Program Manager - POS Transformation

Expleo • Chicago, IL

1d • 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, PMO establishment, governance, integrated planning, pilot deployment readiness and execution, and preparation for future rollouts. The Program Manager coordinates business, technology, operations, leadership, and vendor stakeholders, while creating sustainable delivery processes and providing transparent executive reporting.

The position also uses Microsoft Copilot and other AI-enabled tools to improve program planning, scheduling, reporting, documentation, knowledge management, and decision-making. AI-generated information must be validated against authoritative program sources, and AI-enabled processes must comply with security, confidentiality, and organizational policies. The role is fully remote, with Chicago, Illinois preferred, and is open only to candidates 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 with 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 work independently and deliver results in rapidly changing environments.
• Strong analytical thinking, organizational, and problem-solving capabilities.
• Experience with Microsoft collaboration tools and AI-enabled productivity technologies.
• Bachelor's degree in Information Technology, Business, Project Management, Computer Science, or a related discipline.
• Authorized 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 preferred.
• Agile, Scrum, SAFe, or related delivery certifications are highly desirable.

Responsibilities

• Assess the program's current scope, schedules, stakeholders, vendors, dependencies, risks, and delivery health.
• Establish a practical program management framework and sustainable PMO processes, tools, and controls.
• Develop and maintain integrated plans across multiple workstreams and stakeholder groups.
• Design governance structures, escalation pathways, decision-making processes, and reporting frameworks.
• Create executive dashboards, KPIs, status reports, and performance-tracking mechanisms.
• Establish clear ownership, accountability, and alignment across internal teams and vendor partners.
• Lead planning and execution activities for pilot deployment readiness.
• Manage integrated schedules across technology, testing, operations, implementation, and vendor workstreams.
• Coordinate store readiness, deployment preparation, launch support, and post-launch stabilization.
• Identify critical-path items, risks, dependencies, and mitigation strategies; drive issue resolution and escalation.
• Facilitate milestone reviews, readiness assessments, and go/no-go decisions.
• Capture lessons learned and create repeatable deployment processes for future rollouts.
• Use AI-powered tools to improve planning, scheduling, reporting, documentation, and execution; validate AI-generated outputs before executive distribution or decision-making.
• Use AI-assisted workflows to prepare executive communications, dashboards, and updates, improve knowledge management, and support meeting preparation and action tracking.
• Coordinate leadership, business partners, technology groups, and external vendors; drive accountability for milestones, deliverables, and commitments.
• Communicate complex technical concepts to non-technical stakeholders and provide transparent executive reporting on program health, risks, decisions, progress, and milestones.
• Use Microsoft Teams, SharePoint, Planner, Microsoft Copilot, and related collaboration technologies.
• Develop reusable governance practices, reporting frameworks, templates, and deployment artifacts.
• Ensure AI-enabled delivery processes comply with security, confidentiality, and organizational policies.
• Support knowledge transfer and the long-term sustainability of program management practices.

Benefits

• Competitive compensation: $129,000–$139,000 annually or $76–$86 per hour, with company-sponsored benefits; final compensation depends on skill alignment, experience, and geography.
• Medical plans, dental insurance, vision insurance, and an HSA with company contribution.
• Company-sponsored life insurance and short- and long-term disability insurance.
• Voluntary legal, hospital, accident, and pet wellness plans.
• 401(k) with matching.
• Paid holidays and paid time off.
• Career development and advancement opportunities.
• Supportive, collaborative team culture.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior