RFP, Content Strategist

PayPal • Chicago, IL

72d • $94,000 - $156,200 • Hybrid

About The Position

We are seeking a highly skilled and motivated Proposal Strategist to join our Commercial Strategy & Execution team. This role is pivotal in advancing high-value sales opportunities through the development of strategic, persuasive, and customer-aligned content, including RFP responses and other assets. The ideal candidate thrives in a fast-paced environment, demonstrates strong writing acumen, and has a proven ability to collaborate effectively across geographies and functions.

Requirements

• Minimum of 5 years of relevant work experience and a Bachelor's degree or equivalent experience.

Nice To Haves

• 5-7 years of experience in proposal development, content strategy, or related roles in enterprise sales environments.
• Demonstrated excellence in business writing, particularly in high-stakes, client-facing content.
• Mastery of RFP response tools (Loopio experience strongly preferred); proficiency with ChatGPT, Claude, Perplexity, and other LLMs or AI-based tools.
• Experience in Fintech, SaaS, or other technology-driven industries is highly desirable.
• Strong organizational skills and attention to detail, with a track record of meeting tight deadlines.
• Proven ability to work independently and manage ambiguity.

Responsibilities

• Analyze sales data to recommend process improvements.
• Collaborate with internal teams to enhance operational efficiency.
• Prepare detailed reports for management review.
• Handle complex customer inquiries and provide solutions.
• Mentor junior analysts and guide their professional growth.
• Lead the end-to-end development of Request for Proposal (RFP) responses, ensuring alignment with customer requirements, brand tone, and strategic priorities.
• Draft and tailor executive-facing pitch materials, including executive summaries, cover letters, presentation content, value propositions and messaging frameworks.
• Translate complex solutions into clear, compelling narratives that resonate with C-level decision-makers.
• Maintain and enhance content in our RFP knowledge base (Loopio), ensuring accuracy, relevance, and consistency.
• Collaborate closely with cross-functional stakeholders including Sales, Legal, Product, and Marketing to gather inputs and validate content.
• Manage multiple high-priority projects simultaneously, often under tight deadlines and evolving requirements.
• Adapt to the needs of a globally distributed team, contributing to a high-performing, collaborative culture across time zones.

Benefits

• Flexible work environment
• Employee shares options
• Health and life insurance
• Annual performance bonus (or other incentive compensation, as applicable)
• Equity
• Medical, dental, vision, and other benefits

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Industry: Credit Intermediation and Related Activities
• Education Level: Bachelor's degree
• Number of Employees: 5,001-10,000 employees