GenAI & Enterprise Transformation Program Lead

Jobtailor; Chicago (IL); On-site; USD 120,000 - 170,000; Full time

Job summary

Jobtailor in Chicago seeks a Program Manager to lead strategic digital product initiatives, GenAI platforms, and enterprise transformations. You will coordinate cross-functional teams across functions and geographies, translating business goals into actionable roadmaps and delivery strategies.

The role requires strong experience in software lifecycle, agile practices, and governance, with a track record of influencing executives and delivering measurable value.

Qualifications

• Experience leading complex technology programs or digital transformations
• Experience delivering enterprise-scale software, cloud, data, AI, or digital product initiatives
• Proven ability to lead cross-functional teams in matrixed organizations
• Strong understanding of software development lifecycle, agile delivery, architecture principles, and platform ecosystems
• Experience with GenAI, advanced analytics, data platforms, or machine learning solutions
• Experience managing external system integrators and technology vendors
• Experience managing executive stakeholders and enterprise governance processes
• Excellent communication, facilitation, and influence skills

Responsibilities

• Assist with end-to-end delivery of strategically important digital products and transformation initiatives, GenAI solutions, platforms, and innovation programs
• Support complex enterprise programs spanning multiple business functions, geographies, and technology domains
• Translate business goals into executable technical roadmaps and delivery strategies
• Drive prioritization, sequencing, funding discussions, and value realization planning
• Support delivery planning from discovery through deployment and value realization
• Establish and manage program plans, milestones, dependencies, risks, assumptions, and resource requirements
• Partner with engineering and architecture teams to validate solution approaches and technical feasibility
• Lead technical design reviews and execution planning
• Ensure alignment with enterprise architecture, security, compliance, and operational requirements
• Build partnerships with executive sponsors, functional leaders, and technology teams
• Communicate program status, risks, decisions, and value delivery to senior leadership
• Manage program budgets, vendor engagements, and investment plans
• Establish KPIs, success criteria, and outcome measurement frameworks

Skills

GenAI

Enterprise-scale software

Cross-functional leadership

Software development lifecycle

Agile delivery

Platform ecosystems

Vendor management

Executive stakeholder management

Communication & influence

Tools

Cloud Platforms

Advanced Analytics Tools

Vendor Management Systems

Job description

Jobtailor in Chicago seeks a Program Manager to lead strategic digital product initiatives, GenAI platforms, and enterprise transformations. You will coordinate cross-functional teams across functions and geographies, translating business goals into actionable roadmaps and delivery strategies.

The role requires strong experience in software lifecycle, agile practices, and governance, with a track record of influencing executives and delivering measurable value.