Senior GTM Transformation Program Manager

WinsAbove; Chicago, Northern (IL, KY); Hybrid; USD 140,000 - 190,000; Full time

Job summary

Stripe is seeking a Senior Program Manager to lead day-to-day operations of large-scale transformational projects and drive cross-functional programs in Chicago. You will partner with Sales Ops, Finance, Product, and Legal to build scalable planning processes and improve reporting.

The role emphasizes strategic problem solving, data-driven decisions, and the ability to roll up your sleeves in a fast-paced environment. Strong collaboration across departments is essential.

Qualifications

• 7+ years of program management or related experience.
• Experience in GTM/Sales Operations preferred.
• Ability to drive cross-functional programs and initiatives.

Responsibilities

• Lead day-to-day operations of large-scale transformational projects
• Develop detailed project plans, milestones and program integrity
• Standardize reporting and systems requirements
• Design solutions for process improvements and scalable planning
• Coordinate with stakeholders and leadership to align programs
• Partner cross-functionally to influence and execute
• Create roadmaps and reporting methodologies for progress tracking
• Manage change management activities across teams
• Adopt AI-based levers to improve planning efficiency

Skills

Program management

Business operations

Management consulting

Cross-functional leadership

Analytical thinking

Detail-oriented

Communication

Tools

CRM systems

SQL

Excel

Job description

Stripe is seeking a Senior Program Manager to lead day-to-day operations of large-scale transformational projects and drive cross-functional programs in Chicago. You will partner with Sales Ops, Finance, Product, and Legal to build scalable planning processes and improve reporting.

The role emphasizes strategic problem solving, data-driven decisions, and the ability to roll up your sleeves in a fast-paced environment. Strong collaboration across departments is essential.