Senior Proposal Specialist

This is a fully remote position, open to applicants in Illinois.

📋 Description

• Oversee the largest, most intricate, and high-value pursuits, including multi-volume and significant bids, from the initial assignment to submission and post-submission activities.

• Evaluate requirements, assessment criteria, and potential risks; create compliance matrices that assign ownership for each element.

• Conduct research on customers, incumbents, and competitors to guide sales-led bid/no-bid decisions.

• Facilitate kick-off meetings, develop schedules, define roles, and monitor risks and action items.

• Manage multiple proposals simultaneously with minimal supervision and hold contributors accountable without direct authority.

• Direct Pink, Red, Gold, and White color team reviews and oversee Green pricing evaluations.

• Develop win strategies, themes, differentiators, and value propositions.

• Compose executive summaries and compelling, accurate, compliant content that aligns with evaluation criteria.

• Utilize approved generative AI tools to analyze solicitations, draft and refine content, validate outputs, safeguard confidential information, and enhance the content library.

• Ensure adherence to forms, certifications, and page limits; oversee final assembly, quality assurance, and timely submission.

• Lead debriefs and lessons-learned sessions; assist with clarifications, Q&A, oral presentations, BAFOs, protests, award transition, and close-out processes.

• Mentor and coach Proposal Specialists and junior staff; assist with onboarding and training initiatives.

• Lead or contribute to the enhancement of processes, templates, checklists, standards, and the content library.

• Analyze lessons learned and win/loss trends, propose improvements, and share best practices.

⛳️ Requirements

• A Bachelor's degree or equivalent relevant work experience.

• At least five years of experience in proposal writing or management, including leading complex responses.

• Exceptional writing, editing, and verbal communication skills, including the ability to enhance others' work.

• Demonstrated project management capabilities; able to lead large, cross-functional teams without direct authority.

• Proficient in managing multiple complex, deadline-driven projects simultaneously with limited oversight.

• Strong attention to detail and a commitment to compliance.

• Familiarity with generative AI tools and the capability to assist others in their adoption.

• Advanced skills in Microsoft Office (Word, Excel, PowerPoint, Teams, SharePoint) and Adobe Acrobat.

• Sound judgment, poise under pressure, and executive-level communication that effectively influences senior leaders.

• Proven track record in coaching and mentoring others.

• Expertise in public sector procurement, including contracts, terms and conditions, and purchasing requirements.

• General understanding 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.

🏝️ Benefits

• Annual bonus target of 5% subject to the terms and conditions of the plan.

• Benefits package detailed at https://cdw.benefit-info.com/.

• Opportunities for coaching, mentoring, onboarding, training, professional development, and participation in industry events.

• An equitable, transparent, and respectful hiring process.