Senior Director, Artificial Intelligence

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

Join the future of news We’re on a mission to deliver riveting storytelling for all of America. At The Washington Post, you’ll help reinvent news. Our work is driven by a deep investigative spirit and enhanced by innovation to bring audiences closer to the stories that matter most.

About Our Team

About Our Team The Washington Post is powered by the passion and talent of our people. It takes all of us to reinvent news. Beyond our award-winning News and Opinions teams, we work across many departments, including Brand & Events, Communications, Customer Care, Engineering & Product, Finance, Human Resources, Legal, Marketing & Advertising, Print Operations, and Sales.

Why This Role Matters

Artificial Intelligence is reshaping how news organizations create products, serve audiences, operate their businesses, and compete. The Washington Post is seeking a Senior Director, Artificial Intelligence Strategy & Transformation to help define and execute how AI is responsibly applied across the enterprise. This role leads the development and execution of the company’s enterprise AI strategy in partnership with executive, editorial, product, technology, commercial, and corporate leaders. The Senior Director translates rapidly evolving AI capabilities into practical opportunities that strengthen journalism, accelerate product innovation, improve customer experiences, increase organizational effectiveness, and create measurable business value.

Serving as a senior enterprise subject-matter leader for AI strategy and responsible adoption, this role develops recommendations for the enterprise AI roadmap, coordinates priorities across functions, and leads cross-functional initiatives that convert AI investments into measurable outcomes. The role will help establish the standards, governance practices, evaluation frameworks, and operating models that enable teams across The Washington Post to adopt AI responsibly and at scale. The Senior Director will also help determine where the company should build, buy, partner, or experiment, balancing technical capability, cost, scalability, data rights, security, accuracy, editorial integrity, and long‑term strategic value.

What Motivates You

You are energized by the opportunity to help shape how AI transforms journalism, products, customer experiences, and business operations. You enjoy translating emerging technologies into practical strategies and measurable business outcomes. You thrive in complex environments where success depends on influence, collaboration, and alignment across multiple functions. You are passionate about responsible AI and believe innovation should strengthen trust, accuracy, transparency, and organizational integrity. You are comfortable operating between technical teams and business leaders and can translate complex technical concepts into clear strategic choices. You enjoy developing frameworks, standards, and operating models that help organizations adopt new technologies consistently and responsibly. You are motivated by identifying high‑value use cases and moving them from concept through evaluation, implementation, and measurable impact. You value experimentation, but you also bring discipline to investment decisions, governance, risk management, and performance measurement. You enjoy building organizational capability by increasing AI literacy, strengthening cross‑functional collaboration, and helping teams adopt new tools effectively. You are comfortable working in areas where technology, business strategy, ethics, editorial standards, and regulation intersect.

How You'll Support the Mission

Develop and recommend the enterprise AI strategy and multi‑year roadmap in partnership with executive and functional leadership, translating organizational priorities into a coordinated portfolio of AI initiatives.

Lead execution of the approved enterprise AI roadmap, establishing milestones, priorities, dependencies, governance practices, and performance measures that support measurable business outcomes.

Identify and evaluate high‑value AI opportunities across journalism, product development, advertising, subscriptions, customer experience, finance, HR, legal, and corporate operations.

Develop business cases and investment recommendations for AI initiatives, including expected business impact, cost, scalability, technical feasibility, implementation risk, and return on investment.

Coordinate the enterprise AI portfolio, working with functional leaders who retain accountability for their respective products, operations, budgets, and business outcomes.

Lead cross‑functional AI initiatives that improve productivity, decision‑making, customer experiences, digital capabilities, commercial performance, and organizational effectiveness.

Establish and operate an enterprise AI Center of Excellence or similar capability, providing reusable frameworks, technical guidance, evaluation practices, governance support, education, and implementation resources across the company.

Develop responsible AI governance frameworks and operating standards in partnership with Legal, Editorial Standards, Information Security, Privacy, Technology, Product, and other governance functions.

Create evaluation and quality frameworks for AI solutions, including standards for accuracy, reliability, bias, transparency, security, data use, and responsible deployment.

Evaluate AI models, platforms, tools, and technology partners, providing recommendations regarding build‑versus‑buy decisions, third‑party solutions, proprietary capabilities, scalability, latency, cost, data rights, and long‑term strategic value.

Partner with Product and Technology leaders to help translate emerging AI capabilities into scalable products, platforms, and customer experiences.

Serve as a senior strategic advisor and subject‑matter expert to leadership, translating technical developments, market trends, and emerging AI capabilities into business implications, opportunities, risks, and actionable recommendations.

Support executive and Board discussions regarding AI by preparing strategic analysis, recommendations, risk assessments, market intelligence, investment cases, and progress reporting as requested by executive leadership.

Build organizational AI capability and fluency through executive education, employee enablement, change management, communities of practice, and collaboration with functional leaders.

Establish enterprise AI performance measures that track adoption, business impact, productivity, financial outcomes, quality, responsible‑use standards, and organizational maturity.

Monitor emerging AI technologies and market developments and assess their potential implications for journalism, media, advertising, subscriptions, technology, and The Washington Post’s competitive position.

Represent The Washington Post in selected industry, academic, technology, and professional forums as an AI subject‑matter expert in coordination with executive leadership and Communications.

The Skills and Experience You Bring

• Significant senior leadership experience developing and executing AI, technology, digital transformation, product, data, or innovation strategies within large or complex organizations.
• Demonstrated success leading complex, cross‑functional transformation initiatives that delivered measurable business, financial, customer, or operational outcomes.
• Strong knowledge of Artificial Intelligence, Generative AI, Machine Learning, Large Language Models, retrieval‑based systems, intelligent automation, predictive analytics, and emerging AI technologies.
• Strong understanding of the practical considerations involved in deploying AI at scale, including architecture, model selection, evaluation, data quality, integration, security, scalability, latency, and cost.
• Experience evaluating build‑versus‑buy decisions and working with both internally developed capabilities and third‑party AI platforms or foundation models.
• Experience developing or implementing responsible AI governance, evaluation frameworks, model‑risk practices, privacy controls, security standards, or related operating models.
• Demonstrated ability to translate complex technical concepts and emerging technology trends into clear business strategies, investment recommendations, and implementation priorities.
• Strong financial and business acumen, including experience developing business cases, evaluating technology investments, measuring ROI, and assessing business impact.
• Demonstrated ability to influence senior executives and cross‑functional leaders in environments where authority is distributed across multiple functions.
• Experience leading multidisciplinary teams and complex initiatives through both direct management and influence.
• Strong change‑management capability and experience driving adoption of new technologies, operating models, or ways of working across an organization.
• Excellent communication and presentation skills, with the ability to engage technical teams, business leaders, editorial stakeholders, and executive audiences.
• Strong judgment and comfort operating in areas involving ambiguity, emerging technology, organizational risk, and competing business priorities.
• Experience in media, publishing, digital content, consumer technology, information services, or another environment where accuracy, trust, and customer experience are critical is preferred.
• Bachelor’s degree in Computer Science, Artificial Intelligence, Engineering, Data Science, Information Systems, Business, or a related field, or equivalent professional experience.
• An advanced degree is preferred but not required.
• Active engagement in the AI ecosystem through industry organizations, research, conferences, standards bodies, or professional communities is preferred.

Leadership Scope

This role leads a specialized enterprise AI capability and may manage a combination of AI strategy, product, technical, program, governance, and transformation professionals. The Senior Director leads broadly through influence across Editorial, Product, Technology, Revenue, Finance, Legal, Human Resources, Security, Privacy, and other functions. The role is accountable for the quality and execution of the enterprise AI strategy, roadmap process, governance frameworks, and cross‑functional AI programs, but does not replace the accountability of functional executives for their respective organizations, products, budgets, or business outcomes. Major enterprise AI investments, policies, portfolio priorities, and strategic decisions remain subject to the appropriate executive and governance approval processes.

Collaboration makes us stronger. That’s why our offices are designed with open layouts, modern technology, and easy access to transportation. With certain exceptions for newsgathering and business travel, we work on‑site five days a week.

Compensation and Benefits

• Competitive medical, dental and vision coverage
• Company-paid pension and 401(k) match
• Three weeks of vacation and up to three weeks of paid sick leave
• Nine paid holidays and two personal days
• 20 weeks paid parental leave for any new parent
• Robust mental health resources
• Backup care and caregiver concierge services
• Gender affirming services
• Pet insurance
• Free Post digital subscription
• Leadership and career development programs
• Benefits may vary based on the job, full-time or part-time schedule, location, and collectively bargained status.

The salary range for this position is: $232,875 - $388,125 Annual The actual salary within this range will depend on individual skills, experience, and qualifications as they relate to specific job requirements.

This position may be eligible for a bonus or incentive program, and a member of the Talent Acquisition team will discuss bonus payment terms and conditions during the interview process.