Senior GTM Program Manager — Transformation & Alignment

Jackalope Digital LLC; Chicago, Northern (IL, KY); Hybrid; USD 120,000 - 180,000; Full time

Job summary

Stripe is seeking a senior-level program manager to lead large-scale GTM planning initiatives in the Chicago area. You will drive day-to-day operations, develop detailed roadmaps, and coordinate across Sales, Finance, Product, and Legal to ensure successful delivery of strategic programs.

The role requires strong analytical skills, pragmatism, and the ability to influence stakeholders while managing multiple initiatives in a fast-growing environment.

Qualifications

• 7+ years of program management, business operations, or management consulting experience, preferably in a GTM/Sales Operations organization.
• Demonstrated organizational, project management and execution skills with ability to own cross-functional projects.
• Ability to drive sales territory planning and align strategies across all segments to ensure seamless execution.
• Strong track record as a strategic, analytical problem solver and skilled operator with the demonstrated ability to successfully deploy new initiatives end to end.
• Comfort working quickly in a high growth and fast-paced environment.
• Ability to transition from high level to detailed work and willingness to “roll up your sleeves.”
• Detail-oriented with business acumen and ability to influence and communicate within all levels of the organization.

Responsibilities

• Lead and manage day-to-day operations of large-scale transformational projects.
• Develop detailed project plans, set milestones, and ensure program integrity.
• Standardize reporting and systems requirements.
• Design solutions for process improvements and tool development focusing on long-term sustainability and scalability of planning.
• Analyze and evaluate emerging challenges and opportunities, focusing on long term repeatable processes.
• Coordinate with key stakeholders and leadership to align complex programs and secure buy-in, while balancing prioritization.
• Partner cross-functionally across all departments to influence and execute.
• Be accountable for building and driving large-scale transformational initiatives end to end.
• Create strong business cases and drive influence to gain cross-functional support and resources needed to accomplish goals; use data to influence decisions.
• Proactively identify, assess, and mitigate risks that could impact successful delivery of programs.
• Create roadmaps, project plans, change management plans, tasks and reporting methodologies to track progress.
• Execute through cross-functional teams.
• Manage change management activities across stakeholder engagement, including messaging/communication planning, support and enablement.
• Influence and adopt the use of tooling, including AI-based levers, to make planning processes more efficient.

Skills

Program management

Cross-functional coordination

Analytical thinking

Strategic problem solving

Fast-paced environment

Detail orientation

Communication across organization

Tools

CRM systems

SQL

Google Sheets/Excel

Job description

Stripe is seeking a senior-level program manager to lead large-scale GTM planning initiatives in the Chicago area. You will drive day-to-day operations, develop detailed roadmaps, and coordinate across Sales, Finance, Product, and Legal to ensure successful delivery of strategic programs.

The role requires strong analytical skills, pragmatism, and the ability to influence stakeholders while managing multiple initiatives in a fast-growing environment.