Senior Proposal Specialist

Location: Virtual - Illinois

The Senior Proposal Specialist is a seasoned proposal leader who owns the largest, most complex, high-value pursuits (RFPs, RFIs, RFQs and similar solicitations) from assignment through submission and post-submission. As the "quarterback" of each pursuit, the role coordinates all resources across sales, technical, pricing, contracts, legal, program management, partners and vendors with a high degree of independence.

An expert persuasive writer and disciplined project manager, the Senior Proposal Specialist uses the content library and company-approved generative AI tools to produce compliant, win-focused responses efficiently. The role also serves as a coach, mentor and process leader for the department, with the goal of increasing win rates and revenue.

What You Will Do

Opportunity Assessment & Planning

• Lead the largest, most complex and high-value pursuits, including multi-volume and high-dollar bids.
• Analyze requirements, evaluation criteria and risks; build compliance matrices mapping each to an owner.
• Research the customer, incumbent and competition, and inform sales-led bid/no-bid decisions.

Proposal Leadership & Project Management

• Run the kickoff, build the schedule backward from the due date, define roles and track risks and actions.
• Manage many concurrent proposals with little oversight; hold contributors accountable without authority.
• Serve as the escalation point for difficult pursuits and their schedule, resource and compliance issues.

Color Team Review Process

Lead Kickoff, Pink, Red, Gold and White reviews; coordinate Green (pricing), owned by sales or technical leads.

Drive reviewer comments to closure and serve as expert reviewer on other team members' pursuits.

Strategy, Win Themes & Writing

• Shape win strategy, themes, discriminators and value propositions with the opportunity team.
• Write executive summaries and advise sales leadership on win themes and proposal strength.
• Write persuasive, accurate, compliant content in one voice, aligned to evaluation criteria for easy scoring.

AI & Content Library

Use approved generative AI tools to analyze solicitations, draft and refine content and speed up reviews.

Verify AI output, protect confidential data, champion AI adoption and grow the content library.

Compliance, Production & Submission

Ensure compliance with forms, certifications and page limits; manage final assembly, QC and on-time submission.

Post-Submission Support

Lead debriefs and lessons-learned sessions and share findings with the team.

Play a stronger supporting role in clarifications, Q&A, orals, BAFOs, protests, award transition and close-out.

Coaching, Mentoring & Team Development

• Coach and mentor Proposal Specialists and junior staff, modeling best practices as a go-to expert.
• Have new hires shadow live pursuits; shadow junior members and review and edit their work.
• Support onboarding and training for new team members.

Department Initiatives & Process Improvement

• Lead or contribute to initiatives improving processes, templates, checklists, standards and the content library.
• Develop and deliver training; attend industry days, pre-proposal conferences and professional development.
• Analyze lessons learned and win/loss trends, recommend improvements and share best practices.

What We Expect of You

Minimum basic requirements

• Bachelor's degree or equivalent relevant work experience.
• Five or more years of proposal writing or proposal management experience, including leading complex responses.
• Excellent writing, editing and verbal communication skills, including strengthening others' work.
• Proven project management skills; able to lead large cross-functional teams without direct authority.
• Ability to manage multiple complex, deadline-driven projects at once with little oversight.
• Strong attention to detail and a focus on compliance.
• Proficiency with generative AI tools and the ability to help others adopt them.
• Advanced proficiency in Microsoft Office (Word, Excel, PowerPoint, Teams, SharePoint) and Adobe Acrobat.
• Sound judgment, composure under pressure and executive-level communication that influences senior leaders.
• Proven ability to coach and mentor others

Preferred skills, experience, and qualities needed

Public sector procurement expertise, including contracts, terms and conditions 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 (Practitioner or Professional) or PMI (PMP) certification.

Pay range: $90,000 - $126,200 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.