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Proposal Writer Jobs in Chicago, IL (NOW HIRING)

Cengage Learning, Inc.

Proposal Writer

Chicago, IL · On-site

The Proposal Writer for our K-12 learning market is responsible for managing the Request for Proposal (RFP) process and will engage key internal partners to develop a proposal strategy that balances ...

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 ...

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 ...

Plantemoran

Proposal Manager

Chicago, IL · On-site

Working in a fast-paced and creative environment, we write and design business proposals and presentations to support the firm's business development and pursuit of new opportunities. We are seeking ...

Transdev

Proposal Director

Lombard, IL

$117K - $146K/yr

As the leader of a fast-paced proposal team, the Proposal Director ensures proposals reflect project strategy, are well written, compliant to the RFP, and reflect the Transdev brand. This position is ...

Transdev

Proposal Director

Lombard, IL · On-site

$117K - $146K/yr

As the leader of a fast-paced proposal team, the Proposal Director ensures proposals reflect project strategy, are well written, compliant to the RFP, and reflect the Transdev brand. This position is ...

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All JobsProposal Writer JobsProposal Writer Jobs in Chicago, IL

Proposal Writer information

See Chicago, IL salary details

$37.1K

$83.8K

$138.1K

How much do proposal writer jobs pay per year?

As of Sep 4, 2026, the average yearly pay for proposal writer in Chicago, IL is $83,764.00, according to ZipRecruiter salary data. Most workers in this role earn between $65,500.00 and $93,300.00 per year, depending on experience, location, and employer.

What is a proposal writer?

Proposal writers compose documents to gain support for a project, enter into a business agreement, or convince clients to buy products and services. To complete the proposal, they usually work with a team to research a specific issue, conduct interviews, collect information, and organize the data before submitting the application or sending the contract to a client. Proposal writers may work for non-profit organizations or private companies, or they may be freelancers who work for many different businesses. Some proposal writers specialize in a specific industry, such as grant writing for non-profit organizations.

What does a proposal writer do?

A Proposal Writer is responsible for creating documents that outline a company's products, services, or solutions in response to requests from clients or potential customers. Their main goal is to craft persuasive and clear proposals that showcase the value and benefits of their organization’s offerings, usually to secure new business or funding. Proposal Writers work closely with sales, marketing, and subject matter experts to gather information and tailor proposals to specific client needs. They must ensure proposals are compliant with client requirements and deadlines, and often manage multiple projects at once.

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 writing, research, and organizational skills, often supported by a degree in English, communications, or a related field. Familiarity with proposal management tools (such as RFPIO or Loopio), content management systems, and sometimes APMP certification is valuable. Strong attention to detail, collaboration, and the ability to work under deadlines are critical soft skills. These skills ensure persuasive, compliant proposals that meet client requirements and increase win rates in competitive bidding environments.

How does a proposal writer typically collaborate with subject matter experts and other team members during the proposal development process?

A Proposal Writer often works closely with subject matter experts (SMEs), project managers, and business development teams to gather the technical, financial, and strategic information required for compelling proposals. This collaboration usually involves conducting interviews, facilitating content reviews, and coordinating input from various stakeholders to ensure the proposal is accurate and tailored to client needs. Effective communication and strong organizational skills are crucial to managing multiple contributors, meeting tight deadlines, and producing high-quality submissions. This teamwork helps ensure that the proposal aligns with both client expectations and company objectives.

Are proposal writers in demand?

Proposal writers are in demand across various industries such as government, nonprofit, and private sectors, especially for organizations that regularly submit bids and grant applications. Strong writing skills, familiarity with proposal management tools, and the ability to meet strict deadlines are important for success in this role.

How much does a proposal writer make?

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 some may work freelance or on contract for different rates.
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Proposal Writer jobs near you
Infographic showing various Proposal Writer job openings in Chicago, IL as of August 2026, with employment types broken down into 100% Full Time. Highlights an 49% In-person, and 51% Remote job distribution, with an average salary of $83,764 per year, or $40.3 per hour.

Proposal Writer

Cengage Learning, Inc.

Chicago, IL • On-site

Full-time

Posted 23 days ago

Key responsibilities

  • Support all aspects of the RFP process from start to finish, including vetting, strategy calls, content collaboration, editing, and proposal preparation.

  • Analyze RFP bids to determine compliant response structure and format, and generate detailed response plans and schedules.

  • Partner with the Sales team to create innovative approaches and deliverables to differentiate proposals.

Job description

We believe in the power and joy of learning
At Cengage, our employees have a direct impact in helping learners around the world discover the power and joy of learning. We are bonded by our shared purpose - driving innovation that helps millions of learners improve their lives and achieve their dreams through education.
The Proposal Writer for our K-12 learning market is responsible for managing the Request for Proposal (RFP) process and will engage key internal partners to develop a proposal strategy that balances customer and channel priorities.
This role reports to the Manager, Sales Operations and Support whose team is responsible for the successful evaluation and execution of Cengage School RFP submission for districts and state departments of education. The successful candidate will support the effective project management of the bid process with on-time, high-quality responses by ensuring each proposal submission aligns with client need and represents Cengage's highest quality standards.
In this position, you will have the opportunity to contribute to a content library that clearly, concisely, and accurately articulates our proposed solution to the solicitation instructions and evaluation criteria. You will work alongside our sales, marketing, and product teams to audit and maintain a library of resources that contains up-to-date messaging and branding. In addition, you are encouraged to look for efficiencies to streamline and scale templates, processes, and systems.
What you'll do here:
  • Support all aspects of the RFP process from start to finish, including RFP vetting, strategy calls, content collaboration, editing, and proposal preparation.
  • Analyze RFP bid to determine compliant response structure and format.
  • Generate detailed response plans, schedules, and technical elements in the development of proposals in accordance with proposal specifications.
  • Delegate tasks to team members as appropriate.
  • Partner with the Sales team to create innovative approaches and deliverables to differentiate proposals to assure a winning first impression.
  • Identify gaps in the current RFP response model strategy, then propose new insights and secure support from internal partners to implement improvements within the processes, systems, and/or templates.
  • Track, evaluate, and improve RFP responses based on customer feedback, sales needs, and market research.
  • Complete other duties as assigned to meet company goals.

Skills you will need here:
  • A minimum of 2 years experience in proposal management with sales support or writing.
  • BA/BS in writing, communications, marketing, or related field.
  • Ability to serve as team mentor to coordinate proposal efforts simultaneously within tight timeframes.
  • Prior success in developing, implementing, and evaluating proposals that balance user needs with business requirements.
  • Strong interpersonal skills: the ability to empathize, support, and anticipate the needs of external customers and internal teammates/departments.
  • Excellent written and verbal communication with the ability to influence and align stakeholders while driving for results.
  • Able to remain agile while successfully project managing a high volume of work in a fast-paced, deadline-driven environment.
  • Understanding of emerging proposal trends, technologies, and integration strategies.
  • Provide value to each proposal being developed as a knowledgeable resource and strategic problem solver.
  • Proficient with MS Office suite and Adobe Suite

Preferred Skills/Knowledge/Experience:
  • Experience working within the K12 education industry.
  • Previous experience working with proposal management software (Responsive)

Cengage is committed to working with broad talent pools to attract and hire strong and most qualified individuals. Our job applicants are considered regardless of any classification protected by applicable federal, state, provincial or local laws.
Cengage is also committed to providing reasonable accommodations for qualified individuals with disabilities including during our job application process. If you are an applicant with a disability and require reasonable accommodation in our job application process, please contact us at accommodations.ta@cengage.com.
About Cengage
Cengage, a global education technology company serving millions of learners, provides affordable, quality digital products and services that equip students with the skills and competencies needed to be job ready. For more than 100 years, we have enabled the power and joy of learning with trusted, engaging content, and now, integrated digital platforms. We serve the higher education, workforce skills, secondary education, English language teaching and research markets worldwide. Through our scalable technology, including MindTap and Cengage Unlimited, we support all learners who seek to improve their lives and achieve their dreams through education.
Compensation
At Cengage Group, we take great pride in our commitment to providing a comprehensive and rewarding Total Rewards package designed to support and empower our employees. Click here to learn more about our Total Rewards Philosophy.
The full base pay range has been provided for this position. Individual base pay will vary based on work schedule, qualifications, experience, internal equity, and geographic location. Sales roles often incorporate a significant incentive compensation program beyond this base pay range.
$67,000.00 - $87,100.00 USD

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