Senior Project Manager, Enterprise AI Strategy & Execution

Overview

Location: Hybrid (Milwaukee, WI - 3 days per week or fewer in office)Employment Type: Full-Time

Are you passionate about shaping the future of AI within a large enterprise while partnering directly with executive leadership? Trissential is seeking an accomplished Senior Project Manager, Enterprise AI Strategy & Execution to join our client's team and play a critical role in driving enterprise AI transformation initiatives. This is far more than a traditional project management role. You'll sit at the intersection of executive strategy, organizational change, AI innovation, and business transformation, helping leaders navigate one of the most significant technology shifts of our time.

What's in It for You?

• Work directly with executive leadership on enterprise-wide AI strategy and transformation initiatives
• Influence high-impact decisions that shape the future direction of AI adoption across the organization
• Lead strategic initiatives including Microsoft Copilot rollout, AI operations, and emerging AI opportunities
• Partner with senior stakeholders across business and technology functions to drive measurable business outcomes
• Gain exposure to enterprise AI strategy, governance, responsible AI practices, and organizational transformation
• Play a key role in helping a highly respected utility organization navigate digital transformation and workforce change
• Leverage your executive communication skills while building trusted relationships throughout the organization
• Join a collaborative environment that values innovation, strategic thinking, and continuous improvement

Your Role & Responsibilities

Executive Leadership & Strategic Advisory

• Partner closely with executive leaders to support the development and execution of enterprise AI strategy
• Facilitate leadership discussions to align stakeholders 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
• Serve as a trusted advisor to executive stakeholders by proactively identifying challenges and solutions
• Navigate organizational dynamics with diplomacy, executive presence, and sound business judgment

Enterprise AI Program & Project Management

• 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 while ensuring long-term program success
• Coordinate multiple 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 that align with business objectives

Organizational Change Management & Adoption

• Integrate Organizational Change Management (OCM) principles into AI programs and strategic initiatives
• Develop change readiness assessments, communication plans, training strategies, and adoption programs
• Partner with stakeholders to drive successful technology adoption and workforce engagement
• Identify organizational barriers, resistance points, and change risks before they impact success
• Support responsible AI adoption through effective communication and stakeholder engagement
• Measure and report on adoption outcomes and business value realization

Executive Communications & Stakeholder Engagement

• Build strong relationships with executive leaders, business partners, and technology teams• Develop polished executive presentations, communications, and leadership updates• Facilitate meetings and workshops with diverse stakeholders and competing priorities• Communicate complex information in a concise, persuasive, and executive-friendly manner• Exercise discretion when handling sensitive organizational initiatives and discussions

Skills & Experience You Should Possess

• 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

Bonus Points If You Have

• 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 within 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

Education & Certifications You Need

• 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

What We Offer

At Trissential, we believe great talent thrives when empowered to make a meaningful impact. By joining our client's team, you'll help shape enterprise AI strategy while collaborating with executive leaders on transformative initiatives that drive lasting business value.

• Competitive Compensation - $96-$106 per hour. Final compensation is determined based on skill alignment, years of experience, and fair, market-based rates by geography.
• Comprehensive Benefits for you and your dependents - Extensive Medical Plans, Dental, Vision, HSA with company contribution, company sponsored Life Insurance and Short / Long term disability insurance, a host of voluntary plans including legal, hospital, accident, pet wellness, and 401k with matching
• Paid Holidays and Paid Time Off
• Career Development and Advancement - Expleo is a global company in 29 Countries worldwide with a high focus on development
• Strong Team Culture - Collaborate with experienced professionals who value precision, performance, and teamwork

Please note: This position is only open to candidates who are authorized to work in the United States without sponsorship.

Ready to be part of something exciting?

If you're a strategic leader who combines executive presence, organizational change expertise, AI transformation knowledge, and exceptional project management capabilities, we'd love to hear from you. Apply today and help lead the next generation of enterprise AI innovation while making a lasting impact on a major organization's digital transformation journey.