Enterprise AI transformation lead (Central)

WRITER; Chicago (IL); Hybrid; USD 180,000 - 260,000; Full time

Benefits offered by this job

Generous PTO

Medical, dental, and vision coverage

Paid parental leave

Fertility and family planning support

Wellness stipend

Learning and development stipend

Company stock options and 401k

annual learning stipend

Stock options & 401k

Job summary

A leading AI enterprise in Chicago is seeking an AI Transformation Lead to partner with Fortune 100 clients. This role involves managing customer portfolios, driving value realization, and building trusted C-suite relationships. The ideal candidate has 5–9 years of experience in strategic account management, change management mastery, and exceptional communication skills. This is a hybrid position with competitive compensation and generous benefits.

Qualifications

• 5‑9 years in strategic account management or transformation consulting.
• Proven track record of building C‑suite relationships.
• Mastery of change management and strategic thinking.
• Active listening, curious mindset, and leadership.
• Background in management consulting or strategy advisory.
• Aligned with WRITER values: Connect, Challenge, Own.

Responsibilities

• Manage a portfolio of customers while leading ROI and value initiatives.
• Act as a strategic transformation partner for Fortune 50‑100 customers.
• Build and manage C‑suite relationships as a trusted advisor.
• Lead value realization and ROI analysis for business reviews.
• Orchestrate cross-functional programs with multiple stakeholders.
• Identify expansion opportunities with sales on cross-sell/upsell.
• Create decks and frameworks to scale transformation practices.

Skills

Strategic account management

Change management

Communication

Leadership

Curiosity

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, 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 (12 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.

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