Training Writer Jobs in Chicago, IL (NOW HIRING)

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

WRITER is looking for a customer success professional who will own deployment and activation success across a customer portfolio. You'll embed deeply into your customers' organizations, understand their business objectives, and build the programs, communities, and frameworks that turn AI investment into measurable outcomes. You'll partner closely with a Transformation lead to identify the right WRITER capabilities for each use case, then design and execute the strategies that drive meaningful adoption: building champion networks, running customized workshops, and advising customers on how to scale their AI programs over time.

The ideal candidate brings a builder's mindset to customer success: you're not waiting for customers to engage, you're creating the conditions for it.

This is a hybrid role based in our Chicago and Austin hubs.

What you'll do

Own activation and platform success

• Deeply understand each customer's specific use cases, business objectives, and success metrics

• Build and co-develop custom AI solutions with customers, translating their specific use cases into workflows that drive measurable business impact

• Design and execute activation strategies that drive measurable platform adoption and business outcomes

• Implement champion programs, office hours, usage dashboards, customized trainings, and workshops

Build champion communities

• Create advocate networks and champion communities within customer organizations

• Establish power user communities that drive peer-to-peer learning

• Train internal customer trainers to scale enablement

• Design innovative customer experiences that deepen engagement

Lead educational workshops & live events

• Facilitate dynamic live and virtual training sessions tailored to diverse audiences

• Partner with curriculum team while owning customization and delivery for your customers

• Create memorable learning experiences that inspire action and drive adoption

Continuously improve & collaborate

• Refine materials based on customer feedback and adoption data

• Work cross-functionally to understand evolving customer needs

• Identify gaps and champion new training opportunities

• Build deep relationships with customer stakeholders and executive sponsors

What you need

Customer success & activation expertise

• At least 5 years of proven track record owning activation success and driving measurable adoption outcomes

• Deep experience understanding customer use cases: you discover, map, and leverage specific workflows and business objectives

• Experience implementing activation strategies: champion programs, office hours, dashboards, and workshops

• Success building advocate networks and power user communities

• Ability to connect platform usage to business outcomes and articulate ROI

AI & technical proficiency

• Ability to scope, design, and deliver custom solutions and demos tailored to customer use cases, working hands-on alongside business stakeholders

• Comfortable understanding technical concepts and communicating them effectively to varied audiences

• Ability to demonstrate use cases and articulate business value

Facilitation & education skills

• Expertise delivering virtual and live instructor‑led workshops

• Skilled at tailoring content and delivery to diverse audiences based on their use cases

• Ability to partner effectively with curriculum teams while owning customization and delivery

Collaboration & growth

• Excellence building relationships with stakeholders at all levels

• Strong program management skills and natural advisor mindset

• Thrive in fast‑paced environments; comfortable with experimentation

• Self-aware, feedback‑driven, and committed to continuous growth

Travel Requirements: 25% domestic and international travel may be required.

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:

  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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