Proposal Lead

WinsAbove; Chicago, Northern (IL, KY); Hybrid; USD 120,000 - 160,000; Full time

Job summary

Stripe seeks a Proposal Lead to manage RFPs/RFIs for its largest pursuits. You will develop strategy and narratives, coordinate across Stripe, and deliver high-quality submissions addressing customer requirements.

You will improve processes, templates, and tools for scalable bid management while building trusted relationships with stakeholders. The role requires translating complex customer needs into persuasive proposals, coordinating legal, privacy, security, and sales teams, and delivering

Qualifications

• 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.

Responsibilities

• Lead end-to-end bid management process from invitation to submission.
• Translate customer requirements into clear, persuasive proposals communicating Stripe’s value.
• Develop proposals including executive summaries, value propositions, and pricing recommendations.
• Coordinate contributors across sales, solutions architecture, legal, privacy, security, and other functions.
• Lead proposal reviews, resolve blockers, and meet deadlines while aligning contributors.
• Develop proposals that connect customer needs with Stripe’s products and capabilities.
• Improve proposal processes, templates, and tools using win/loss data.

Skills

Proposal writing

Project management

Bid management

Cross-functional coordination

Stakeholder communication

Education

Bachelor’s degree or equivalent

Tools

Bid management software

Job description

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 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.

What you’ll do

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.

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

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

• 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

Preferred qualifications

• 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