Stripe
Fintech & PaymentsDirect Greenhouse career site

Proposal Lead

Location
Chicago, IL · On-site
Job type
Full-time
Level
Director
Experience
10+ years
Education
Bachelor's degree
Listed
30 days ago

Skills & highlights for this role

  • bid management
  • RFP/RFI response
  • proposal writing
  • pricing strategy
  • project management

Also useful

  • bid management software
  • PgMP
  • PMP
  • payments/SaaS

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

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.

Read the original posting

From Stripe's careers page, first listed on Rolev.ai on October 10, 2026. Rolev.ai is not the employer.

How Rolev.ai helps with this application

Rolev.ai is a job search and application tool for US job seekers. For this Proposal Lead role at Stripe, it shows how your resume fits, tailors your resume to the posting, and prepares the application for you to review.

  • See how you fit

    Openings from employer career sites are ranked against your whole resume—and searchable inside Claude, ChatGPT, and Cursor via Rolev.ai MCP.

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Common questions

Where is the Proposal Lead job at Stripe located?

This Proposal Lead position at Stripe is located in Chicago, IL (On-site). Always check Stripe's application page for specific state eligibility or relocation policies.

What qualifications are required for Proposal Lead at Stripe?

For the Proposal Lead role, Stripe highlights 10+ years of relevant experience; a bachelor's degree; experience with bid management, RFP/RFI response, proposal writing, pricing strategy, project management. Rolev.ai can score your existing resume against these requirements and show any skill gaps before you apply.

How do I apply for the Proposal Lead position at Stripe?

This listing links directly to Stripe's Greenhouse application page. You can apply directly on Stripe's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Greenhouse application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.