Program Manager - POS Transformation

Expleo•Chicago, IL

3d•$129,000 - $139,000•Remote

About The Position

Trissential is seeking a Program Manager to lead a high-visibility, enterprise-wide Point-of-Sale (POS) modernization initiative for a client. The role owns program mobilization, governance, integrated planning, pilot deployment readiness and execution, vendor coordination, executive reporting, and sustainable delivery practices. The position is fully remote, with Chicago, Illinois preferred, and involves partnering with business, technology, operations, leadership, and third-party vendor teams. The Program Manager will assess program health and establish practical PMO frameworks, governance, reporting, and accountability. They will coordinate workstreams through pilot launch and stabilization, manage risks and dependencies, support go/no-go decisions, and create repeatable practices for future deployments. They will also use Microsoft Copilot and other AI-enabled tools to improve planning, documentation, reporting, and execution, ensuring AI-generated content is validated and that processes comply with security, confidentiality, and organizational policies. The role requires 10 or more years of progressive project and program management experience leading complex technology initiatives. A bachelor's degree in a relevant discipline is required. PMP, PgMP, PMI-ACP, or equivalent certification is preferred; Agile, Scrum, SAFe, or related certifications are highly desirable. Compensation is listed as $129,000–$139,000 annually or $76–$86 per hour, with the final amount determined by skills, experience, and geography. Candidates must be authorized to work in the United States.

Requirements

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, risk, and 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.
Bachelor's degree in Information Technology, Business, Project Management, Computer Science, or a related discipline.
Authorization to work in the United States.

Nice To Haves

Direct experience leading POS implementation, replacement, or modernization programs.
Experience in retail technology, restaurant operations, multi-site deployments, franchise operations, or carwash technology.
Experience implementing enterprise rollout strategies across geographically dispersed locations.
Familiarity with change management and organizational adoption initiatives.
Experience using Microsoft Copilot or other AI-enabled project and program management tools.
PMP, PgMP, PMI-ACP, or equivalent project/program management certification.
Agile, Scrum, SAFe, or related delivery certifications.

Responsibilities

Assess the POS transformation program's scope, schedules, stakeholders, vendors, dependencies, risks, and delivery health.
Establish a practical, sustainable program management framework and develop integrated plans across workstreams and stakeholder groups.
Design governance structures, escalation pathways, decision-making processes, reporting frameworks, executive dashboards, KPIs, and performance tracking.
Establish clear ownership, accountability, and execution alignment across internal teams and vendor partners.
Lead planning and execution activities for POS pilot deployment readiness, including integrated scheduling across technology, testing, operations, implementation, and vendor workstreams.
Coordinate store readiness, deployment preparation, launch support, and post-launch stabilization.
Identify critical path items, delivery risks, dependencies, and mitigation strategies; drive issue resolution and escalation management.
Facilitate milestone reviews, readiness assessments, and go/no-go decision processes.
Capture lessons learned and establish repeatable deployment processes for future rollouts.
Use AI-powered tools to improve planning, scheduling, reporting, documentation, execution, knowledge management, meeting preparation, action tracking, and follow-up.
Analyze program data to identify emerging risks, dependency challenges, and mitigation opportunities.
Validate AI-generated outputs against authoritative program information before executive distribution or decision-making.
Serve as the primary coordination point among leadership, business partners, technology groups, and external vendors.
Drive accountability for program milestones, deliverables, and execution commitments; communicate technical concepts effectively to non-technical stakeholders.
Provide transparent executive-level reporting on program health, progress, risks, decisions, and milestones.
Use Microsoft Teams, SharePoint, Planner, Microsoft Copilot, and related collaboration technologies.
Ensure AI-enabled delivery processes meet security, confidentiality, and organizational policy requirements.
Support knowledge transfer and the long-term sustainability of program management practices.