Paid Media Specialist (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 by 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 Pet Health Care. 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 Clear Choice team as a Paid Media Specialist.

About the Role:

We are looking for a curious, analytical, and highly accountable paid media professional to support the management and optimization of a large-scale performance marketing program.

This role will work across paid search, paid social, and other digital acquisition channels, partnering closely with internal marketing teams, agencies, analytics partners, and business stakeholders.

While hands-on experience with paid search or paid social is important, success in this role requires more than platform expertise. We are looking for someone who wants to understand how the business works , can connect multiple data points to determine what is actually happening, and is comfortable moving beyond reporting metrics to explaining why performance changed and what we should do about it .

The ideal candidate is naturally curious, takes ownership without waiting for a task list, and consistently looks for opportunities to improve performance, processes, and decision-making.

Responsibilities:

• Support the day-to-day management and strategic oversight of paid search, paid social, and other performance marketing channels.
• Analyze performance across the entire customer funnel rather than evaluating advertising platforms in isolation.
• Investigate performance changes by triangulating multiple signals, including media metrics, conversion behavior, lead quality, scheduling activity, downstream outcomes, tracking changes, landing-page changes, and broader business trends.
• Translate data into a clear point of view: What happened? Why did it happen? Does it matter? What should we do next?
• Identify opportunities, risks, and anomalies proactively rather than waiting for them to be assigned.
• Develop recommendations around budget allocation, channel mix, campaign strategy, testing, targeting, landing pages, and measurement.
• Partner with media agencies while maintaining strong internal ownership of performance and strategy.
• Challenge agency recommendations when appropriate and ensure decisions are grounded in business outcomes rather than platform metrics alone.
• Monitor testing and changes across the organization that could impact paid media performance and help ensure appropriate stakeholders are informed.
• Work closely with analytics and measurement partners to understand attribution, conversion tracking, offline conversion data, and other signals used to evaluate media effectiveness.
• Communicate findings clearly and concisely to both technical and non-technical stakeholders.
• Maintain a strong understanding of current initiatives, priorities, tests, and performance drivers across the business.
• Help build repeatable processes, reporting, documentation, and analysis that make the broader team more effective.
• Develop expertise across additional media channels over time and take on increasing ownership as the role grows.

Requirements:

• Experience working in paid search, paid social, or another performance marketing discipline.
• Strong analytical instincts and comfort working with large or imperfect datasets.
• Ability to move beyond surface-level observations and investigate the underlying drivers of performance.
• Demonstrated ability to connect data from multiple sources to develop a complete view of a business problem.
• Strong sense of ownership and accountability.
• Intellectual curiosity and a genuine desire to understand how and why things work.
• Ability to operate effectively when a problem does not have an obvious answer or predefined set of steps.
• Strong written and verbal communication skills.
• Comfort asking questions, challenging assumptions, and developing an independent point of view.
• Ability to prioritize work based on business impact rather than simply completing assigned tasks.
• Collaborative mindset and willingness to learn.

Preferred:

• Experience with Google Ads, Microsoft Advertising, Meta Ads, or similar platforms.
• Experience working with external media agencies.
• Familiarity with conversion tracking, offline conversions, attribution, CRM or first-party data.
• Experience managing or analyzing significant digital media budgets.
• Experience in a lead-generation or performance marketing business where media success depends on downstream customer actions.
• Exposure to experimentation, landing-page optimization, or conversion-rate optimization.

What Success Looks Like:

Success in this role is not measured by how many reports you produce or how many tasks you complete.

Successful team members:

• Own outcomes, not assignments.
• Notice when something does not make sense and investigate it.
• Understand the difference between correlation and causation.
• Look at multiple sources of information before reaching a conclusion.
• Connect media performance to what is happening in the actual business.
• Bring recommendations, not just observations.
• Know when something is materially important and when it is noise.
• Communicate proactively when they uncover a risk or opportunity.
• Learn from feedback quickly and apply it to the next problem.
• Become increasingly independent and require less direction over time.

Most importantly, we are looking for someone who sees a performance change and instinctively wants to understand why .

Annual Salary Range : $75,000-$100,000, with a generous benefits package that includes paid time off, health, dental, vision, and 401(k) savings plan with match