Remote AI Program Leader - Enterprise Delivery

CAI; Helena (MT); Remote; USD 110,000 - 124,000; Full time

Benefits offered by this job

Medical, dental, and vision insurance

401k retirement plan

Paid time off

Job summary

CAI is seeking an AI Program Manager to lead and oversee a portfolio of enterprise AI initiatives, driving cross-functional execution and ensuring delivery of business outcomes. This contract, remote role requires work authorization without sponsorship.

You will manage end-to-end delivery with executive reporting, governance, and stakeholder alignment across data science, engineering, IT, security, and compliance teams.

Qualifications

• Bachelor’s degree in Engineering, CS, Business Administration, or 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 with 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 AI programs, ensuring alignment with objectives, timelines, budgets, and quality.
• Partner with executive leadership to identify risks, drive critical decisions, remove obstacles, and maintain accountability.
• 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 elevate infrastructure, platform, security, and operational roadblocks through resolution.

Skills

Portfolio management

Budgeting

AI/ML concepts

Data pipelines

Stakeholder management

Executive presentation

Agile methodologies

Cloud basics

Problem solving

Drive accountability

Education

Bachelor’s degree in Engineering / CS / Business Administration

Tools

Planisware

JIRA

Microsoft Project

Asana

Smartsheet

Job description

CAI is seeking an AI Program Manager to lead and oversee a portfolio of enterprise AI initiatives, driving cross-functional execution and ensuring delivery of business outcomes. This contract, remote role requires work authorization without sponsorship.

You will manage end-to-end delivery with executive reporting, governance, and stakeholder alignment across data science, engineering, IT, security, and compliance teams.