Renewals Specialist

Stripe•Chicago, IL

About The Position

The Renewals Specialist partners with account teams and cross-functional stakeholders to protect and grow Stripe’s revenue from existing users. The role is analytical, combining quantitative analysis and financial modeling with user context to assess renewal options, identify risks and opportunities, and support well-founded commercial decisions. It involves working on large, complex renewals while balancing Stripe’s and users’ needs and helping account teams move deals forward on schedule. The specialist applies strong judgment and attention to detail, builds trusted relationships across teams, operates in ambiguous situations, respectfully challenges assumptions, and contributes to constructive debate. The role also supports the design of scalable renewal processes that can accommodate fluctuating volumes while maintaining operational excellence.

Requirements

6+ 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 and 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, constructively challenge assumptions, and help teams reach sound decisions.
Strong organizational and time-management skills, including experience prioritizing multiple time-sensitive workstreams, meeting deadlines, maintaining accuracy, and improving supporting processes.

Nice To Haves

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.

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 working relationships across Sales, Customer Success, Deal Pricing, Deal Strategy, and technical and operational teams involved in the renewal lifecycle.
Report on renewal performance, risks, and recommendations through weekly, monthly, and quarterly updates.
Identify and implement scalable improvements to renewal workflows through tooling, automation, and responsible use of AI-assisted solutions.
Contribute to a team culture grounded in ownership, integrity, intellectual honesty, and collaboration.