Sr Director, Performance Creative

The Aspen Group•Chicago, IL

About The Position

The Aspen Group (TAG) is a leading retail healthcare business support organization. This role is a senior leadership position with enterprise-wide accountability for the creative engine behind our paid media program, covering paid social, paid search, digital video, display, and connected TV. The position is responsible for defining AI-powered performance creative, setting organizational standards for creative development, scaling, and evaluation, and collaborating with senior commercial and marketing leaders. The core challenge is to significantly increase creative output engineered for performance, leveraging AI as the primary solution. This role will architect and lead a hybrid model of internal creatives and external AI-native designers, build the necessary systems and team, and be accountable for the results, directly influencing customer acquisition.

Requirements

10+ years in performance creative, creative strategy, or performance marketing with clear accountability for measurable outcomes.
5+ years in a senior leadership role with direct reports across creative, strategy, or production functions.
5+ years of in-house (client-side) marketing experience, with direct ownership of strategy and execution, partnering cross-functionally to deliver measurable business results.
Demonstrated experience operating at or near the executive level, including presenting to and influencing C-suite stakeholders.
Deep hands-on experience with paid digital channels, particularly paid social and paid search, and creative best practices across each.
Demonstrated ability to build creative testing frameworks that generate actionable signal at scale.
Fluency with AI creative tools (generative image, video, copy) and a concrete point of view on deploying them at production scale.
Experience building or managing a hybrid internal/external creative model, including AI-native vendors or freelancers.
Comfort reading and interpreting performance data; you find the story in the numbers and use it to drive creative and business decisions.
Proven ability to influence resource allocation, organizational design, and technology investment decisions.

Nice To Haves

Background in retail, retail healthcare, or another appointment- or location-based business model.
Experience managing creative simultaneously across multiple distinct brand identities and geo-targeted markets.
Track record building or scaling an in-house performance creative function from an early stage.
Experience managing agency and production vendor relationships for high-production formats such as CTV or digital video.
Proven ability to use AI as both a design tool and a production accelerator, with examples of measurable output improvement.

Responsibilities

Build and Lead the AI-Powered Creative Model: Architect a hybrid creative organization (internal strategists/designers and external AI-native designers/production resources), select and evolve AI tools for generative design, video production, copy variation, and asset adaptation, use AI as a design tool, production accelerator, and testing multiplier, build guardrails for on-brand and performance-ready AI output, and stay informed on AI creative landscape advancements.
Own the Creative-to-Performance Feedback Loop: Partner with paid media and commercial leadership to translate performance signals into creative direction, build a closed-loop system from brief to launch to iteration, compress creative production cycles while maintaining quality, and establish review cadences for speed and rigor.
Build Scalable Testing Architecture: Develop and own the creative testing roadmap across concept, variable, format, and audience, leverage AI to expand testing volume, build SOPs, briefs, and production workflows for consistency and speed, and maintain a living research library of hooks, angles, and formats.
Translate Brand into Performance Across Multiple Brand Identities: Act as a senior bridge between brand positioning and conversion-optimized creative for a portfolio of distinct consumer brands, develop creative principles and guardrails for AI-assisted production, build creative for the full consumer journey, and manage creative for national and geo-targeted local campaigns.
Multi-Channel Creative Leadership: Own creative strategy and output across paid social, paid search, digital video, display, and CTV, develop platform-native creative, balance high-production and lo-fi approaches, and manage agency, AI design vendor, and production vendor relationships.
Senior Leadership and Organizational Influence: Operate as a strategic peer to senior leaders, present creative performance and strategy to C-suite stakeholders, build and develop the performance creative team, influence resource allocation, vendor strategy, and technology investment, and frame creative recommendations in terms of business outcomes and ROI.
Data Fluency, Not Just Creative Instinct: Define and track creative KPIs, use data to challenge assumptions and justify creative investment, find the story in the numbers to drive creative decisions, and identify areas where AI-generated creative is succeeding or falling short.