Jobs › Stripe

Program Manager, GTM Planning

Stripe · Chicago, IL · Remote available · 1520 Sales Operations (SS&O)

Posted Sep 25, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a large transformational project you led. How did you set milestones and keep it on track?

What they are checking: Whether they have managed big projects with real structure, as the posting requires.

Tell me about a process you redesigned to make it more scalable.

What they are checking: Whether they think about long-term sustainability, not just getting through this cycle.

How do you keep people engaged in a planning process that many see as a chore?

What they are checking: Whether they can make the process useful enough that people participate willingly.

What did you learn from the last planning cycle you were part of that you'd do differently?

What they are checking: Whether they reflect on their work and improve each cycle.

What would you do

Finance and Sales disagree on a quota assumption late in planning. How do you help resolve it?

What they are checking: Whether they can keep the process moving by bringing the right data and decision makers together.

A key deadline in the planning calendar is at risk. How do you communicate it?

What they are checking: Whether they raise risks early and offer options instead of surprises.

About the work

Walk me through how you'd manage a sales planning cycle across Sales, Finance, Product and Legal.

What they are checking: Whether they can coordinate many partners toward one planning outcome on time.

How would you standardize reporting when different teams track planning data in different ways?

What they are checking: Whether they can create shared definitions and systems that teams actually use.

How do you write systems requirements for a planning tool so engineers build the right thing?

What they are checking: Whether they can translate business needs into clear requirements.

How do you evaluate whether a process improvement actually worked?

What they are checking: Whether they measure results rather than assume a change helped.

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The full job description

As published by Stripe.

Who we are About Stripe Stripe is a financial infrastructure platform for businesses. Millions of companies - from the world’s largest enterprises to the most ambitious startups - use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career. About the team Stripe’s GTM Planning team partners with Sales Leadership, Finance, Product, and Legal to drive operational excellence to support our GTM strategy. We bring expertise, rigorous thinking, and a user-first approach to problem solving. We transform, improve and support global Stripe business processes to drive critical initiatives and other cross-functional business priorities for the sales planning cycle. What you’ll do • Project Management: • 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 • Identify needs and create solutions: • 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 • Stakeholder management: • Coordinate with key stakeholders and leadership to align complex programs and secure buy-in, while balancing prioritization • Partner cross-functionally across all departments (Finance, Legal, Systems, etc.) to influence and execute Responsibilities • 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 your goals; use data to influence decisions • Proactively identify, assess, and mitigate risks that could impact the 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 the planning processes more efficient Who you are We're looking for someone who meets the minimum requirements to be considered for the role. If you meet these requirements, you are encouraged to apply. The preferred qualifications are a bonus, not a requirement. Minimum requirements • 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 • An 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 • A high degree of comfort working quickly in a high growth and fast-paced environment • An ability to seamlessly transition from the high level to very detailed, and a willingness to “roll up your sleeves” • A detail-oriented and analytical individual with business acumen, and the ability to influence and communicate within all levels of the organization Preferred qualifications • Knowledge of Customer Relationship Manager (CRM) systems • Data Analytics (Google Sheets/Excel data manipulation, SQL)

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