Program Manager – POS Transformation

Trissential

. Assess the current state of the POS transformation program, including scope, schedules, stakeholders, vendors, dependencies, risks, and delivery health .

Posted 10/23/2026full-timeRemote • Illinois • United StatesSeniorLead💰 $129,000 - $139,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive experience in program management, including establishing PMOs, governance structures, and integrated delivery plans. Proficient in leveraging AI-enabled tools for planning, reporting, and stakeholder communication while ensuring alignment with organizational policies.

Highest-signal resume keywords

Program ManagementStakeholder ManagementRisk ManagementSchedule ManagementGovernance Structures

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Project ManagementProgram ControlsDependency ManagementIssue ResolutionExecutive ReportingDeployment ReadinessAnalytical ThinkingProblem-SolvingIntegrated Delivery PlansTesting Support

Soft Skills

Communication SkillsFacilitation SkillsPresentation SkillsOrganizational SkillsAccountability

Tools & Technologies

Microsoft Collaboration ToolsAI-Powered ToolsExecutive DashboardsPerformance-Tracking MechanismsDocumentation Quality Tools

Certifications & Qualifications

PMPPgMPPMI-ACPAgile CertificationScrum Certification

Industry Keywords

POS TransformationCross-Functional ProgramsVendor ManagementDeployment ArtifactsGovernance Practices

Tech Stack

Tools & technologies

PMP

About the role

Key responsibilities & impact

Assess the current state of the POS transformation program, including scope, schedules, stakeholders, vendors, dependencies, risks, and delivery health
Establish a sustainable program management framework and PMO processes
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
Lead planning and execution for POS 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, delivery risks, dependencies, and mitigation strategies
Facilitate milestone reviews, readiness assessments, and go/no-go decisions
Drive issue resolution and escalation management
Capture lessons learned and establish repeatable deployment processes for future rollouts
Leverage AI-powered tools to improve planning, scheduling, reporting, documentation, and execution
Analyze program data to identify emerging risks and mitigation opportunities
Create executive communications, status reports, dashboards, and updates using AI-assisted workflows
Improve knowledge management, documentation quality, and information accessibility
Enhance meeting preparation, action tracking, and follow-up management
Validate AI-generated outputs against authoritative program information before executive distribution or decision-making
Coordinate leadership teams, business partners, technology groups, and external vendors
Drive accountability for milestones, deliverables, and execution commitments
Communicate complex technical concepts to non-technical stakeholders
Deliver transparent executive-level reporting on program health, progress, risks, decisions, and milestones
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

Requirements

What you’ll need

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
Bachelor's degree in Information Technology, Business, Project Management, Computer Science, or a related discipline
This role is only open to candidates who are authorized to work in the United States
PMP, PgMP, PMI-ACP, or equivalent certification preferred
Agile, Scrum, SAFe, or related delivery certifications highly desirable

Benefits

Comp & perks

Comprehensive medical plans
Dental insurance
Vision insurance
HSA with company contribution
Company-sponsored life insurance
Short-term and long-term disability insurance
Voluntary legal, hospital, accident, and pet wellness plans
401(k) with matching
Paid holidays
Paid time off
Career development and advancement opportunities
Strong team culture
Remote work