VP, Performance Creative and Operations (Chicago)

The Aspen Group (TAG) is one of the largest and most trusted retail healthcare business support organizations in the U.S. and has supported over 20,000 healthcare professionals and team members with close to 1,500 health and wellness offices across 48 states in four distinct categories: dental care, urgent care, medical aesthetics, and animal health. Working in partnership with independent practice owners and clinicians, the team is united with a single purpose: to prove that healthcare can be better and smarter for everyone. TAG provides a comprehensive suite of centralized business support services that power the impact of five consumer-facing businesses: Aspen Dental, ClearChoice Dental Implant Centers, WellNow Urgent Care, Chapter Aesthetic Studio, and Lovet. Each brand has access to a deep community of experts, tools and resources to grow their practices, and an unwavering commitment to delivering high-quality consumer healthcare experiences at scale.As a reflection of our current needs and planned growth we are very pleased to offer a new opportunity to join our dedicated team as a VP, Performance Creative and Operations.Job Description:The VP, Performance Creative is an executive 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, with the mandate and visibility to match.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, brand, and marketing leaders, with a direct line of visibility to the C-suite. 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, including budget and resourcing decisions for the function. The work you build and ship will directly influence how many people walk through our doors.Duties & Responsibilities:1. Build and Lead the AI-Powered Creative ModelThis 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 resourcesSelect, implement, and continuously evolve the AI toolset, covering generative design, video production, copy variation, and asset adaptationUse 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 aloneBuild the guardrails and quality standards that keep AI output on-brand and performance-ready across all channels and brand identitiesStay 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, including build-vs-buy and vendor investment decisions2. Own the Creative-to-Performance Feedback LoopPartner with paid media leads and commercial leadership to translate performance signals (CTR, CVR, hook rate, cost per appointment) into creative directionBuild a closed-loop system from brief to launch to iteration, ensuring creative learnings compound across campaigns and channelsCompress creative production cycles without sacrificing quality, bringing a velocity-first mindset to every workflowEstablish review cadences that keep the organization moving fast without sacrificing rigor3. Build Scalable Testing ArchitectureDevelop and own the creative testing roadmap across concept, variable, format, and audience dimensionsLeverage AI to dramatically expand testing volume, running more variables simultaneously than a traditional team could produceBuild SOPs, briefs, and production workflows that drive consistency and speed across brands and channelsMaintain a living research library of hooks, angles, and formats so learnings are accessible and actionable across the organization4. Translate Brand into Performance Across Multiple Brand IdentitiesBe the senior bridge between brand positioning and conversion-optimized creative across a portfolio of distinct consumer brands; neither can be sacrificed for the otherDevelop creative principles and guardrails that let your team, including AI-assisted production, move fast without going off-brandBuild creative that works across the full consumer journey, from awareness through appointment bookingManage creative simultaneously across national and geo-targeted local campaigns for multiple brands5. Multi-Channel Creative LeadershipOwn creative strategy and output across paid social (Meta, TikTok), paid search, digital video, display, and CTVDevelop platform-specific creative that is genuinely native to each channel, not repurposed from a single master assetBalance high-production and lo-fi approaches, including AI-generated formats, knowing when each earns more trust and converts betterManage agency, AI design vendor, and production vendor relationships to supplement and scale in-house output, with direct accountability for vendor spend6. Executive Leadership and Organizational InfluenceOperate as a member of the senior leadership team and a strategic peer to senior commercial, brand, and media executives, not just a creative executorServe as the executive voice for performance creative in C-suite and executive stakeholder conversations, presenting creative performance and forward strategy with clarity and confidenceBuild and develop the performance creative team, including hiring, coaching, and organizational design as the function scales, with accountability for the function's structure and growthOwn resource allocation, vendor strategy, and technology investment decisions for the function at the enterprise levelFrame creative recommendations in terms of business outcomes and ROI, and hold the function accountable to those metrics7. Data Fluency, Not Just Creative InstinctDefine and track the creative KPIs that matter: hook rate, hold rate, CTR, CVR, cost per appointmentUse data to challenge assumptions and build the case for creative investment at the executive levelFind the story in the numbers and use it to drive creative decisions, including decisions about where AI-generated creative is winning or falling shortQualifications:Required12+ years in performance creative, creative strategy, or performance marketing with clear accountability for measurable outcomes8+ years in a senior leadership role, including experience leading through managers across creative, strategy, or production functionsDemonstrated experience operating at the executive level, including regularly presenting to and influencing C-suite stakeholdersDeep hands-on experience with paid digital channels, particularly paid social and paid search, and creative best practices across eachDemonstrated ability to build creative testing frameworks that generate actionable signal at scaleFluency with AI creative tools (generative image, video, copy) and a concrete point of view on deploying them at production scaleExperience building or managing a hybrid internal/external creative model, including AI-native vendors or freelancersComfort reading and interpreting performance data; you find the story in the numbers and use it to drive creative and business decisionsProven track record influencing resource allocation, organizational design, and technology investment decisions at an executive levelStrongly PreferredBackground in retail, retail healthcare, or another appointment- or location-based business modelExperience managing creative simultaneously across multiple distinct brand identities and geo-targeted marketsTrack record building or scaling an in-house performance creative function from an early stage, including standing up the team and operating modelExperience managing agency and production vendor relationships for high-production formats such as CTV or digital videoProven ability to use AI as both a design tool and a production accelerator, with examples of measurable output improvement*This role is onsite 4 days/week in our Chicago office (Fulton Market District)Annual Salary Range: $225,000-$250,000/year, with a generous benefits package that includes paid time off, health, dental, vision, and 401(k) savings plan with match.If you are an applicant residing in California, please view our privacy policy here: Chicago, IllinoisType: Full time