Renewals Specialist at Stripe in Chicago

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 Renewals Team is a strategic partner to Stripe's Sales organization, helping Stripe retain and expand revenue from its portfolio of existing users. We bring analytical rigor, commercial judgment, and operational discipline to the renewal process so account teams can navigate complex decisions with clarity, accuracy, and speed.

We work closely with Sales, Deal Pricing, Deal Strategy, Customer Success and other cross-functional partners throughout the renewal lifecycle. The team analyzes account performance and contractual history, builds renewal scenarios, and develops recommendations that inform deal strategy and negotiation planning led by Account Executives. We also improve the systems and processes that enable Stripe to manage renewals at scale.

What you’ll do

As a Renewals Specialist, you will partner with account teams and cross-functional stakeholders to protect and grow Stripe's revenue. This is an analytical role at its core. You will combine quantitative analysis and financial modeling with user context to assess renewal options, identify risks and opportunities, and help teams make well-supported commercial decisions.

You will work on large, complex renewals, balancing the needs of Stripe and our users while helping account teams move deals forward on schedule. Success requires strong judgment, attention to detail, and the ability to build trusted relationships across teams. You should be comfortable operating in ambiguity, respectfully challenging assumptions, and engaging in constructive debate to reach better outcomes. You will also help design scalable processes so the team can handle fluctuating volumes while maintaining a high standard of operational excellence.

Responsibilities

• Partner with Account Executives to develop and execute strategies for retaining and expanding revenue from existing users.
• Manage a portfolio of upcoming renewals, tracking milestones, risks, dependencies, and stakeholder actions.
• Analyze historical pricing, product usage, account performance, and contractual terms to develop renewal recommendations.
• Build financial models and renewal scenarios that clarify commercial tradeoffs and support data-driven decisions.
• Partner on deal strategy and negotiation planning for large or complex renewals, providing analysis and a clear point of view to support commercial negotiations led by Account Executives.
• Identify retention risks, expansion opportunities, and changes in user needs by combining feedback from Sales and Customer Success with account-level data.
• Support accurate, timely quote and proposal development with account teams and cross-functional partners.
• Build strong working relationships across Sales, Customer Success, Deal Pricing, Deal Strategy, and the technical and operational teams involved in the renewal lifecycle.
• Report on renewal performance, risks, and recommendations through clear weekly, monthly, and quarterly updates.
• Identify and implement scalable improvements to renewal workflows through tooling, automation, and the responsible use of AI-assisted solutions.
• Contribute to a team culture grounded in ownership, integrity, intellectual honesty, and collaboration.

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

• 3+ years of experience in renewals, strategic account management, sales, customer success, or a related field, ideally in a high-growth technology environment.
• Strong analytical and critical-thinking skills, including proficiency in Excel or Google Sheets and experience building financial models, pricing analyses, or business cases that turn complex data into clear recommendations.
• Sound business judgment, with the ability to weigh competing priorities, risks, and tradeoffs in ambiguous situations.
• Strong interpersonal, written, and verbal communication skills, with the ability to build trust and influence partners without direct authority.
• Demonstrated ability to collaborate across functions while constructively challenging assumptions and helping teams reach sound decisions.
• Strong organizational and time-management skills, with demonstrated experience prioritizing multiple time-sensitive workstreams, meeting deadlines, maintaining accuracy, and improving the processes that support the work.

Preferred qualifications

• Experience in payments, financial services, or FinTech.
• Experience with contract renewals, pricing discussions, or complex deal structures.
• Familiarity with recurring-revenue or consumption-based business models, and with CRM, quoting, or business-intelligence tools.
• Comfort using AI-assisted tools to accelerate research, analysis, documentation, and process improvement, with sound judgment around accuracy and appropriate data handling.