.

Digital Merchandising Brief: Process transparency about what we were building and why. At the time, we didn't have a Web & Display manager, so communication between departments was rough. I wanted to show Digital Merchandising our thinking early, respect their performance KPIs, and find ways to balance their lifestyle photography preferences with Marketing's illustration love.

The Dark Palette Problem

Halloween aesthetic demanded it: dark gray and cream as primaries, neon green, vibrant purple, and bright orange as accents. Perfect for spooky vibes. Terrible for wine bottles, which are predominantly dark glass.

We solved it through layered iconography and establishing cream background standards with complementary "spooky" illustrations. Product visibility maintained, Halloween aesthetic preserved, ADA compliance achieved. Sometimes constraints make you more creative.

Real-Time Optimization

During October execution, I stayed connected with Digital Product Analytics to track performance. When data showed opportunities, we made adjustments:

• Week 40: Halloween visits down 38% YoY initially, but conversion rate up 430 basis points and revenue flat. Not panicking—watching.

• Week 41: Added Jose Cuervo Devil's Tequila creative and Prisoner's Cabernet to landing pages based on competitive analysis. Campaign starting to climb: +9% visits, +17% revenue YTD.

• Week 42: Peak week performance: +110% visits week-over-week, +181% revenue week-over-week.

• Week 43-44: Final results: +4.3% visits YoY, +4% revenue YoY. Top creative module drove $61K in revenue.

I wasn't just tracking numbers—I was building relationships with the analytics team that enabled these optimizations. That practice has since become standard for major campaigns.

Results: Process That Stuck

The collaborative approach worked better than previous solo-designed campaigns, and the organization took notice. The framework we piloted became the standard for major seasonal campaigns going forward.

Performance:

• Revenue: +4% year-over-year

• Visits: +4.3% year-over-year

• Peak week: +181% revenue week-over-week

• Top module: $61K revenue from "Spooky Spirits" creative

Organizational Impact:

• Established reusable creative toolkit (color systems, typography standards, icon libraries, ADA-compliant templates)

• Improved Marketing/Digital Merchandising working relationship

• Created scalable process for future collaborative campaigns

• Demonstrated that illustration/lifestyle hybrid approach could satisfy both teams' preferences

Process Innovation: Going back for performance data wasn't standard practice—I just needed to understand what worked. That initiative turned into documented lessons learned that informed Halloween 2025 planning: expand color palette beyond dark gray/cream, add more diverse iconography, lean harder into lifestyle/illustration balance.

Lessons in Collaborative Project Management

Informal leadership requires different skills: Art directing peers without formal authority meant establishing creative credibility, building genuine collaboration, and trusting people to execute without micromanagement.

Proactive clarification prevents downstream chaos: Strengthening the brief upfront helped everyone, not just my concept. Small time investment, significant efficiency gains.

Stakeholder communication isn't one-size-fits-all: Three different audiences needed three different approaches. Tailoring communication to specific needs and priorities prevented confusion and reduced revision cycles.

Performance tracking creates competitive advantage: Building relationships with analytics teams enabled optimization that directly impacted business results. Numbers informed decisions, decisions improved outcomes.

Process innovation beats perfect execution: The collaborative approach had rough edges, but proving the concept worked mattered more than flawless implementation. We iterated and improved for next year.

If I were managing this project today, I'd establish clearer role definitions upfront, create more structured check-in cadences, and document the collaborative process more thoroughly for future teams. But the fact that this approach became the standard practice suggests we got the important parts right.