Head of Creative Strategy

Department: Creative

Location: Canada

Description Why This Role Exists Creative is one of the biggest levers in scaling our clients’ paid media performance.

We’re looking for a Head of Creative Strategy to build the people, systems, and operating model that turn creative into a repeatable performance advantage across our portfolio, both in social and display networks.

You’ll lead Creative Strategy and oversee Creative Execution through the Performance Creative Manager, ensuring strategy, production, performance, and learning operate as one connected system.

Key Responsibilities Who We Are Clever Digital Marketing is a performance marketing agency helping large home improvement companies across the US and Canada grow through Paid Social, Paid Search, CRO, and strategic advising.

We manage a large portfolio of accounts, an in-house creative team, and significant monthly ad spend. As we scale, we’re building a stronger creative-strategy function to help clients find new creative winners — and to turn one-off learnings into repeatable systems that compound across every account.

Skills, Knowledge And Expertise What You’ll Do

• Build and lead CDM’s Creative Strategy function, defining the methodologies, standards, and operating system behind how we research, ideate, test, learn, and scale creative.
• Manage Senior Creative Strategists and the Performance Creative Manager.
• Build systems that turn customer, market, and performance data into actionable creative direction.
• Create a cross-account learning system so wins, losses, hypotheses, and insights compound across the portfolio.
• Set and maintain the strategic and creative quality bar across the department, regularly reviewing work and challenging thinking.
• Ensure Creative Strategy and Creative Execution scale together with the right quality, capacity, velocity, prioritization, and feedback loops.
• Build testing frameworks, briefing standards, and learning loops that improve creative performance and decision-making.
• Build training, playbooks, and frameworks that improve creative thinking across Media Buyers and Creative.
• Build AI-enabled workflows that improve research, analysis, creative intelligence, and decision-making.
• Partner closely with Paid Social, CRO, Paid Search, Client Success, and leadership.
• Ensure creative decisions are connected to business outcomes such as Creative Win Rate, CPL, CPS/CPD, lead quality, COM, and account growth.
• Hire and develop future Creative Strategy talent.

**What We’re Looking For**

• Proven experience leading creative strategy or performance creative.
• Experience building or scaling a team, department, or operating system.
• Strong performance-marketing and commercial understanding.
• Strong direct-response and consumer-psychology background.
• Experience building creative testing frameworks, learning systems, and standards.
• Experience managing strategists and/or creative-production teams.
• Strong cross-functional leadership and ability to drive adoption.
• Strong understanding of AI and how to apply it across a team, not just individually.
• Able to operate at portfolio level while still maintaining a strong account-level creative quality bar.
• Clear, decisive communicator who can simplify complexity and turn strategy into action.

**Nice to Have**

• Lead generation or high-ticket services experience.
• Home improvement experience.
• CRO and landing-page testing familiarity.
• UGC, founder-led, or spokesperson-led creative experience.
• Hands-on familiarity with editing or design tools.

**What Success Looks Like**

• CDM consistently introduces genuinely new creative ideas instead of recycling the same concepts and formats.
• Creative iterations are more deliberate, strategic, and evidence-based.
• Media Buyers and editors produce stronger briefs and creative recommendations on their own.
• Learnings are captured, shared, and applied across accounts.
• AI-supported research and creative workflows are adopted department-wide.
• CDM has a repeatable creative-strategy engine that gets stronger with every test.

Benefits Benefits of Working at CDM

• Competitive base salary + performance-based bonuses
• Flexible remote work environment with option for in-person collaboration (Vaughan, ON)
• Group Benefits - Medical, Dental, Vision, RRSP/401k Plan w/matching, more.
• Company-provided MacBook computer
• Home office bu…