Senior Project Manager, Enterprise AI Strategy – Execution

Trissential

. Partner with executive leaders to support development and execution of enterprise AI strategy .

Posted 11/11/2026full-timeMilwaukee • Wisconsin • United StatesSenior💰 $96 - $106 per hourWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in leading enterprise AI initiatives, including Microsoft Copilot implementation and Organizational Change Management. Proven ability to communicate complex technology concepts to executive stakeholders and drive technology adoption aligned with business objectives.

Highest-signal resume keywords

Enterprise AI InitiativesMicrosoft Copilot SolutionsOrganizational Change ManagementExecutive CommunicationProject Management Professional (PMP)

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

AI Adoption StrategiesBusiness Transformation ProgramsGovernance StructuresStrategic RoadmapsChange Readiness AssessmentsExecutive Reporting FrameworksPowerPoint ExpertiseStakeholder ManagementComplex Workstream ManagementBusiness Acumen

Soft Skills

Influencing SkillsNegotiation SkillsRelationship BuildingEmotional IntelligenceFacilitation Skills

Tools & Technologies

Microsoft AIAzure AIMicrosoft 365 Copilot

Certifications & Qualifications

Project Management Professional (PMP)Prosci Change Management CertificationAgile CertificationSAFe Certification

Industry Keywords

Enterprise Technology ImplementationsC-Suite StakeholdersChange ManagementStrategic Decision MakingTechnology Adoption

Tech Stack

Tools & technologies

AzurePMP

About the role

Key responsibilities & impact

Partner with executive leaders to support development and execution of enterprise AI strategy
Facilitate leadership discussions on priorities, investments, risks, and strategic decisions
Develop 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 by identifying challenges and solutions
Lead enterprise AI initiatives from planning through execution and adoption
Oversee Microsoft Copilot implementation, deployment, adoption, and value realization
Manage AI operations and maintenance activities
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
Evaluate and prioritize emerging AI opportunities aligned with business objectives
Integrate Organizational Change Management principles into AI programs
Develop change readiness assessments, communication plans, training strategies, and adoption programs
Drive technology adoption and workforce engagement
Identify organizational barriers, resistance points, and change risks
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 with diverse stakeholders
Communicate complex information concisely and persuasively
Handle sensitive organizational initiatives and discussions with discretion

Requirements

What you’ll need

10+ years of experience as a Senior Project Manager, Program Manager, Transformation Leader, or 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 within matrixed organizations
Strong Organizational Change Management (OCM), 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 with the 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
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
Must be authorized to work in the United States without sponsorship

Benefits

Comp & perks

Comprehensive medical plans
Dental insurance
Vision insurance
HSA with company contribution
Company-sponsored life insurance
Short-term disability insurance
Long-term disability insurance
Voluntary legal, hospital, accident, and pet wellness plans
401(k) with matching
Paid holidays
Paid time off
Career development and advancement opportunities
Strong team culture
Hybrid work arrangement