Proposal Lead

Stripe • Chicago, IL

7d

About The Position

The Business Value Consulting and Proposals team supports long-term growth and value creation for Stripe’s largest and most strategic users. We translate Stripe's technical capabilities into measurable business outcomes and create value-led proposals that help secure and expand relationships with leading organizations. As a Proposal Lead, you’ll manage requests for proposals and requests for information (RFPs and RFIs) for Stripe’s largest pursuits. You’ll develop proposal strategy and narratives, coordinate contributors across Stripe, and deliver high-quality submissions that address customer requirements. You’ll also improve the processes, templates, and tools that help Stripe manage proposals consistently and at scale. You’ll bring structure to complex pursuits, build trusted relationships, and communicate clearly with contributors and leaders. This role is a good fit for someone who can balance strategic thinking with detailed execution while managing multiple deadlines and priorities.

Requirements

• Bachelor’s degree or equivalent experience
• 10+ years of experience in bid management, deal management, procurement, pricing strategy, financial consulting, legal services, or a related field
• Experience managing complex, large-scale bids from initial evaluation through submission
• Strong proposal writing and project management skills, with a clear understanding of the bid and deal lifecycle
• Experience coordinating cross-functional contributors and communicating effectively with senior stakeholders

Nice To Haves

• Experience working with payments or software-as-a-service (SaaS) products and improving processes in an ambiguous environment
• Experience with bid management software
• Knowledge of pricing and commercial strategies used in proposal development
• Experience communicating the value of complex payments products and use cases
• Program Management Professional (PgMP) or Project Management Professional (PMP) certification

Responsibilities

• Lead the end-to-end bid management process, including reviewing bid invitations, supporting bid or no-bid analysis, defining the response strategy, and establishing timelines
• Translate customers’ business and technical requirements into clear, persuasive proposals that communicate Stripe’s value and competitive advantages
• Develop proposal content, including executive summaries, value propositions, and recommendations related to pricing and commercial structure
• Coordinate contributors across sales, solutions architecture, legal, privacy, security, and other functions to produce complete and accurate responses to bid components
• Lead proposal reviews, resolve blockers, and keep contributors aligned to deliver high-quality submissions within required timelines
• Develop proposals that connect customer requirements with Stripe’s long-term goals, products, and capabilities
• Improve proposal processes, templates, tools, and performance reporting, using win and loss data to identify opportunities for improvement

What This Job Offers

• Job Type: Full-time