Proposal Lead

Stripe
Chicago +1 more
Career-pivot friendly

Who this role is best for

Aimed at experienced bid management professionals who can coordinate cross-functional teams and translate technical capabilities into business outcomes. The role is based in Chicago and Atlanta, with a focus on large-scale pursuits and strategic alignment with customer needs.

Best fit for

  • Experienced bid managers with a track record of handling large-scale pursuits and cross-functional coordination
    — “Experience managing complex, large-scale bids from initial evaluation through submission”
  • Candidates who can synthesize technical details into persuasive value propositions for enterprise clients
    — “Translate customers’ business and technical requirements into clear, persuasive proposals that communicate Stripe’s value and competitive advantages”
  • Professionals with strong project management skills and a history of delivering within tight deadlines
    — “balance strategic thinking with detailed execution while managing multiple deadlines and priorities”

Things to consider

  • The role demands a deep understanding of payments and SaaS products, which may require prior domain experience
    — “Experience working with payments or software-as-a-service (SaaS) products”
  • There is a potential expectation for process improvement based on win and loss data analysis
    — “using win and loss data to identify opportunities for improvement”

How to stand out

  • Emphasize experience in translating technical capabilities into measurable business outcomes
    — “translate Stripe's technical capabilities into measurable business outcomes”
  • Showcase leadership in cross-functional coordination and proposal reviews
    — “Lead proposal reviews, resolve blockers, and keep contributors aligned”
  • Highlight prior work in improving bid management processes and tools
    — “Improve proposal processes, templates, tools, and performance reporting”
Pace · Fast PacedCollaboration · HighAutonomy · MediumDecision Impact · Company

Derived from job-description analysis by Serendipath's career intelligence engine.

What success looks like

  • lead complex bid processes
  • improve proposal processes
Typical background
10+ years of experience in bid managementstrong proposal writing skills

Skills & requirements

Required

Bid ManagementProposal DevelopmentCross-functional CoordinationValue Proposition

Preferred

Bid Management SoftwarePricing Strategy

Stack & domain

Bid ManagementDeal ManagementProcurementPricing StrategyFinancial ConsultingLegal ServicesProposal WritingProject ManagementBid And Deal LifecycleCross-functional CoordinationCommunication With Senior StakeholdersPayments ProductsSaas ProductsBid Management SoftwarePricing And Commercial StrategiesComplex Payments ProductsUse CasesStrategic ThinkingDetailed ExecutionManaging Multiple Deadlines And PrioritiesPgmpPMPPaymentsSoftware-as-a-service (saas)

About the role

Original posting from 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

Source: Stripe careers

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