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Senior Proposal Specialist

Job in Kankakee, Kankakee County, Illinois, 60901, USA
Listing for: CDW
Full Time position
Listed on 2026-10-26
Job specializations:
  • Business
    Regulatory Compliance Specialist, Business Administration
Job Description & How to Apply Below

Senior Proposal Specialist

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…
Position Requirements
10+ Years work experience
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