Head of AI

Advantive is hiring a Head of AI to lead AI strategy, operational transformation, and AI adoption across the company and its products, driving measurable productivity, operational, and business impact. Reporting directly to the CEO and working in close partnership with the SVP of Productivity, the CTO organization, and functional leaders across the business, this leader will drive the execution of Advantive’s AI strategy and help transform how the company operates, scales, and delivers value.

This is not a research role, an IT administration role, or a centralized innovation-lab role. This is a high-impact execution role for a business-minded operator who understands AI deeply enough to build with it, challenge existing ways of working, and drive lasting adoption across the organization.

• Lead enterprise-wide AI strategy and transformation initiatives across Advantive, driving measurable productivity, operational, and business impact.
• Partner with the CTO organization and business leaders to ensure AI is embedded in systems, workflows, and operations in a scalable and practical way.
• Rapidly prototype AI workflows, agents, and proof-of-concepts to validate business value and accelerate organizational adoption.
• Drive lasting organizational change through enablement, communication, training, and change management.
• Challenge existing workflows and operating models by identifying opportunities where AI can remove friction and accelerate execution.
• Act as an internal AI evangelist and trusted advisor, translating emerging AI capabilities into practical business applications.

What Success Looks Like: 

• AI becomes embedded into the day-to-day operating rhythm of the company, with strong adoption across functions and teams.
• Clear productivity, operational, and business impact tied to specific AI-enabled workflows and initiatives.
• AI becomes a practical and trusted capability across the organization — not a side initiative, but a core part of how we operate. 

The Ideal Candidate Profile

Background: A business-minded operator who has evolved into an AI-native leader through hands-on implementation, experimentation, and operational execution.

Experience: Proven experience implementing and operationalizing AI workflows, automations, agents, or transformation initiatives — not just advising on them.

Skills: Comfortable prototyping, experimenting with AI tooling, and rapidly iterating on workflows and operational improvements. Comfort reading and testing code is a plus, but driving adoption and execution is the core responsibility.

Mindset: Highly curious, learns fast, biased toward action, and obsessed with measurable outcomes, adoption, and execution rather than activity.

Change Leadership: Able to influence without authority and drive alignment across technical and non-technical stakeholders.

Execution: Comfortable rolling up sleeves, operating in ambiguity, and personally pushing initiatives across the finish line.

Location: Tampa, FL

In-office requirement: 2+ days a week

While we offer workplace flexibility, this role currently requires onsite presence two days per week at our Tampa office to support team alignment and cross-functional collaboration. Please note that in-office requirements are subject to change.

Advantive believes the companies that win over the next decade will be the ones that successfully operationalize AI, not just inside their products, but throughout the way they work. We are investing aggressively in AI across the company and creating a leadership role with the visibility, executive support, and organizational mandate needed to drive real transformation. If you are someone who builds, experiments, drives change, and pushes organizations to move faster and think differently — we want to talk.