Creative Landscaping In Jobs in Chicago, IL (NOW HIRING)

TheAspenGroup(TAG)isoneofthelargestandmosttrustedretailhealthcarebusinesssupportorganizationsintheU.S.andhassupportedover20,000healthcareprofessionalsandteammemberswithcloseto1,500healthandwellnessofficesacross48statesinfourdistinctcategories:dentalcare,urgentcare,medicalaesthetics,andanimalhealth.Workinginpartnershipwithindependentpracticeownersandclinicians,theteamisunitedwithasinglepurpose:toprovethathealthcarecanbebetterandsmarterforeveryone.TAGprovidesacomprehensivesuiteofcentralizedbusinesssupportservicesthatpowertheimpactoffiveconsumer-facingbusinesses:AspenDental,ClearChoiceDentalImplantCenters,WellNowUrgentCare,ChapterAestheticStudio,andLovet.Eachbrandhasaccesstoadeepcommunityofexperts,toolsandresourcestogrowtheirpractices,andanunwaveringcommitmenttodeliveringhigh-qualityconsumerhealthcareexperiencesatscale.

AsareflectionofourcurrentneedsandplannedgrowthweareverypleasedtoofferanewopportunitytojoinourdedicatedteamasaSrDirector,PerformanceCreative.

JobDescription:

The Sr Director, Performance Creative is a senior leadership role with enterprise-wide accountability for the creative engine behind our paid media program, spanning paid social, paid search, digital video, display, and connected TV. This is not a functional manager position. This is an executive owner of one of the most consequential levers in our growth model.

This person will define what AI-powered performance creative looks like at TAG, set the organizational standard for how creative is built, scaled, and evaluated, and operate as a strategic peer to our most senior commercial and marketing leaders. The core challenge is simple to state and hard to solve: we need an order of magnitude more creative output, engineered for performance from the first pixel. AI is the answer to that challenge, and this role is the one who wires it in.

You will architect and lead a hybrid model of internal creatives and external AI-native designers, build the systems and team that sustain it, and own the results. The work you build and ship will directly influence how many people walk through our doors.

Core Responsibilities:

1. Build and Lead the AI-Powered Creative Model

This is the defining responsibility of the role. AI is not a tool to dabble in here, it is the production infrastructure.

• Architect a hybrid creative organization: internal creative strategists and brand-literate designers working in concert with a curated bench of external AI-native designers and production resources

• Select, implement, and continuously evolve the AI toolset, covering generative design, video production, copy variation, and asset adaptation

• Use AI as a design tool, a production accelerator, and a testing multiplier, enabling the team to produce at a volume and iteration speed that would be impossible through traditional production alone

• Build the guardrails and quality standards that keep AI output on-brand and performance-ready across all channels and brand identities

• Stay ahead of the AI creative landscape and bring a sharp, informed point of view to the C-suite on where the category is headed and what to adopt next

2. Own the Creative-to-Performance Feedback Loop

• Partner with paid media leads and commercial leadership to translate performance signals (CTR, CVR, hook rate, cost per appointment) into creative direction

• Build a closed-loop system from brief to launch to iteration, ensuring creative learnings compound across campaigns and channels

• Compress creative production cycles without sacrificing quality, bringing a velocity-first mindset to every workflow

• Establish review cadences that keep the organization moving fast without sacrificing rigor

3. Build Scalable Testing Architecture

• Develop and own the creative testing roadmap across concept, variable, format, and audience dimensions

• Leverage AI to dramatically expand testing volume, running more variables simultaneously than a traditional team could produce

• Build SOPs, briefs, and production workflows that drive consistency and speed across brands and channels

• Maintain a living research library of hooks, angles, and formats so learnings are accessible and actionable across the organization

4. Translate Brand into Performance Across Multiple Brand Identities

• Be the senior bridge between brand positioning and conversion-optimized creative across a portfolio of distinct consumer brands; neither can be sacrificed for the other

• Develop creative principles and guardrails that let your team, including AI-assisted production, move fast without going off-brand

• Build creative that works across the full consumer journey, from awareness through appointment booking

• Manage creative simultaneously across national and geo-targeted local campaigns for multiple brands

5. Multi-Channel Creative Leadership

• Own creative strategy and output across paid social (Meta, TikTok), paid search, digital video, display, and CTV

• Develop platform-specific creative that is genuinely native to each channel, not repurposed from a single master asset

• Balance high-production and lo-fi approaches, including AI-generated formats, knowing when each earns more trust and converts better

• Manage agency, AI design vendor, and production vendor relationships to supplement and scale in-house output

6. Senior Leadership and Organizational Influence

• Operate as a strategic peer to senior commercial, brand, and media leaders, not just a creative executor

• Present creative performance and forward strategy to C-suite and executive stakeholders with clarity and confidence

• Build and develop the performance creative team, including hiring, coaching, and organizational design as the function scales

• Influence resource allocation, vendor strategy, and technology investment decisions at the enterprise level

• Frame creative recommendations in terms of business outcomes and ROI, and hold the function accountable to those metrics

7. Data Fluency, Not Just Creative Instinct

• Define and track the creative KPIs that matter: hook rate, hold rate, CTR, CVR, cost per appointment

• Use data to challenge assumptions and build the case for creative investment at the executive level

• Find the story in the numbers and use it to drive creative decisions, including decisions about where AI-generated creative is winning or falling short

Experience and Qualifications:Required

• 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

Strongly Preferred

• 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

AnnualSalaryRange:$195,000-$230,000/year,withagenerousbenefitspackagethatincludespaidtimeoff,health,dental,vision,and401(k)savings planwithmatch.

IfyouareanapplicantresidinginCalifornia,pleaseviewourprivacypolicyhere:https://careers.aspendental.com/us/en/tag-privacy-policy-for-california-employees