Stripe Verified

Fintech, Payments, Software-as-a-Service (SaaS)

Proposal Lead

Chicago, ILOnsiteFull TimeLeadPosted 1 month agoVisa sponsorship available

Is this role right for you?

Upload your resume and get a skill-by-skill breakdown — see exactly where you match, where you're close, and what to highlight. Not a mystery percentage.

Get a tailored resume highlighting what this role needs.

Required skills

bid management
deal management
procurement
pricing strategy
financial consulting
legal services
proposal writing
project management
cross-functional contributors
senior stakeholders

Nice to have

payments
software-as-a-service
SaaS
ambiguous environment
bid management software
complex payments products

Role summary

Stripe is seeking a Proposal Lead to manage RFPs and RFIs for their largest clients. This role involves developing proposal strategies, coordinating cross-functional teams (sales, legal, security, etc.), and delivering high-quality submissions that articulate Stripe's value proposition. The Lead will also be responsible for improving proposal processes, templates, and tools, leveraging data to drive enhancements. The ideal candidate possesses strong project management and proposal writing skills, with at least 10 years of experience in bid management, deal management, procurement, or a related field. Experience in payments or SaaS is preferred.

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

Sample Stripe interview questions

1
Discuss failure modes and backward compatibility for a system design.
system designeasy
2
How do you see customer expectations shifting in the coming years?
technicalmedium
3
Discuss your solution, coding approach, problem-solving process, and technical decision-making for the coding challenge.
technicaleasy
4
What are important metrics to analyze to measure pipeline and deal signed health
metrics analyticsdifficult

Get started to unlock a personalized interview prep pack for this role.

Ready to apply?

You'll be redirected to Stripe's application page.