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Flexible Development Writer Jobs in Illinois (NOW HIRING)

WRITER

AI deployment engineer (Central)

Chicago, IL · On-site

$100 - $125/hr

About WRITER WRITER is where the world's leading enterprises orchestrate AI-powered work. Our ... Flexible spending account and dependent FSA options * Health savings account for eligible plans ...

Writer

Solutions architect (Central)

Chicago, IL · On-site

$164K - $245K/yr

About WRITER WRITER is where the world's leading enterprises orchestrate AI-powered work. Our ... Lead the development and execution of compelling proofs of concept (PoCs) and demonstrations ...

Writer

AI deployment engineer (Central)

Chicago, IL · On-site

$131K - $166K/yr

About WRITER WRITER is where the world's leading enterprises orchestrate AI-powered work. Our ... Flexible spending account and dependent FSA options * Health savings account for eligible plans ...

Writer

Strategic account executive (Central)

Chicago, IL · On-site

$340K - $350K/yr

About WRITER WRITER is where the world's leading enterprises orchestrate AI-powered work. Our ... Flexible spending account and dependent FSA options * Health savings account for eligible plans ...

iMentor

Corporate Development Manager

Chicago, IL · On-site

$60 - $80/hr

Development Writing (50%) * Support 3 frontline fundraisers to write proposals and grant reports ... Flexible and adaptive to effectively manage changing priorities and new opportunities. * Salesforce ...

Meineke - 2275

Service Writer

South Elgin, IL · On-site

$17 - $25/hr

Flexible schedule * Paid time off Benefits/Perks * Competitive Compensation * Career Advancement ... Training and Development * Comprehensive Benefits Package * Employee Discounts * Positive Work ...

Endeavor Health

Philanthropy Writer

Evanston, IL

$30.46 - $45.69/hr

Gift Proposal and Case Development: Lead theend-to-end project management and creationof major gift ... Must be flexible and adaptable to changing priorities and proactively address challenges in a fast ...

Meineke - 2275

Service Writer

South Elgin, IL · On-site

Benefits: Competitive salary Flexible schedule Paid time off Benefits/Perks Competitive ... Training and Development Comprehensive Benefits Package Employee Discounts Positive Work ...

VSA Partners

Senior Writer

Chicago, IL · On-site

Collaborate in the development and definition of the "voice" for a client, a program or individual ... Flexible Time Off Policy * Paid holidays, including agency soft closing Christmas Eve-New Year ...

NorthShore

Philanthropy Writer

Evanston, IL · On-site

$30.46 - $45.69/hr

Gift Proposal and Case Development: Lead the end-to-end project management and creation of major ... Must be flexible and adaptable to changing priorities and proactively address challenges in a fast ...

writer.com

Solutions architect (Central)

Chicago, IL · On-site

$150 - $200/hr

About WRITER WRITER is where the world's leading enterprises orchestrate AI-powered work. Our ... Lead the development and execution of compelling proofs of concept (PoCs) and demonstrations ...

Meineke

Service Writer

South Elgin, IL · On-site

$17 - $25/hr

Flexible schedule * Paid time off Benefits/Perks * Competitive Compensation * Career Advancement ... Training and Development * Comprehensive Benefits Package * Employee Discounts * Positive Work ...

Endeavor Health

Philanthropy Writer

Warrenville, IL

$30.46 - $45.69/hr

Gift Proposal and Case Development: Lead theend-to-end project management and creationof major gift ... Must be flexible and adaptable to changing priorities and proactively address challenges in a fast ...

Meineke

Service Writer

South Elgin, IL · On-site

$17 - $25/hr

Flexible schedule * Paid time off Benefits/Perks * Competitive Compensation * Career Advancement ... Training and Development * Comprehensive Benefits Package * Employee Discounts * Positive Work ...

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Infographic showing various Flexible Development Writer job openings in Illinois as of August 2026, with employment types broken down into 1% As Needed, 78% Full Time, 19% Part Time, and 2% Contract. Highlights an 86% Physical, 3% Hybrid, and 11% Remote job distribution.

Enterprise AI transformation lead (Central)

Writer

Chicago, IL • On-site

$156K - $198K/yr

Full-time

Medical, Dental, Vision, Retirement, PTO

Re-posted 11 days ago

Key responsibilities

  • Manage a portfolio of customers and lead ROI and value initiatives in partnership with a customer success manager.

  • Act as a strategic transformation partner for Fortune 50-100 customers by setting vision and defining frameworks to drive AI adoption.

  • Build and manage C-suite relationships as a trusted advisor to prioritize AI initiatives and facilitate value realization.

Job description

About WRITER
WRITER is where the world's leading enterprises orchestrate AI-powered work. Our vision is to expand human capacity through superintelligence. And we're proving it's possible - through powerful, trustworthy AI that unites IT and business teams together to unlock enterprise-wide transformation. With WRITER's end-to-end platform, hundreds of companies like Mars, Marriott, Uber, and Vanguard are building and deploying AI agents that are grounded in their company's data and fueled by WRITER's enterprise-grade LLMs. Valued at $1.9B and backed by industry-leading investors including Premji Invest, Radical Ventures, and ICONIQ Growth, WRITER is rapidly cementing its position as the leader in enterprise generative AI.
Founded in 2020 with office hubs in San Francisco, New York City, Seattle, Austin, Chicago, and London, our team thinks big and moves fast, and we're looking for smart, hardworking builders and scalers to join us on our journey to create a better future of work with AI.
About the role
We are looking for a visionary and execution-oriented AI transformation lead to serve as a high-impact partner for our most strategic Fortune 100 accounts. In this role, you'll be the architect of change, moving beyond simple software implementation to help the world's largest organizations fundamentally rethink how they work. You'll sit at the intersection of business strategy and cutting-edge technology, translating the power of the WRITER platform into measurable P&L impact and helping executives navigate the shift to an AI-first operating model.
This is a rare opportunity to build the playbook for enterprise AI transformation. You won't just be managing accounts; you'll be driving the next industrial revolution by helping C-suite leaders move from AI experimentation to full-scale value realization. Your work will directly influence WRITER's product roadmap and help define how the world's biggest brands use superintelligence to expand human capacity.
This role is available as a hybrid position based out of our Chicago and Austin hubs. You will report to the director of AI transformation and success.
What you'll do
  • Manage a portfolio of customers while leading ROI and value initiatives in partnership with a customer success manager who focuses on the adoption strategy
  • Act as a strategic transformation partner for Fortune 50-100 customers by setting vision and defining the JTBD framework with leadership teams to drive AI adoption
  • Build and manage C-suite relationships as a trusted advisor to make AI a top priority for executives
  • Lead value realization and ROI delivery by conducting analysis through surveys and interviews to frame the P&L impact of AI adoption in business reviews
  • Orchestrate complex cross-functional programs across multiple stakeholders while managing customer teams, escalations, risk mitigation, and program updates
  • Proactively identify and drive expansion opportunities by anticipating customer needs and working with sales on cross-sell and upsell initiatives
  • Scale transformation best practices by producing and "processifying" decks, frameworks, and communications for the wider team

☆ What you need
  • 5-9 years in strategic account management or transformation consulting for Fortune 50-100 companies with a proven track record of building C-suite relationships and leading large-scale transformations
  • Mastery of change management and strategic thinking with the ability to set vision, define frameworks, and translate capabilities to measurable outcomes and P&L impact
  • Exceptional executive presence and communication skills used to lead composed presentations to boards while proactively orchestrating cross-functional teams and resolving conflicts
  • A curious mindset and an active listening style that marks you as a genuine leader who people want to follow
  • A strong professional background in management consulting or strategy advisory which will help you navigate our customers' complex business environments
  • An intrinsic motivation to do your best work while remaining deeply aligned with our core values to Connect, Challenge, and Own

Benefits & perks (US Full-time employees)
  • Generous PTO, plus company holidays
  • Medical, dental, and vision coverage for you and your family
  • Paid parental leave for all parents (16 weeks)
  • Fertility and family planning support
  • Early-detection cancer testing through Galleri
  • Flexible spending account and dependent FSA options
  • Health savings account for eligible plans with company contribution
  • Annual work-life stipends for:
    • Wellness stipend for gym, massage/chiropractor, personal training, etc.
    • Learning and development stipend
  • Company-wide off-sites and team off-sites
  • Competitive compensation, company stock options and 401k

WRITER is an equal-opportunity employer and is committed to diversity. We don't make hiring or employment decisions based on race, color, religion, creed, gender, national origin, age, disability, veteran status, marital status, pregnancy, sex, gender expression or identity, sexual orientation, citizenship, or any other basis protected by applicable local, state or federal law. Under the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.
By submitting your application on the application page, you acknowledge and agree to WRITER's Global Candidate Privacy Notice.

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