Creative Lead, Brand Experience

Caseware•Toronto, ON

2d•Hybrid

About The Position

Caseware is seeking a Lead Creative, Brand & Experience to lead and evolve its creative function at the intersection of brand, data, and AI-driven innovation. This role is for a creative leader who shapes how the brand shows up, stands out, and scales, understanding that creativity today involves art, intelligence, insights, performance data, and AI tools. This is an existing, full-time, permanent position. It is a hybrid role requiring three days a week at the Toronto office.

Requirements

8+ years of experience in creative services, design leadership, or creative operations
Proven ability to lead creative teams in a fast-paced, multi-stakeholder environment
Strong understanding of AI tools and their application in creative workflows
Experience using data and performance insights to guide creative decisions
A balance of strategic thinking and hands-on execution
Excellent communication and stakeholder management skills

Nice To Haves

You see AI as an enabler of creativity, not a replacement
You are as comfortable discussing creative concepts as you are performance metrics
You bring a mindset of continuous improvement and experimentation
You understand how to scale creativity without sacrificing quality

Responsibilities

Lead the development and delivery of high-quality creative across digital, campaigns, events, and brand initiatives.
Ensure all creative outputs align with brand standards, messaging, and strategic objectives.
Translate complex business and product concepts into compelling visual and narrative experiences.
Act as a brand guardian and innovator, ensuring consistency while continuously evolving how we show up.
Integrate AI tools into the creative workflow (generative design, content automation, ideation).
Identify opportunities to improve speed, scale, and personalization through AI.
Stay ahead of emerging technologies and bring forward new ways of working.
Leverage performance data, audience insights, and analytics to inform creative direction.
Partner with the broader marketing organization to optimize creative effectiveness.
Establish feedback loops to continuously improve creative based on results.
Lead, mentor, and inspire a team of designers, producers, and external partners.
Build a high-performing creative function that balances craft, speed, and scalability.
Oversee intake, prioritization, and resource allocation across multiple stakeholders.
Implement modern workflows that enable agility without compromising quality.
Partner closely with product marketing, brand, demand generation, and events teams.
Act as a strategic advisor, not just an execution partner, in campaign and content planning.
Ensure creative is integrated early in the go-to-market process.
Optimize tools, systems, and workflows that support creative production.
Champion scalable design systems, templates, and asset management.
Drive operational excellence across the creative function.