Senior AI Strategy & Transformation Director

The Washington Post; Washington (District of Columbia); On-site; USD 233,000 - 388,000; Full time

Benefits offered by this job

Medical, dental, vision

401(k) with match

Paid vacation and sick leave

Paid holidays

Parental leave

Mental health resources

Free Post digital subscription

Job summary

The Washington Post is pursuing a Senior Director, Artificial Intelligence Strategy & Transformation to shape enterprise AI strategy and governance across Editorial, Product, Technology, and business functions. You will translate rapid AI advances into practical strategies that strengthen journalism, accelerate product innovation, and improve customer experiences.

You will build an enterprise AI roadmap, establish an AI Center of Excellence, and drive responsible deployment at scale with

Qualifications

• Significant senior leadership experience delivering AI, technology, digital transformation, product, data, or innovation strategies within large or complex organizations.
• Proven success leading cross-functional transformation initiatives with measurable outcomes.
• Deep knowledge of AI, Generative AI, ML, LLMs and intelligent automation.
• Understanding deploying AI at scale: architecture, data quality, security, scalability, cost.
• Experience evaluating build‑versus‑buy and working with internal and external platforms.
• Experience developing responsible AI governance, evaluation frameworks, and model‑risk controls.
• Ability to translate complex technical concepts into clear business strategies and investment priorities.
• Strong financial acumen, ROI measurement and business case development.
• Ability to influence senior executives and cross‑functional leaders.
• Proven leadership of multidisciplinary teams and complex initiatives.

Responsibilities

• Develop the enterprise AI strategy and multi‑year roadmap in partnership with executive leadership.
• Lead execution of the enterprise AI roadmap with milestones, governance, and performance measures.
• Identify and evaluate high‑value AI opportunities across journalism, product, advertising, and operations.
• Develop business cases and ROI analyses for AI initiatives with cost, feasibility, and impact assessments.
• Coordinate the enterprise AI portfolio with functional leads to ensure alignment and accountability.
• Lead cross‑functional AI initiatives to improve productivity, decision‑making, and customer experiences.
• Establish an enterprise AI Center of Excellence with reusable frameworks and resources.
• Develop governance frameworks for responsible AI in partnership with Legal, Security, Privacy and others.
• Evaluate AI models, platforms, and partners; advise build vs buy decisions and scalability considerations.
• Translate emerging AI capabilities into scalable products and customer experiences alongside Product and Tech.
• Provide strategic advisory to leadership, translating trends into actionable recommendations.
• Support executive and Board discussions with strategic analyses and investment cases.
• Build AI capability through education, change management, and communities of practice.
• Establish performance measures tracking adoption, impact, and governance maturity.
• Monitor emerging AI tech and market developments and assess implications for the company.
• Represent The Washington Post in industry forums as an AI subject‑matter expert.

Skills

AI strategy

Cross-functional leadership

Digital transformation

Executive communication

Change management

Governance

Strategic advising

ROI & budget

Influence senior leaders

Complex programs

Education

Bachelor's degree

Advanced degree preferred

Job description

The Washington Post is pursuing a Senior Director, Artificial Intelligence Strategy & Transformation to shape enterprise AI strategy and governance across Editorial, Product, Technology, and business functions. You will translate rapid AI advances into practical strategies that strengthen journalism, accelerate product innovation, and improve customer experiences.

You will build an enterprise AI roadmap, establish an AI Center of Excellence, and drive responsible deployment at scale with