SVP, Artificial Intelligence Strategy and Operations

The Aspen Group; Chicago (IL); On-site; USD 180,000 - 260,000; Full time

Job summary

The Aspen Group (TAG) seeks a commercially oriented AI and transformation leader to bridge strategy and execution across a multi-brand healthcare enterprise. You will shape AI and automation roadmaps, evaluate vendor solutions, and translate complex capabilities into executive decisions.

You will build governance, partner with HR and L&D for workforce readiness, and lead cross-functional teams to deliver measurable outcomes across Aspen Dental, WellNow, Chapter Aesthetic Studio, and Lovet Pet

Qualifications

• 10+ years of strategy, transformation, technology, or analytics roles with growth.
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Responsibilities

• Lead and manage the AI & innovation portfolio strategy and pipeline to deliver measurable outcomes.
• Align AI portfolio to business strategy and advise executives on prioritization and ROI.
• Develop and maintain an enterprise AI governance framework, execution roadmap, and KPI dashboard.
• Act as an AI advocate across TAG's brands and functions.
• Partner with business leaders to prioritize AI/RPA/automation across the portfolio.
• Lead change management with HR and L&D for workforce readiness.
• Monitor healthcare/dental landscape and engage with external vendors for AI tech.
• Evaluate, customize, and integrate vendor AI/RPA solutions with IT/PMO.
• Represent TAG as an AI thought leader and data-driven advocate.
• Frame complex choices for executive decision-making with clear options.

Skills

AI/ML familiarity

Data analytics

Automation tools

RPA

GenAI

Executive communication

Cross-functional leadership

Strategy development

Portfolio management

Vendor evaluation

Education

Master's degree (MBA, MS in Analytics, CS, or related)

Job description

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 22,000 healthcare professionals and team members at more than 1,400 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.

The Opportunity

We are seeking a commercially-oriented AI and transformation leader who can bridge strategy and execution across a complex, multi-brand healthcare enterprise. The ideal candidate brings a track record of defining and delivering AI/data-driven transformation programs — whether from a top-tier consulting firm, a PE-backed portfolio environment, a large-scale tech/SaaS platform, or a senior transformation role within a complex operating company. This leader must be equally adept at building a compelling business case and rolling up their sleeves to drive results through cross-functional teams.

Deep technical AI expertise is not required, but applied familiarity with AI/ML, data analytics, and automation tools is essential — enough to evaluate vendor solutions critically, partner credibly with technical teams, and translate complex capabilities into clear executive decisions. This role demands strong operating instincts, the ability to navigate ambiguity inside a large organization, and a bias toward measurable outcomes.

Responsibilities

• Lead and manage the AI & innovation portfolio strategy and pipeline. Understand customer and business needs to recommend solutions where AI may be optimal — to create efficiencies, drive growth, unlock employee potential, and improve compliance.
• Align AI portfolio to business strategy and outcomes. Provide recommendations to executive leadership on how to prioritize initiatives and identify the most concrete, high-ROI business cases.
• Develop and maintain an enterprise AI governance framework, execution roadmap, and KPI dashboard. Drive portfolio reporting to senior leadership with clarity and accountability.
• Act as an AI advocate — sharing best practices, learnings, and emerging capabilities across TAG's brands and functional teams.
• Partner with business functional leaders to understand their challenges and prioritize AI/RPA/automation solutions that unlock performance. Build durable working relationships across the portfolio.
• Lead change management: partner with HR and L&D to build workforce readiness, upskilling programs, and adoption strategies for new AI technologies.
• Continuously monitor the healthcare and dental competitive landscape; engage with external vendor partners to surface emerging AI technologies relevant to TAG's strategy.
• Evaluate, customize, and integrate vendor AI/RPA solutions. Partner with IT leadership and the PMO to ensure disciplined execution.
• Represent TAG as an AI thought leader, and serve as the internal champion for a data-driven, AI-enabled culture.
• Frame complex choices for executive decision-making — synthesizing ambiguous information into clear options with well-reasoned recommendations.

Minimum Education and Experience

• 10+ years of progressive experience in strategy, transformation, technology, or analytics-intensive roles, with demonstrated career growth.
• Proven track record driving large-scale, cross-functional transformation programs — ideally including at least one major AI, data, or automation initiative.
• Experience working within or serving complex operating companies; comfort navigating matrixed, multi-stakeholder environments.
• Applied familiarity with AI/ML, data analytics platforms, and automation tools (e.g., RPA, GenAI, predictive modeling) — sufficient to evaluate vendors and partner with technical teams.
• Exceptional executive communication skills: ability to translate complex technology concepts into clear, business-focused narratives for C-suite and board-level audiences.
• Demonstrated ability to build and lead cross-functional teams; experience influencing without direct authority.
• Master's degree preferred (MBA, MS in Analytics, Computer Science, or related field).
• Experience in or exposure to healthcare, multi-unit consumer services, or similarly regulated industries preferred.

Backgrounds We Are Excited About

We will consider strong candidates from diverse backgrounds, including:

• Strategy or management consulting (MBB/Big 4) with a focus on digital, AI, or operations transformation — especially candidates who have moved into operating or in-house roles and demonstrated execution capability.
• Private equity or PE-backed operating environments, with experience in rapid value creation through technology and process improvement across portfolio companies.