AI Program Delivery Lead

IT Program Delivery Lead
Brooksource
Fortune 50 Health Insurance Client
Position Overview
The Program Delivery Lead will play a highly visible role within the Enterprise AI organization, supporting the delivery and operational execution of strategic AI products, reusable platform capabilities, and cross-functional technology initiatives. This role serves as a strategic delivery leader and trusted consultant, partnering closely with Enterprise AI leadership, Product Management, Engineering, and business stakeholders to drive execution, establish governance, manage dependencies, and ensure alignment to business objectives.
The ideal candidate brings a strong consulting and digital transformation background, with the ability to operate effectively in ambiguous and evolving environments. This person will be comfortable engaging with senior leaders, challenging assumptions, identifying gaps, facilitating decisions, and elevating conversations beyond the project plan to help stakeholders make informed decisions and drive outcomes.
The Enterprise AI organization is supporting approximately nine strategic products, with individual Program Delivery Leads typically supporting two to three initiatives at a time. These are highly visible assignments with significant exposure to Directors, VPs, and other senior stakeholders.
Key Responsibilities

• Lead complex, cross-functional programs and strategic initiatives from planning through execution and delivery.
• Partner directly with Enterprise AI leadership and Directors to establish delivery strategies, operating models, governance structures, and execution rhythms.
• Serve as a trusted advisor to stakeholders, bringing strategic perspective and helping teams navigate complex or ambiguous challenges.
• Drive alignment across Product, Engineering, Technology, Operations, and business stakeholders.
• Establish and maintain program governance, accountability models, operating cadences, and executive reporting.
• Identify and proactively manage risks, dependencies, organizational barriers, and cross-functional challenges.
• Facilitate executive-level discussions, decision-making, and alignment across competing priorities.
• Translate complex business and technical concepts into clear, actionable plans and communications.
• Elevate issues and opportunities beyond the project level to identify broader organizational impacts and solutions.
• Coordinate multiple workstreams and ensure delivery remains aligned to business objectives and expected outcomes.
• Challenge assumptions, identify gaps, and bring structure and clarity to evolving initiatives.
• Support the development and evolution of Enterprise AI delivery practices, processes, and operating models.
• Partner with Product and Engineering leadership to ensure effective execution of enterprise AI products and capabilities.
• Communicate program status, risks, decisions, and strategic considerations to Director- and VP-level audiences.

Required Qualifications

• 8+ years of experience in program delivery, technology transformation, consulting, PMO leadership, or strategic delivery within complex organizations.
• Experience supporting AI, artificial intelligence, advanced analytics, data, automation, or emerging technology initiatives.
• Demonstrated aptitude for AI and familiarity with AI-enabled products, machine learning concepts, data-driven solutions, or modern technology delivery practices.
• Experience working within product-centric and Agile delivery environments.
• Experience supporting shared platforms, enterprise capabilities, or reusable technology services.
• Familiarity with modern cloud, data, analytics, and AI ecosystems.
• Experience within healthcare, payer, or other highly regulated industries.
• Experience using AI-enabled productivity and delivery acceleration tools.
• Experience working in large, complex enterprise environments.
• 5+ years of consulting experience, ideally supporting digital transformation, technology modernization, enterprise transformation, or operating model initiatives.
• Proven experience leading complex, cross-functional initiatives through influence, governance, collaboration, and stakeholder alignment.
• Strong experience partnering with senior business and technology leaders, including Director- and VP-level stakeholders.
• Demonstrated ability to operate effectively in ambiguous environments and bring structure, clarity, and accountability to complex initiatives.
• Strong strategic thinking and the ability to understand the broader business context beyond the project plan.
• Exceptional communication, facilitation, negotiation, and stakeholder management skills.
• Ability to translate effectively between business, product, engineering, and operational teams.
• Experience establishing governance frameworks, operating rhythms, accountability models, and execution processes.
• Experience leading large-scale technology, digital, data, AI, platform, product, or business transformation initiatives.
• Bachelor's degree or equivalent experience.
• PMP, PgMP, SAFe, or comparable program/project management certification preferred.

Ideal Candidate Profile
The ideal candidate is a consultant at heart who knows how to drive delivery. They are strategic, collaborative, and comfortable operating at the intersection of business and technology. They do not need to be the person solving the technical problem. Instead, they excel at bringing the right people together, asking the right questions, identifying gaps, creating alignment, and moving complex initiatives forward.
This person is comfortable interacting with senior leadership and can move seamlessly between strategic conversations with VPs and detailed execution discussions with Product and Engineering teams. They are proactive, confident, highly collaborative, and able to influence outcomes without relying solely on formal authority.
A strong background in digital transformation consulting, coupled with formal program/project management experience such as a PMP, will be highly valuable.