Transformation Program Manager

Our client,
the global leader in technology-enabled claims and risk management solutions, is actively looking for a Transformation Program Manager for an AI-enabled software delivery transformation focused on applying AI to software delivery practices. This role is 100% remote but candidates must be able to work CST!

*** This is a 12 month contract with the opportunity to extend based on performance and business needs***

This initiative will use a phased pilot-team approach to evaluate how AI can improve productivity, reduce manual effort, and create measurable cost savings. This Program Manager will work with business, technology, engineering, offshore teams, vendors, internal AI leadership, and senior stakeholders to shape and execute the AI-enabled delivery model. This role requires a hands-on program leader who can operate in ambiguity, create structure where the path is still being defined, drive decisions, remove obstacles, and keep the initiative moving toward measurable outcomes.

• Lead planning and delivery for the AI-enabled software delivery transformation, including work streams where the process, operating model, or implementation path is still evolving.
• Drive day-to-day execution across pilot teams, stakeholders, vendors, and offshore engineering partners.
• Work with leadership to select the most suitable projects and pilot teams for applying the AI-enabled delivery model.
• Build and manage the integrated project plan, including training, pilot execution, testing, adoption, measurement, and reporting.
• Clarify ownership, frame options and tradeoffs, drive decisions, and escalated issues when needed.
• Track milestones, dependencies, risks, issues, decisions, and action items through resolution.
• Help turn the AI-enabled delivery approach into practical guidance, documentation, and repeatable ways of working.
• Provide clear status updates, risks, issues, and recommendations to senior leadership.
• Support benefit tracking for productivity improvements, cost savings, resource usage, and AI-related consumption costs.

• 8+ years as a Technical Project Manager leading software development, IT transformation, or enterprise technology initiatives.
• 5+ years managing SDLC-based projects, including planning, development, testing, implementation, and adoption.
• 5+ years leading cross-functional enterprise delivery across business, technical, vendor, and offshore teams.
• 3+ years supporting transformation initiatives, pilot programs, phased rollouts, or process implementations.
• Proven ability to lead ambiguous or first-time initiatives where requirements, processes, stakeholders, or implementation approaches are still evolving.
• Strong project planning, coordination, risk management, and executive-level reporting skills.
• Ability to translate strategic goals into actionable plans and drive execution across multiple stakeholders.
• Strong communication skills with technical teams, business stakeholders, vendors, and leadership.

• Background in AI, automation, developer productivity tools, or AI-enabled software delivery.
• Familiarity with SDLC, Dev Ops, Agile, or technology operating model transformation.
• Demonstrated success measuring productivity gains, cost savings, resource efficiency, or business benefits tied to technology initiatives.
• Exposure to portfolio management, project financials, budget planning, or vendor strategy.
• Strong experience with Smartsheet and other PM tools.