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Writing Assistant Jobs in Chicago, IL (NOW HIRING)

Wing Assistant

Sales Enablement Trainer

Chicago, IL · On-site +1

$29K - $35K/yr

Wing Assistant is hiring a hands on Sales Enablement Trainer to level up our sales team - not with ... Write sales copy that converts and can explain why it works. * Are comfortable on camera and can ...

Cna

Legal Secretary

Chicago, IL · Hybrid

$35K - $65K/yr

At CNA, we strive to create a culture in which people know they matter and are part of something ... Excellent written and verbal communication skills including professional phone etiquette and the ...

Cna

Billing & Collections Coordinator

Chicago, IL · Hybrid

$35K - $65K/yr

At CNA, we strive to create a culture in which people know they matter and are part of something ... Provides responses in writing and/or by telephone within designated call and transaction parameters.

CNA

AI Security Consulting Director

Chicago, IL · On-site

$97K - $189K/yr

At CNA, we strive to create a culture in which people know they matter and are part of something ... Write and maintain technology evaluation criteria for RFIs and RFPs covering AI security tooling ...

Wing Assistant

Sales Development Representative

Chicago, IL · On-site

$40K - $50K/yr

Confidence on the phone and in writing you can articulate value whether it's a 30-second cold call ... These tools assist our recruitment team but do not replace human judgment. Final hiring decisions ...

Cna

Corporate Paralegal

Chicago, IL · Hybrid

$47K - $78K/yr

At CNA, we strive to create a culture in which people know they matter and are part of something ... Excellent written and verbal communication skills including professional phone etiquette. Education ...

Cna

AI Security Consulting Director

Chicago, IL · Hybrid

$97K - $189K/yr

At CNA, we strive to create a culture in which people know they matter and are part of something ... Write andmaintaintechnology evaluation criteria for RFIs and RFPs covering AI security tooling and ...

Luxe Media, LLC

Speech Writer Volunteer

Chicago, IL · On-site

Editing, writing, and contributing to the strengthening of our communications through multiple ... Recommend visual aids that will assist in speeches/presentations when needed. Set standards for a ...

Hasana, Inc.

Speech Writer Volunteer

Chicago, IL

Editing, writing, and contributing to the strengthening of our communications through multiple ... Recommend visual aids that will assist in speeches/presentations when needed. Set standards for a ...

CNA

Corporate Paralegal

Chicago, IL · On-site

$47K - $78K/yr

At CNA, we strive to create a culture in which people know they matter and are part of something ... Excellent written and verbal communication skills including professional phone etiquette. Education ...

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All JobsWriting JobsWriting Assistant JobsWriting Assistant Jobs in Chicago, IL

Writing Assistant information

See Chicago, IL salary details

$15

$30

$82

How much do writing assistant jobs pay per hour?

As of Aug 14, 2026, the average hourly pay for writing assistant in Chicago, IL is $30.60, according to ZipRecruiter salary data. Most workers in this role earn between $17.27 and $23.44 per hour, depending on experience, location, and employer.

What do writing assistants make?

Writing assistants typically earn an average salary ranging from $30,000 to $60,000 per year, depending on experience, location, and employer. They often work in educational, corporate, or freelance settings and may use tools like word processors and editing software to support their tasks.

What jobs can I do if I like writing?

A writing assistant can pursue jobs such as content writer, copywriter, technical writer, editor, or blogger. These roles involve creating, editing, and proofreading written content across various industries and often require strong language skills and familiarity with writing tools like word processors or content management systems.

What is the difference between Writing Assistant vs Content Writer?

AspectWriting AssistantContent Writer
CredentialsTypically no formal degree required; strong writing skillsUsually holds a degree in English, Journalism, or related fields
Work EnvironmentOften works in educational, corporate, or editing settingsPrimarily works in marketing, media, or online publishing
Employer & Industry UsageUsed by educational institutions, editing agencies, and corporationsEmployed by media companies, marketing agencies, and online platforms
Search & Comparison IntentPeople compare to understand support roles in writing and editingPeople compare to find professional writing roles in content creation

The main difference is that a Writing Assistant primarily supports editing, proofreading, and improving existing content, often in educational or corporate settings. In contrast, a Content Writer focuses on creating original content for marketing, websites, or media. Both roles require strong writing skills, but their responsibilities and work environments differ significantly.

What is a writing assistant?

Writing assistants are professionals or software tools that help individuals improve their writing by providing support with grammar, structure, clarity, and style. They may review documents, suggest edits, or assist with brainstorming and organizing ideas. Writing assistants are commonly used by students, professionals, and anyone looking to enhance the quality of their written work. In workplaces and academic settings, they can play a key role in ensuring communication is clear and effective.

How does a writing assistant typically collaborate with editors and other team members?

As a Writing Assistant, you will frequently collaborate with editors, senior writers, and designers to support the production of high-quality content. This often involves revising drafts based on editorial feedback, researching topics to provide background information, and ensuring consistency in style and tone across projects. Clear communication and adaptability are essential, as you may need to juggle multiple assignments while meeting tight deadlines. Working closely with others not only sharpens your writing skills but also provides valuable insight into the editorial process.

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

To thrive as a Writing Assistant, you need strong writing, editing, and research skills, typically supported by a degree in English, communications, or a related field. Familiarity with word processing software, style guides (such as APA or MLA), and content management systems is often required. Attention to detail, time management, and the ability to collaborate effectively are standout soft skills in this role. These competencies ensure high-quality written materials, efficient workflow, and the ability to support writers and editors in meeting deadlines.

What are the most commonly searched types of Writing jobs in Chicago, IL?

The most popular types of Writing jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Writing Assistant jobs?

Cities near Chicago, IL with the most Writing Assistant job openings:

Writing Assistant jobs near you
Infographic showing various Writing Assistant job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 75% Full Time, 21% Part Time, 1% Temporary, and 2% Contract. Highlights an 98% Physical, 1% Hybrid, and 1% Remote job distribution, with an average salary of $63,646 per year, or $30.6 per hour.

Sales Enablement Trainer

Wing Assistant

Chicago, IL • On-site, Remote

$29K - $35K/yr

Full-time

Re-posted 23 days ago

Job description

Wing Assistant is hiring a hands on Sales Enablement Trainer to level up our sales team - not with generic intro decks, but by improving the actual emails, calls, and cadences our reps use every day. This is a coach who has carried a quota and closed, and uses that credibility to make real, measurable improvements on the floor.
If your first instinct when a deal stalls is "let me see the thread and the call recording" - read on.
Responsibilities
  • Sit in the calls - live and recorded - and find exactly where deals are being lost.
  • Rewrite the copy, scripts, and sequences that aren't converting, and prove the new version works.
  • A/B test sales emails, call openers, demo pitches, and tactics like personalized video - keep the winners, kill the losers.
  • Build and tune outbound cadences so reps follow up at the right time, on the right channel, with the right message.
  • Coach reps one-on-one on real calls and build the objection-handling playbook for our market - then drill it until it's reflexive.
  • Produce a video training series and self-serve modules with assessments, so new reps ramp fast and tenured reps keep sharpening.

Requirements
You'll thrive here if you
  • Have personally sold and closed - ideally outbound/high-volume B2B - and can show your numbers.
  • Write sales copy that converts and can explain why it works.
  • Are comfortable on camera and can produce clean training videos without a production team.
  • Can structure an A/B test, read the result honestly, and make the call.
  • Coach without crushing - you leave reps better and more confident.
  • Move fast: a diagnosis becomes a usable fix in hours, not weeks.
  • Know your way around a CRM (Hubspot plus) and a sales sequencing tool.

Nice to have
Experience in virtual staffing, BPO, or managed services • Pipedrive or CRM automations • video editing • sequencing tools (Apollo, Outreach, Salesloft, Instantly, Smartlead) • prior sales enablement assets (playbooks, battle cards, certification programs).
Why the Role
How the role actually runs - fast loop, not slow decks: Listen - Diagnose - Build - Intervene.
  • You hear the calls, name the specific problem, build the fix the same day, and get it into reps' hands immediately. A pattern that shows up Monday should have a tested correction in motion by midweek.

Why this role
  • You're joining at a build moment. You'll start lean and resourceful - and as the program proves it drives revenue, it ears more investment and room to grow. This is a roll-up-your-sleeves, multi-hat seat for someone who wants to own the engine, not manage a slide deck.

$29,000 - $35,000 a year
We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

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