Proposal Manager - Remote

System One
Chicago, IL

Job Title: Proposal Manager
Location: Remote
Type: Contract - Part Time
Compensation: $48 - $61 hourly
Contractor Work Model: Remote
Hours: 10-30 hours per week

Proposal Manager

The client is looking for an amazingly talented Proposal Manager, to join our team! In this role you will get to champion the development and delivery of major proposals, qualifications, and other business development materials for pursuits within the critical infrastructure market, nation-wide.

What You'll Be Doing:
  • Leads and manages a team in the development of complex proposals to craft compliant, responsive, and compelling deliverables that solve customers’ problems and differentiates us from the competition.
  • Sets the overall strategy for proposal development and maintains a high degree of decision-making authority.
  • Holds team members accountable for their work and encourages them to stay focused and motivated throughout the process; provides timely feedback, celebrates milestones and achievements, and recognizes the contributions of each team member.
  • Provides strategic guidance and mentorship to team members, including capture teams.
  • Proactively manages stakeholder relationships and communicates proposal strategies and progress to senior leadership; contributes valuable insights and recommendations to improve overall efficiency and effectiveness of the proposal management function.
  • Addresses and resolves any issues or conflicts that may arise within the team, mediates disagreements, finds solutions to challenges, and maintains a positive working environment.
  • Refines and optimizes proposal processes and best practices to drive pursuit excellence.
  • Perform detailed analysis of RFP/RFQ/RFI documents to assess requirements and develop compelling proposal narratives that demonstrate our value proposition.
  • Builds compliance matrices, schedules, and annotated outlines.
  • Capture teams to guide proposal development efforts through the Business Acquisition Process (BAP).
  • SMEs to convey our winning narrative throughout the proposal.
  • Graphics and desktop publishing teams to develop tailored templates, infographic concepts, and standards for proposal look and feel, writing style, and layout.
  • Facilitates proposal kick-off meetings, milestone meetings, color reviews (e.g., pink, red, gold) and recovery periods to ensure quality deliverables.
  • Facilitates strategy-driven workshops (e.g., storyboarding, WinLabs, writer’s workshops) to produce compelling messaging and creative narratives for top pursuits.
  • Writes non-technical portions of the proposal (e.g., cover letters, executive summaries, project descriptions, resumes, team qualifications, management plans, and win themes and discriminators).
  • Reviews proposal drafts and final documents for compliance, responsiveness, thoroughness, accuracy, and quality.
  • Establishes a proposal schedule and resource plan to facilitate on-time delivery of all required documents.
  • Manages and oversees interview/oral preparation, development of collateral, and coaching activities.
  • Leads team initiatives to introduce and promote efficiencies and improve win rates across the business segment.
  • Collaborates with business development and regional leadership to develop collateral (e.g., fact sheets, leave behinds, client specific PowerPoint presentations) related to pre-positioning activities.
  • Collaborate with our graphics team to establish templates and standards for proposal look and feel, writing style, and layout
  • Responsible for writing non-technical portions of the proposal (i.e., cover letters, executive summaries, project descriptions, resumes, team qualifications, various management plans, win themes and discriminators, etc.)
  • Establish a production schedule and resource plan to ensure all required proposal documents are produced properly and delivered on time
  • Oversee client interview preparation, development of collateral and coaching activities
  • Contribute and maintain SalesCloud Opportunity CRM record for accuracy and completeness
  • Perform closeout activities ensuring lessons learned and debriefing process is initiated
What Required Skills You'll Bring:
  • Strong facilitation, leadership, and communication skills to lead capture teams through the pursuit lifecycle
  • Excellent written, interpersonal, and communication skills (ability to write executive summaries, cover letters and other non-technical sections)
  • Able to inspire outstanding work from team members with a range of experience and technical abilities in the development of proposal documents
  • Capable to adapting to changing priorities in a very dynamic work environment and demonstrate the ability to work in stressful situations with critical deadlines (evening and weekend work may be required to meet deadlines)
  • Required to work on multiple assignments, with overlapping schedules, and needs to be able to multi-task and delegate responsibilities to team members to accomplish all tasks
  • Ensure alignment with corporate strategy, business line strategic goals, promote technologies/innovation, build meaningful relationships, and align with business markets
  • Proficient in utilizing Adobe Creative Suite (Adobe In-Design, Illustrator, and Acrobat Pro)
  • Proficient in Microsoft Office Suite software (Word, Excel, and PowerPoint)
What Desired Skills You'll Bring:
  • Four-year degree in field of expertise (or equivalent)
  • Approximately 12+ years of progressive proposal management experience (or equivalent)
  • Professional registration, designation, or certification desired (e.g., Associate Proposal Management Professional (APMP), Project Management Professional, Shipley Associates)
  • AEC industry experience seven is highly preferred, particularly in the preparation and management of large program management proposals ($500M+) and/or proposals involving alternate project delivery (design-build/public private partnerships)

System One, and its subsidiaries including Joulé, ALTA IT Services, and Mountain Ltd., are leaders in delivering outsourced services and workforce solutions across North America. We help clients get work done more efficiently and economically, without compromising quality. System One not only serves as a valued partner for our clients, but we offer eligible employees health and welfare benefits coverage options including medical, dental, vision, spending accounts, life insurance, voluntary plans, as well as participation in a 401(k) plan.

System One is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, age, national origin, disability, family care or medical leave status, genetic information, veteran status, marital status, or any other characteristic protected by applicable federal, state, or local law.

#M-
#LI-
#DI-

Ref: #236-Eng Pasadena


System One, and its subsidiaries including Joulé, ALTA IT Services, TeamPeople, and Mountain Ltd., are leaders in delivering outsourced services and workforce solutions across North America. We help clients get work done more efficiently and economically, without compromising quality. System One not only serves as a valued partner for our clients, but we offer eligible employees health and welfare benefits coverage options including medical, dental, vision, spending accounts, life insurance, voluntary plans, as well as participation in a 401(k) plan.

System One is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, age, national origin, disability, family care or medical leave status, genetic information, veteran status, marital status, or any other characteristic protected by applicable federal, state, or local law.

Posted 2026-02-24

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