Jobs › Stripe

Strategy & Operations Business Partner, Customer Success

Stripe · Chicago, IL · 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 an annual planning cycle you led. How did you get leaders to agree on tradeoffs?

What they are checking: Whether they can drive hard decisions through a group of leaders with different priorities.

Tell me about a time you were a thought partner to a senior leader and changed their mind.

What they are checking: Whether they act as a real business partner who brings independent judgment, not just support.

How do you stay hands-on with data while also leading strategy?

What they are checking: Whether they can still do their own analysis instead of only directing others.

What would you do

The CS leader asks why net retention dropped last quarter. How would you find the answer?

What they are checking: Whether they can break a messy business question into parts and test each one with data.

Sales and CS disagree on who owns expansion revenue. How would you help settle it?

What they are checking: Whether they can design clear ownership that both teams accept as fair.

About the work

How would you design the engagement model for Customer Success, meaning which users get a dedicated CSM and which get pooled or digital coverage?

What they are checking: Whether they can match coverage to user value and need while keeping cost under control.

Walk me through how you'd approach compensation design for CSMs. What would you reward?

What they are checking: Whether they understand how incentives shape behavior, including retention versus expansion tradeoffs.

How do you design a territory model for a customer success team that's growing fast?

What they are checking: Whether they balance workload, fairness and user coverage when carving up accounts.

How do you run leadership forums so they produce decisions rather than status updates?

What they are checking: Whether they can design operating cadences that make leaders more effective.

What metrics would you put on a Customer Success scorecard, and which would you leave off?

What they are checking: Whether they know which metrics drive the right behavior and which ones mislead.

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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 The Customer Success team oversees the post-sales lifecycle for Stripe users, ensuring they realize the maximum value of their investment. This partnership drives user success, increases retention and expansion, and supports mutually beneficial renewal outcomes. Few teams provide such a direct impact on the growth of the company. The Customer Success Strategy & Operations team sits at the center of how Customer Success operates at Stripe. This role shapes both the function’s day-to-day operating model—from leadership forums and territory and compensation design to the systems and cadences that enable execution—and its long-term direction. You will lead annual planning, OKR development, and engagement-model design to ensure CS is positioned to deliver for users and scale effectively. This is a true ‘Business Partner’ role; you will serve as a trusted thought partner to Customer Success leadership—combining strategic insight, operational rigor, and hands-on execution. You will help translate CS priorities into actionable plans, drive cross-functional initiatives, and build the operating mechanisms that enable teams to make better decisions, execute consistently, and scale effectively. If you enjoy moving between strategic problem-solving and hands-on execution—and bring a roll-up-your-sleeves mindset—this role is for you. What you’ll do The near-term focus of this role is on evolving and scaling the foundations of the Customer Success business. This includes strengthening operating models, processes, business cadences, systems, and reporting infrastructure to support a growing and increasingly specialized organization. As a key business partner, you’ll measure and analyze performance, develop forecasts and dashboards, and lead data-informed process improvements that help the CS team operate more efficiently and deliver greater customer impact. Responsibilities • Work cross-functionally to analyze and troubleshoot system challenges • Define operating models for new Customer Success specialisms, including metrics, processes, and cross-functional ways of working • Design and implement AI-enabled workflows that improve CSM efficiency, scalability, and customer impact • Conduct analysis and investigation of system operations and workflow management • Translate business needs into scalable technical solutions and lead their implementation from requirements through delivery • Develop scalable, automated reports and dashboards that meet key business and leadership reporting requirement, and reduce manual effort and operational overhead • Oversee the management of CSM territories • Enhance business processes through data-driven decision-making • Define and monitor annual and quarterly OKRs • Prepare materials for QBRs and other leadership meetings 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 work experience, with a significant portion in strategic / operational roles at high-growth tech companies or consulting. • High comfort with ambiguity—you take an undefined operational problem, scope it, design a solution, and drive it to completion with minimal oversight. • Experience with and holding a high bar across operational design, strategic planning, and reporting. • You are comfortable working independently with minimal oversight while holding yourself accountable to deadlines. • Experience working cross functionally with senior stakeholders. You're comfortable bringing an independent and opinionated perspective. • Technical proficiency in AI tools in order to automate workflows as needed. • Strong analytical rigor—you're comfortable owning data and metrics directly, running your own analyses, and pressure-testing assumptions without relying on a dedicated analytics partner • Ability to manage technical resources and translate business needs into requirements Preferred qualifications •  Experience working with Go-to-Market teams including Customer Success •  Proficient in SQL

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