Director Creative Strategy Jobs in Toronto, ON (NOW HIRING)

Senior Creative Director – DTC eCommerce (Whisky Library)

About the Role

We’re looking for a Senior Creative Director to own and drive the creative strategy for Whisky Library across paid and organic channels. This is a hands-on, high-ownership role focused on developing creative concepts, messaging, hooks, and content strategies that drive brand growth and customer acquisition.

You’ll report directly to our leadership team and work closely with our editors and content creators to turn creative strategies into high-performing content. You’ll be responsible for bringing strong ideas to the table, providing clear creative direction, and continuously improving our creative based on performance and market insights.

This is a collaborative individual contributor role, not a people-management position. We’re looking for someone who can operate independently, take ownership of the creative strategy, and work closely with the team to execute at a high level.

Who We Are

We are Whisky Library, a U.S.-based whiskey retail and subscription company building a modern way to discover and purchase bourbon. The whiskey industry has remained largely unchanged for decades, and our mission is to meaningfully improve how people explore, learn about, and buy whiskey online.

We’re a small, global, execution-driven team that values ownership, speed, creativity, and high-quality output over process or hierarchy.

What You’ll Do

• Creative Strategy

  • Own creative strategy across paid and organic social

  • Develop creative concepts, hooks, angles, messaging, and content ideas

  • Research customers, competitors, trends, and winning creative to identify new opportunities

  • Create clear creative briefs and direction for editors and creators

  • Develop testing strategies to improve creative performance continuously

• Paid & Organic Creative

  • Develop creative strategies that work across both paid advertising and organic content

  • Identify trends, formats, and creative angles that can be adapted for the Whisky Library audience

  • Find opportunities to turn strong organic concepts into paid creative and vice versa

  • Stay current with what is working across Meta, TikTok, Instagram, and other social platforms

  • Continuously test and develop new creative approaches

• Collaboration & Execution

  • Work directly with leadership, editors, and creators to bring creative concepts to life

  • Provide clear and actionable creative direction and feedback

  • Review creative and ensure the final output aligns with the strategy

  • Analyze creative performance and use insights to guide future concepts

  • Take ownership of creative strategy from concept through execution

What We’re Looking For

• Required Qualifications

  • Strong background with DTC, eCommerce, consumer, or social-first brands

  • Deep understanding of direct-response advertising and performance creative

  • Strong copywriting, messaging, and concept development skills

  • Proven ability to develop creative strategies for paid social

  • Strong understanding of organic social content and current creative trends

  • Data-driven mindset with a strong understanding of creative performance

  • Ability to work independently in a small, fast-moving team

• Preferred Qualifications

  • Background in developing creative strategies across both paid and organic social

  • Skills in UGC, creators, influencers, and short-form video

  • Strong understanding of Meta, TikTok, Instagram, and other social platforms

  • Track record of working directly with video editors and content creators

  • Passion for studying high-performing ads and continuously improving creative

Success in This Role

You’ll succeed if you:

• Consistently develop creative concepts that improve business performance

• Build a strong creative strategy across paid and organic channels

• Give editors and creators clear direction that results in high-quality content

• Use data and performance insights to continuously improve creative

• Stay ahead of trends and identify new creative opportunities

• Take full ownership of creative strategy and execution

Why Join Us?

• High-impact role with direct influence on growth and creative direction

• Work directly with leadership, editors, and creators

• Small, fast-moving team with significant autonomy

• Opportunity to shape the creative strategy of a growing DTC brand

• No unnecessary layers of management or bureaucracy

If you’re a senior creative strategist who understands what makes content get attention, what makes people take action, and how to turn creative ideas into measurable business results, we’d love to hear from you.