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Proposal Specialist

CDW
Chicago, IL, USARemoteProject / Program ManagementEntry-Level$71,000 - $100,000Posted: today

About the role

As the "quarterback" of each pursuit, the Proposal Specialist leads the end-to-end proposal process for RFPs, RFIs, RFQs and similar solicitations, running color team reviews from assignment through submission, supporting post-submission activities and coordinating all resources across sales, technical, pricing, contracts, legal, program management, partners and vendors into one cohesive response. The role calls for both a strong persuasive writer and a disciplined project manager.

The Proposal Specialist uses content library/knowledge management platforms and company-approved generative AI tools to produce compliant, compelling, win-focused responses efficiently. The ultimate goal of the role is to increase win rates and drive revenue. What You Will Do: Opportunity Assessment & Planning Analyze solicitations for requirements, evaluation criteria, instructions and risks; build compliance matrices and outlines mapping each requirement to an owner. Research the customer's priorities, constraints and hot buttons, the incumbent and the competitive landscape.

Provide relevant context and input for sales-led bid/no-bid decisions. Proposal Leadership & Project Management Build a schedule backward from the due date, define roles and track actions, risks and dependencies. Manage concurrent proposals, hold contributors accountable without direct authority, escalate issues early. Color Team Review Process Plan, facilitate and adjudicate Kickoff, Pink (first draft), Red (final draft), Gold (page by page compliance); coordinate Green (pricing) reviews owned by sales or technical leads.

Strategy, Win Themes & Writing Work with the opportunity team to develop the win strategy, win themes, discriminators and value propositions. Write, edit and tailor persuasive, accurate, compliant content in one voice, aligned to evaluation criteria. AI & Content Library Use company-approved generative AI tools to analyze and deepen understanding of solicitations, draft and refine content, summarize requirements and speed up reviews. Verify AI output, protect confidential data, and grow the content library, templates and boilerplate.

Compliance, Production & Submission Ensure compliance with instructions, forms, certifications, formatting and page limits; manage final assembly, quality control and on-time submission, including via portals. Post-Submission Support Support clarifications, Q&A, orals, BAFOs and protests as needed, in a supporting rather than leading role. Request and conduct debriefs, capture lessons learned, support award transition and close out opportunities.

Department Contribution Join training, department and process-improvement initiatives, industry days and pre-proposal conferences; share best practices with peers. What We Expect of You: Minimum Basic requirements Bachelor's degree or equivalent relevant work experience. Two or more years of proposal writing, proposal management, project management, technical/business writing or editorial experience. Excellent writing, editing and verbal communication skills. Ability to manage multiple deadline-driven projects at the same time. Strong attention to detail and a focus on compliance.

Working proficiency with generative AI tools and a willingness to adopt new technology. Advanced proficiency in Microsoft Office (Word, Excel, PowerPoint, Teams, SharePoint) and Adobe Acrobat. Sound judgment, composure under pressure and constructive communication with all levels of the organization, including executives. Preferred skills, experience, and qualities needed Public sector or government procurement knowledge, including contracts, T&Cs and purchasing requirements. General knowledge of IT products, services and solutions.

Experience with proposal content/RFP response platforms and structured color team reviews (e.g., Shipley). APMP certification (Foundation or Practitioner) or PMI certification (CAPM or PMP).

Pay range: $71,000 - $100,000 depending on experience and skill set Annual bonus target of 5% subject to terms and conditions of plan Benefits overview: https://cdw.benefit-info.com/ Salary ranges may be subject to geographic differentials CDW is committed to being an AI-fluent organization We’re looking for people who bring curiosity, a learner’s mindset, and a willingness to engage with ever-evolving technology and tools. We value adopting AI as a partner, openness to experimentation, and a shared interest in learning together on AI.

Our goal is to create a culture where AI enhances—not replaces—human creativity and decision-making. You don’t need to be an expert today; what matters is your readiness to explore, adapt, and grow with us as we integrate AI responsibly and effectively into our work. Additionally, CDW is committed to fostering an equitable, transparent, and respectful hiring process for all applicants. During our application process, our goal is to understand your experience, strengths, skills, and qualifications.

As an AI forward company, we see AI not just as a tool, but as a catalyst for new ways of thinking, creating, and communicating. We encourage candidates to embrace an AI mindset, one that’s curious, adaptive, and ready to explore what’s possible. We welcome thoughtful use of AI to expand your perspective and elevate how you share your story, while ensuring your application remains rooted in your own background, judgment, and voice.

About Us CDW is a Fortune 500 technology solutions provider that helps businesses, government, education, and healthcare organizations achieve what’s possible through technology. What makes CDW different isn’t just what we do—it’s how we do it. At CDW we act as one—building trust, speaking candidly, and working together to achieve more. We play to win—focusing on what matters most and delivering for our customers. And we think forward—staying curious, moving fast, and continuously learning. We believe meaningful work happens when people feel supported, heard, and empowered to contribute.

That’s why we think of ourselves as coworkers, not just employees—working together to solve complex challenges and deliver real impact for our customers and communities. As a full‑stack, full‑lifecycle technology partner, CDW brings deep expertise, strong relationships, and broad industry knowledge to help turn ideas into outcomes. When you join CDW, you become part of a collaborative environment where your work matters, your growth is supported, and your contributions help shape what’s next. Together, we deliver the full promise of what technology can do. Together, we Make Amazing Happen.

CDW is an equal opportunity employer. All qualified applicants will receive consideration for employment without regards to race, color, religion, sex, sexual orientation, gender identity, national origin, disability status, protected veteran status or any other basis prohibited by state and local law.      At CDW, we make technology work so people can do great things. We are a leading multi-brand technology solutions provider to business, government, education and healthcare customers in the United States, the United Kingdom and Canada.

Our coworkers across the globe are working together to bring technology to life for our customers by solving complicated IT business challenges, providing outstanding service, and orchestrating the technology landscape to optimize our customers’ performance.

Minimum requirements

  • Bachelor's degree or equivalent experience with 2+ years in proposal writing, management, project management, or technical/business writing.
  • Excellent writing, editing, verbal communication, and multitasking skills with strong attention to detail and compliance focus.
  • Proficiency in generative AI tools, Microsoft Office, Adobe Acrobat, and ability to work under pressure with sound judgment.

This listing was parsed by AI and may not be complete. Check the official posting on CDW's site for the most accurate information.

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