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Proposal Writing Jobs in Chicago, IL (NOW HIRING)

Swoon Staffing

Bid Proposal Manager

Chicago, IL · Remote

$45/hr

Experience with Responsive.io and Salesforce (SFDC) . * Strong proposal writing, editing, and project management skills. * Experience using proposal management platforms such as Loopio or RFPIO

New

Sodexo

Proposal Manager

Chicago, IL · Remote

Write and edit executive summaries, cover letters, and core proposal content. * Ensure compliance with client requirements, regulatory standards, and brand guidelines. * Collaborate with sales ...

Sodexo

Proposal Manager

Chicago, IL · Remote

Write and edit executive summaries, cover letters, and core proposal content. * Ensure compliance with client requirements, regulatory standards, and brand guidelines. * Collaborate with sales ...

Eisneramper Llp

Proposal Manager

Chicago, IL · Hybrid

Strong Business Writing/AP style preferred * Professional services experience a plus * Extensive ... Prior proposal experience preferred. Experience responding to Government proposals a plus. * Good ...

Eisneramper Llp

Proposal Coordinator

Chicago, IL · Hybrid

Strong Business Writing/AP style preferred * Professional services experience a plus * Extensive ... Prior proposal experience preferred. Experience responding to Government proposals a plus. * Good ...

Lindsay & Brownell

Proposal Coordinator

Chicago, IL · Hybrid

Strong Business Writing/AP style preferred * Professional services experience a plus * Extensive ... Prior proposal experience preferred. Experience responding to Government proposals a plus. * Good ...

Lindsay & Brownell

Proposal Manager

Chicago, IL · Hybrid

Strong Business Writing/AP style preferred * Professional services experience a plus * Extensive ... Prior proposal experience preferred. Experience responding to Government proposals a plus. * Good ...

The LaSalle Group

Proposal & RFP Specialist

Chicago, IL · On-site

$70K - $80K/yr

Develop, write, edit and assemble polished, customer-focused proposal responses while ensuring compliance with all requirements * Coordinate proposal timelines and deliverables across Sales ...

Ripple

Proposal Specialist

Chicago, IL · On-site

Proposal Management & Execution * Coordinate, create, and deliver Requests for Proposals (RFPs ... Outstanding written and oral communication with demonstrated ability to develop clear, concise, and ...

Ripple

Proposal Specialist

Chicago, IL · On-site +1

Proposal Management & Execution * Coordinate, create, and deliver Requests for Proposals (RFPs ... Outstanding written and oral communication with demonstrated ability to develop clear, concise, and ...

National Express Corp

Proposal Specialist

Warrenville, IL · On-site

$85K - $95K/yr

We are currently seeking a Proposal Specialist based in Lisle area with hybrid in office/remote ... Excellent verbal and written communication skills. * Flexible attitude, a team-player and strong ...

Federal Signal

Proposal Coordinator

Crete, IL

$43K - $63K/yr

The appropriate candidate for this role will provide comprehensive support to the Proposal ... Excellent verbal and written communication skills. * Organized, professional, and self-motivated.

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All JobsProposal Writing JobsProposal Writing Jobs in Chicago, IL

Proposal Writing information

See Chicago, IL salary details

$37.1K

$83.7K

$138K

How much do proposal writing jobs pay per year?

As of Jul 30, 2026, the average yearly pay for proposal writing in Chicago, IL is $83,679.00, according to ZipRecruiter salary data. Most workers in this role earn between $65,400.00 and $93,200.00 per year, depending on experience, location, and employer.

Are proposal writers in demand?

Proposal writers are in demand across various industries such as government, non-profit, and private sectors, especially for organizations that rely on grant funding and contract bids. Strong writing skills, familiarity with proposal formats, and experience with deadlines increase employability in this field.

What are the key skills and qualifications needed to thrive as a Proposal Writer, and why are they important?

To thrive as a Proposal Writer, you need excellent written communication, research, and project management skills, often supported by a degree in English, communications, or a related field. Familiarity with proposal management software (like RFPIO or Qvidian), Microsoft Office Suite, and sometimes knowledge of compliance standards or certifications (such as APMP) is highly valued. Strong attention to detail, collaboration, and the ability to work under tight deadlines help set outstanding proposal writers apart. These skills ensure that proposals are compelling, compliant, and delivered on time, increasing the chances of winning business opportunities.

What is the difference between Proposal Writing vs Grant Writing?

AspectProposal WritingGrant Writing
Primary FocusCreating proposals for various projects, services, or business opportunitiesDeveloping grant applications to secure funding from organizations or government agencies
Required CredentialsWriting skills, understanding of client needs, industry knowledgeWriting skills, knowledge of grant processes, often familiarity with specific funding agencies
Work EnvironmentConsulting firms, corporate departments, freelanceNonprofits, research institutions, government agencies

Proposal Writing involves crafting proposals for a variety of projects or business opportunities, while Grant Writing specifically focuses on securing funding through grant applications. Both roles require strong writing skills, but Grant Writing often demands knowledge of funding sources and grant guidelines. Understanding these differences helps organizations find the right expertise for their needs.

How do you become a proposal writer?

To become a proposal writer, you typically need strong writing and research skills, a good understanding of the industry or organization, and experience with proposal development processes. Many proposal writers have a background in business, communications, or related fields, and may use tools like Microsoft Office or proposal management software. Gaining relevant experience through internships or entry-level positions can also help establish a career in proposal writing.

What are some common challenges faced by proposal writers, and how can they be effectively managed?

Proposal writers often face tight deadlines, managing input from multiple stakeholders, and ensuring proposals align with client requirements. Balancing thorough research with clear, persuasive writing can also be challenging, especially when dealing with complex or technical subjects. Effective organization, strong communication skills, and the use of proposal management tools can help streamline the process and improve collaboration, making it easier to produce high-quality, competitive proposals.

What is proposal writing?

Proposal writing is the process of creating documents that outline plans, solutions, or offerings for a specific project, grant, or business opportunity. These documents are typically submitted to organizations, clients, or funding bodies to persuade them to approve, fund, or support a particular idea or service. Effective proposal writing involves understanding the audience's needs, clearly presenting objectives and methods, and demonstrating value or potential impact. Proposal writers often follow specific formats or guidelines set by the recipient, ensuring all requirements are met and the proposal stands out among competitors.

How much do proposal writers get paid?

Proposal writers typically earn between $50,000 and $80,000 annually, depending on experience, industry, and location. Senior proposal writers or those with specialized skills can earn higher salaries, and freelance proposal writers may charge hourly or project-based rates. Strong writing, research, and proposal management skills are essential for higher pay in this role.

What are the three C's of proposal writing?

The three C's of proposal writing are clarity, conciseness, and completeness. These principles help proposal writers communicate their ideas effectively, ensuring the proposal is easy to understand, free of unnecessary information, and covers all required details. Mastering these aspects is essential for success in proposal writing roles.
What are popular job titles related to Proposal Writing jobs in Chicago, IL? For Proposal Writing jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Proposal Writing jobs in Chicago, IL look for? The top searched job categories for Proposal Writing jobs in Chicago, IL are:
Proposal Writing jobs near you
Infographic showing various Proposal Writing job openings in Chicago, IL as of July 2026, with employment types broken down into 92% Full Time, 4% Part Time, 2% Temporary, and 2% Contract. Highlights an 76% In-person, 10% Hybrid, and 14% Remote job distribution, with an average salary of $83,698 per year, or $40.2 per hour.

Bid Proposal Manager

Swoon Staffing

Chicago, IL • Remote

$45/hr

Contractor

Dental, Vision

Posted 3 days ago

New

Job description

Position: Bid Proposal Manager
Location: Remote
Pay Rate: $45/hr
Duration: 6-month contract (potential for extension and/or conversion)


In this role, you'll partner with the existing Bid Proposal Manager to lead the end-to-end proposal process for enterprise sales opportunities, ensuring high-quality, compliant, and competitive responses for RFPs, RFIs, and customer questionnaires.


Key Responsibilities:

  • Manage enterprise RFPs, RFIs, and proposal responses from intake through final submission.
  • Coordinate proposal timelines, kickoff meetings, and cross-functional contributors including Sales, Product, Legal, Finance, Security, Marketing, and Design.
  • Develop proposal strategies aligned with customer requirements and competitive positioning.
  • Ensure proposals are accurate, compliant, visually compelling, and delivered on time.
  • Collaborate with Sales and Business Development teams to create customized value propositions and strategic messaging.
  • Maintain and improve proposal templates, content libraries, and response documentation.
  • Track proposal progress, risks, and deliverables while managing multiple concurrent bids.
  • Support proposal process improvements, documentation, and onboarding of additional proposal resources as needed.


Qualifications:

  • Bachelor's degree required.
  • 5+ years of enterprise bid and proposal management experience (7+ years preferred).
  • Experience managing complex RFPs, RFIs, and customer questionnaires.
  • Experience with Responsive.io and Salesforce (SFDC).
  • Strong proposal writing, editing, and project management skills.
  • Experience using proposal management platforms such as Loopio or RFPIO.
  • Proficiency with Microsoft Office (Word, Excel, PowerPoint) and SharePoint.
  • Excellent organizational, communication, and stakeholder management skills.
  • Experience supporting B2B and government/federal proposals is a plus.
  • APMP or PMP certification is a plus.