Jobs › Stripe

Proposal Lead

Stripe · Chicago, IL · 1530 GTM Industries

Posted Sep 25, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a proposal where you shaped the strategy and narrative, not just the formatting.

What they are checking: Whether they can build a winning story, which the posting calls proposal strategy.

Tell me about a time you had to push back on a senior salesperson's approach to a proposal.

What they are checking: Whether they can hold a quality bar with senior partners respectfully.

What do you do after a loss to learn from it?

What they are checking: Whether they seek feedback and improve future proposals instead of moving on silently.

What would you do

How do you decide whether a proposal is worth responding to at all?

What they are checking: Whether they help the team qualify opportunities instead of answering every RFP.

A subject matter expert is late with critical answers and the deadline is two days away. What do you do?

What they are checking: Whether they can keep contributors accountable and find workarounds under pressure.

About the work

Walk me through how you'd run a large RFP from the day it arrives to submission.

What they are checking: Whether they have a repeatable process for complex proposals with many contributors.

How do you turn technical product capabilities into business outcomes a buyer cares about?

What they are checking: Whether they can write value-led answers rather than lists of features.

How would you build a content library so the team isn't rewriting the same answers every time?

What they are checking: Whether they can improve tools and templates so proposals scale, as the role requires.

How do you make sure security, legal and compliance answers in a proposal are accurate?

What they are checking: Whether they protect the company from making promises it cannot keep.

How do you keep a proposal consistent in voice when many people have written parts of it?

What they are checking: Whether they can edit for one clear voice across many contributors.

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The full job description

As published by Stripe.

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

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