Program Manager - POS Transformation

Trissential; Chicago (IL); Remote; USD 129,000 - 139,000; Full time

Benefits offered by this job

Competitive compensation

Comprehensive benefits

Paid holidays & PTO

Career development

Job summary

Trissential is seeking a Program Manager - POS Transformation to lead a high-visibility POS modernization initiative for a client. You will own the program mobilization, establish governance, drive pilot deployment, and introduce AI-enabled program management practices that improve delivery across the organization.

Work with senior leaders, technology teams, operations, and vendors to shape delivery methodologies, dashboards, and deployment strategies.

Qualifications

• 10+ years of progressive project and program management experience
• Experience establishing PMOs, governance structures and integrated delivery plans
• Experience with cross-functional programs involving vendors and multi-stakeholders
• Strong communication and executive reporting skills

Responsibilities

• Mobilize program and establish PMO with governance structures
• Lead pilot planning and deployment across technology, operations, and vendor workstreams
• Coordinate cross-functional teams and manage dependencies and risks
• Drive AI-enabled planning, reporting and knowledge management
• Deliver transparent executive-level status reports and milestones
• Foster continuous improvement and scalable deployment processes

Skills

Program management

Stakeholder management

Executive reporting

Risk management

Scheduling & planning

AI-enabled PM

Problem solving

Education

Bachelor's degree

PM certification preferred

Tools

Microsoft Copilot

Teams/SharePoint/Planner

Job description

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.