Remote POS Transformation AI PMO Lead

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

Benefits offered by this job

Competitive compensation and benefits

Job summary

Trissential, LLC is seeking an experienced Program Manager to lead a nationwide POS transformation initiative. You will own governance, pilot planning, and cross-functional delivery, partnering with executives and vendors to drive outcomes.

You will guide scheduling, risk management, and reporting while leveraging AI-powered tools to enhance decision-making and execution across multiple locations.

Qualifications

• 10+ years leading complex technology initiatives.
• Experience establishing PMOs, governance, and integrated plans.
• Experience leading multi-stakeholder programs with third-party vendors.
• Strong schedule, risk, dependency management and executive reporting.
• Experience supporting testing, pilot programs, and go-live events.
• Excellent stakeholder management and communication skills.
• Ability to work independently in fast-changing environments.
• Experience leveraging Microsoft tools and AI-enabled productivity.

Responsibilities

• Lead a high-visibility POS transformation program with executive sponsorship.
• Establish governance structures, PMO processes, and reporting frameworks.
• Plan and execute POS pilot deployments across locations and vendors.
• Collaborate with business leaders, technology teams, and operations.
• Leverage AI-enabled tools to improve planning, reporting, and delivery.

Skills

Program management

Stakeholder mgmt

Executive reporting

Risk management

Schedule management

AI-enabled tools

Change management

Cross-functional leadership

Education

Bachelor's degree in IT/CS/Business

PMP/PgMP/PMI-ACP certification

Tools

Microsoft Copilot

Microsoft Teams

SharePoint

Planner

Job description

Trissential, LLC is seeking an experienced Program Manager to lead a nationwide POS transformation initiative. You will own governance, pilot planning, and cross-functional delivery, partnering with executives and vendors to drive outcomes.

You will guide scheduling, risk management, and reporting while leveraging AI-powered tools to enhance decision-making and execution across multiple locations.