Program Manager - POS Transformation

Location: Fully Remote (Chicago, IL Preferred) Employment Type: Full-Time Are you an experienced Program Manager who thrives on leading complex enterprise transformations and driving meaningful business outcomes? Trissential is seeking a Program Manager - POS Transformation to join our client's team and lead a high-visibility Point-of-Sale modernization initiative. This is an opportunity to take ownership of a strategic transformation program, establish governance frameworks, drive pilot deployment success, and introduce AI-enabled program management practices that elevate delivery performance across the organization. If you're energized by solving complex challenges, influencing stakeholders, and building scalable delivery processes that leave a lasting impact, we'd love to connect with you. What's in It for You? Lead a strategic enterprise-wide POS transformation initiative with executive-level visibility and influence Shape governance frameworks, PMO processes, delivery methodologies, and deployment strategies that will be leveraged throughout the organization Drive a high-profile pilot implementation and influence future rollout decisions across multiple locations Collaborate with senior business leaders, technology teams, operations stakeholders, and third-party vendors Utilize Microsoft Copilot and AI-powered program management capabilities to improve execution, reporting, planning, and decision-making Take ownership of a large-scale modernization effort that directly impacts business performance and customer experience Join a collaborative, innovative, and results-oriented culture that values accountability and continuous improvement Work remotely while partnering with diverse teams across business and technology functions Your Role & Responsibilities Program Mobilization & PMO Establishment Assess the current state of the POS transformation program, including project scope, schedules, stakeholders, vendors, dependencies, risks, and delivery health Establish a practical and sustainable program management framework within the first several weeks of engagement Develop and maintain integrated program plans across multiple workstreams and stakeholder groups Design governance structures, escalation pathways, decision-making processes, and reporting frameworks Implement executive dashboards, KPIs, status reporting, and performance-tracking mechanisms Create sustainable program management processes and tools that support long-term organizational success Establish clear ownership, accountability, and execution alignment across internal teams and vendor partners POS Pilot Planning & Execution Lead planning and execution activities required to achieve pilot deployment readiness Manage integrated schedules across technology, testing, operations, implementation, and vendor workstreams Coordinate store readiness activities, deployment preparation, launch support, and post-launch stabilization efforts Identify critical path items, delivery risks, dependencies, and mitigation strategies Facilitate milestone reviews, readiness assessments, and go/no-go decision processes Drive issue resolution and escalation management to keep delivery objectives on track Capture lessons learned and establish repeatable deployment processes for future rollouts AI-Enabled Program Management Leverage AI-powered tools to improve planning, scheduling, reporting, documentation, and execution activities Analyze program data to identify emerging risks, dependency challenges, and mitigation opportunities Create executive communications, status reports, dashboards, and updates through efficient AI-assisted workflows Improve knowledge management, documentation quality, and information accessibility across the program Enhance meeting preparation, action tracking, and follow-up management practices Identify opportunities to reduce administrative workload through practical AI-enabled process improvements Validate all AI-generated outputs against authoritative program information before executive distribution or decision-making Vendor & Stakeholder Leadership Serve as the primary coordination point between leadership teams, business partners, technology groups, and external vendors Drive accountability for program milestones, deliverables, and execution commitments Effectively communicate complex technical concepts to non-technical stakeholders Identify delivery challenges early and recommend practical solutions Deliver transparent executive-level reporting regarding program health, progress, risks, decisions, and key milestones Influence teams and drive alignment without relying on direct reporting authority Tools, Governance & Continuous Improvement Utilize Microsoft Teams, SharePoint, Planner, Microsoft Copilot, and related collaboration technologies Develop repeatable governance practices, reporting frameworks, templates, and deployment artifacts Ensure AI-enabled delivery processes align with security, confidentiality, and organizational policy requirements Support knowledge transfer and long-term sustainability of program management practices Skills & Experience You Should Possess 10+ years of progressive project and program management experience leading complex technology initiatives Demonstrated success establishing PMOs, governance structures, integrated delivery plans, and program controls Experience leading large-scale cross-functional programs involving multiple stakeholders and third-party vendors Strong expertise in schedule management, risk management, dependency management, issue resolution, and executive reporting Experience supporting testing, deployment readiness, pilot programs, implementation activities, and go-live events Excellent stakeholder management, facilitation, communication, and presentation skills Ability to operate independently and deliver results in rapidly changing environments Strong analytical thinking, organizational skills, and problem-solving capabilities Experience leveraging Microsoft collaboration tools and AI-enabled productivity technologies Bonus Points If You Have Direct experience leading Point-of-Sale (POS) implementation, replacement, or modernization programs Experience within retail technology, restaurant operations, multi-site deployments, franchise operations, or carwash technology environments Experience implementing enterprise rollout strategies across geographically dispersed locations Familiarity with change management and organizational adoption initiatives Experience utilizing Microsoft Copilot or other AI-enabled project and program management tools Education & Certifications You Need Bachelor's degree in Information Technology, Business, Project Management, Computer Science, or a related discipline PMP (Project Management Professional), PgMP, PMI-ACP, or equivalent project/program management certification preferred Agile, Scrum, SAFe, or related delivery certifications are highly desirable What We Offer At Trissential, we believe talented professionals do their best work when they are empowered to lead, innovate, and make a measurable impact. By joining our client's team, you'll work on a highly visible transformation initiative while enjoying a supportive and collaborative environment. Competitive Compensation – You choose the model that works best for you, both with company-sponsored benefits! $129,000-$139,000 annually or $76-$86 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 This role is only open to candidates who are authorized to work in the United States. Ready to be part of something exciting? If you're passionate about leading enterprise transformation programs, driving successful deployments, and leveraging modern technologies to improve outcomes, apply today and take the next step in your career with Trissential.