Overview

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