Senior Project Manager, Enterprise AI Strategy & Execution

Expleo•Milwaukee, WI

14h•$96 - $106•Hybrid

About The Position

Trissential is seeking a Senior Project Manager to help a client shape and execute enterprise AI strategy and transformation initiatives. This strategic leadership role partners directly with executive leadership and spans executive strategy, organizational change, AI innovation, and business transformation. The position is hybrid in Milwaukee, Wisconsin, with three or fewer days per week in the office, and is full-time. The role leads enterprise AI initiatives from planning through execution and adoption, including Microsoft Copilot implementation, AI operations, and emerging AI opportunities. It establishes governance, milestones, risk management, and executive reporting while coordinating cross-functional workstreams and tracking dependencies, resources, timelines, and priorities. It also integrates organizational change management into AI programs by supporting readiness, communications, training, adoption, workforce engagement, and measurement of business value. The Senior Project Manager serves as a trusted advisor to executive stakeholders, facilitating alignment on priorities, investments, risks, and decisions. The role prepares executive briefings, strategic roadmaps, board-ready presentations, and leadership updates, translating complex AI and technology concepts into clear business recommendations. The successful candidate will help drive responsible AI adoption and measurable business outcomes in a large, complex organization. Candidates must be authorized to work in the United States without sponsorship. Compensation is $96–$106 per hour, with final compensation based on skills, experience, and geography.

Requirements

10+ years of experience as a Senior Project Manager, Program Manager, Transformation Leader, or in a related strategic leadership role.
Proven experience partnering directly with executive leadership and C-suite stakeholders.
Strong understanding of enterprise AI initiatives, Generative AI, AI adoption strategies, and Microsoft Copilot solutions.
Experience leading large-scale enterprise technology implementations and business transformation programs.
Demonstrated success managing multiple complex workstreams in matrixed organizations.
Strong organizational change management, change-readiness, and adoption experience.
Exceptional executive communication, facilitation, and stakeholder management skills.
Advanced PowerPoint and executive presentation development expertise.
Ability to influence, negotiate, and build consensus without direct authority.
Experience establishing governance structures, strategic roadmaps, and executive reporting frameworks.
Strong business acumen and ability to connect technology initiatives to business outcomes.
Ability to thrive in ambiguity while anticipating organizational needs and challenges.
High emotional intelligence, political savvy, and relationship-building skills.
Bachelor's degree in Business, Information Technology, Computer Science, Organizational Development, Project Management, or a related field.
Authorization to work in the United States without sponsorship.

Nice To Haves

Experience supporting enterprise AI strategy programs and AI transformation initiatives.
Hands-on involvement with Microsoft 365 Copilot implementations and enterprise adoption efforts.
Knowledge of AI governance, responsible AI frameworks, and AI operating models.
Experience supporting executive steering committees and transformation leadership boards.
Background working within large, complex, regulated organizations.
Experience in utilities, energy, or highly regulated industries.
Familiarity with AI operations, AI service management, and long-term AI support models.
Certifications related to Organizational Change Management, Program Management, Agile, or AI technologies.
Project Management Professional (PMP) certification preferred.
Prosci Change Management Certification preferred.
Agile, SAFe, or related project/program management certifications are a plus.
Microsoft AI, Azure AI, or Microsoft 365 Copilot certifications are highly desirable.

Responsibilities

Partner with executive leaders to develop and execute enterprise AI strategy.
Facilitate leadership discussions to align stakeholders on priorities, investments, risks, and strategic decisions.
Prepare executive briefings, strategic roadmaps, board-ready presentations, and decision-making materials.
Translate complex AI, Microsoft Copilot, and technology concepts into clear business recommendations.
Advise executive stakeholders and proactively identify challenges and solutions.
Lead enterprise AI initiatives from planning through execution and adoption.
Oversee Microsoft Copilot implementation, deployment, adoption, and value-realization efforts.
Manage AI operations and maintenance activities to support long-term program success.
Coordinate cross-functional workstreams involving business leaders, technical teams, and vendors.
Establish project governance, milestones, risk management processes, and executive reporting frameworks.
Track dependencies, resources, timelines, and competing priorities across strategic initiatives.
Evaluate and prioritize emerging AI opportunities aligned with business objectives.
Integrate organizational change management principles into AI programs and strategic initiatives.
Develop change-readiness assessments, communication plans, training strategies, and adoption programs.
Partner with stakeholders to support technology adoption and workforce engagement.
Identify organizational barriers, resistance points, and change risks.
Support responsible AI adoption through communication and stakeholder engagement.
Measure and report adoption outcomes and business value realization.
Build relationships with executive leaders, business partners, and technology teams.
Develop executive presentations, communications, and leadership updates; facilitate meetings and workshops; and communicate complex information clearly and persuasively.
Use discretion when handling sensitive organizational initiatives and discussions.