Head of Automation & AI Strategy

Stream Companies•West Chester, PA

16h

About The Position

We are seeking a strategic, execution-oriented leader to help shape how our agency uses AI and automation to transform the way work gets done. The Head of Automation & AI Strategy will identify high-impact opportunities across the business, redesign workflows, drive adoption, and help scale practical AI-enabled solutions that improve efficiency, quality, and business performance. This leader will work cross-functionally to turn emerging ideas into repeatable capabilities that support our teams, clients, and long-term growth.

Requirements

5+ years of experience in automation, AI strategy, digital transformation, operations, workflow redesign, or a related leadership role in a complex business environment.
Strong understanding of digital marketing and media services, with working knowledge of key channels and workflows such as SEO, Paid Search, Paid Social, analytics, reporting, or related performance marketing functions.
Demonstrated ability to translate business needs into scalable process improvements, operating models, and technology-enabled solutions.
Experience leading cross-functional initiatives that require stakeholder alignment, change management, and adoption across multiple teams.
Experience working within project management and workflow systems such as ClickUp to support process design, execution, visibility, and cross-functional collaboration.
Proven success moving ideas from concept to execution, including pilots, rollout planning, training, and scaled implementation.
Technical fluency in AI, automation, systems integration, workflow platforms, and enterprise tools, with the ability to assess what is possible and guide implementation partners effectively.
Strong business and operational acumen, with the ability to connect new ways of working to measurable performance outcomes.
Experience creating documentation, training programs, playbooks, or enablement resources that help teams adopt new processes and technologies.
Excellent communication, facilitation, and influencing skills, with the ability to work effectively with senior leaders as well as frontline subject matter experts.
Comfort operating in fast-moving, ambiguous environments where the right structure, governance, and execution model still need to be built.

Responsibilities

Identify, prioritize, and lead high-impact AI and automation opportunities across the agency, with a focus on improving the way work is delivered across core digital services such as SEO, Paid Search, Paid Social, reporting, creative production, and client communication.
Partner with functional leaders and subject matter experts to understand how digital and media workflows operate today and where AI or automation can improve speed, consistency, quality, and scalability.
Redesign workflows with AI and automation embedded from the start, creating more efficient and resilient ways of working across teams.
Lead AI initiatives from concept through pilot, rollout, adoption, and scaled implementation, ensuring each effort has clear ownership, measurable outcomes, and a practical execution plan.
Define automation opportunities within project management and workflow systems, including how teams should use platform capabilities, embedded automations, and the platform’s AI functionality to improve execution, visibility, and coordination.
Define and track success metrics for major initiatives, including efficiency gains, time savings, output quality, adoption, and business impact.
Build strong cross-functional partnerships across operations, innovation, product, systems, data, and department leadership to align priorities and drive execution.
Help establish the agency’s operating model for AI, including roles, responsibilities, governance practices, and decision-making frameworks that support sustainable adoption.
Develop strategies for internal agents, automations, and connected workflows that reduce manual coordination and create repeatable operational advantage.
Work alongside Stream’s Learning & Development team to create and scale training programs, playbooks, and enablement resources that help teams confidently adopt new tools and processes.
Evaluate emerging technologies and AI opportunities through both a strategic and practical lens, balancing innovation, feasibility, user adoption, and business value.
Support quality assurance, governance, and responsible use practices so AI-enabled outputs meet internal standards and client expectations.
Serve as a visible leader and change agent who can influence stakeholders, navigate resistance, and build momentum around new ways of working.