Remote AI Program Lead for Enterprise Initiatives

CAI; Annapolis (MD); Remote; USD 110,000 - 124,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

401k retirement plan

Job summary

CAI is seeking an AI Program Manager to lead a portfolio of enterprise AI initiatives, driving cross‑functional execution, governance, and timely delivery of business outcomes. The role is contract and remote, with a strong emphasis on risk management and executive reporting.

Qualified candidates will have deep PM experience, proficiency with Jira and Planisware, and a background in AI/ML concepts, data pipelines, and deployment considerations. Work authorization required.

Qualifications

• Bachelor’s degree in Engineering, Computer Science, Business Administration, or a related field.
• 12+ years of program or project management experience in technology, data, digital transformation, or related environments.
• Experience leading large‑scale, cross‑functional programs involving multiple stakeholders and competing priorities.
• Demonstrated ability to engage, influence, and challenge senior leaders and executives.
• Working knowledge of AI/ML concepts, data pipelines, and deployment considerations.
• Experience using program and portfolio management tools such as Jira, Microsoft Project, Asana, or Smartsheet.
• Familiarity with Agile methodologies and software development lifecycle practices.
• Basic understanding of cloud platforms and IT infrastructure concepts.
• Strong stakeholder management, communication, and executive presentation skills.
• Proven problem‑solving, decision‑making, and organizational skills.
• Ability to thrive in fast‑paced, ambiguous environments and drive accountability without direct authority.

Responsibilities

• Lead end-to-end delivery of complex, interdependent AI programs, ensuring alignment with business objectives, timelines, budgets, and quality expectations.
• Partner with executive leadership to identify risks, drive critical decisions, remove obstacles, and maintain accountability across stakeholders.
• Provide program‑level reporting on status, risks, dependencies, and value realization to senior leadership.
• Coordinate efforts across data scientists, engineers, business stakeholders, IT operations, security teams, and compliance partners.
• Facilitate program kickoffs, steering committee meetings, and post‑implementation reviews.
• Assess incoming AI initiatives for feasibility, readiness, business value, and resource requirements.
• Support portfolio prioritization activities by evaluating impact, complexity, risk, and organizational capacity.
• Challenge scope, assumptions, and business cases to ensure realistic plans and measurable success criteria.
• Establish governance frameworks, delivery methodologies, and operational processes that balance innovation, speed, compliance, and quality.
• Serve as a liaison between AI and technology organizations to resolve technical and operational issues and improve service delivery.
• Track and escalates infrastructure, platform, security, and operational roadblocks through resolution.

Skills

Program management

Cross-functional leadership

Budgeting

Executive communication

Stakeholder management

Agile methodologies

Cloud concepts

Problem solving

Delivery governance

Education

Bachelor’s degree in Engineering, Computer Science, Business Administration, or related field

Tools

Jira

Planisware

Microsoft Project

Asana

Smartsheet

Job description

CAI is seeking an AI Program Manager to lead a portfolio of enterprise AI initiatives, driving cross‑functional execution, governance, and timely delivery of business outcomes. The role is contract and remote, with a strong emphasis on risk management and executive reporting.

Qualified candidates will have deep PM experience, proficiency with Jira and Planisware, and a background in AI/ML concepts, data pipelines, and deployment considerations. Work authorization required.