Top Tech Jobs & Startup Jobs in Chicago, IL

Lead AI transformation initiatives for Fortune 50–100 customers, partnering with executives to define adoption strategies, realize ROI, and quantify P&L impact. Manage strategic customer portfolios, C-suite relationships, cross-functional programs, escalations, and expansion opportunities. Develop transformation frameworks, decks, communications, and best practices while influencing product strategy. The role requires strategic account management or transformation consulting experience, executive presence, change-management expertise, and experience leading large-scale enterprise transformations.

Lead AI transformation initiatives for Fortune 50–100 customers, serving as a strategic partner to executives. Manage customer portfolios, define AI adoption visions and frameworks, deliver ROI and P&L impact analysis, build C-suite relationships, orchestrate cross-functional programs, resolve risks, support expansion opportunities, and develop scalable transformation playbooks and communications.

Negotiate SaaS licensing, partnership, data processing, supplier, and other commercial agreements. Develop contract templates and negotiation playbooks, improve sales contracting processes, advise and train go-to-market teams, and create scalable legal operations. Partner closely with sales, procurement, and sales operations while supporting enterprise customers and strategic partners in regulated industries.

Architects enterprise generative AI solutions for Fortune 500 prospects and customers. Leads technical discovery, proofs of concept, demonstrations, API integrations, and custom applications using WRITER’s platform. Advises executive and technical stakeholders on AI strategy and architecture roadmaps, partners with product and engineering teams, and drives platform adoption. The role requires strong customer-facing communication, enterprise architecture expertise, Python and API experience, and deep knowledge of LLMs and prompt engineering.

Partner with Fortune 500 customers to identify AI use cases, architect and implement custom applications, templates, and integrations, and guide enterprise adoption. The role uses Python, APIs, generative AI, and Knowledge Graph capabilities while translating complex technical concepts for business and executive audiences. It also develops scalable integration processes, documentation, and workflows; provides customer feedback to Product and Engineering; and drives successful outcomes and expansion within strategic accounts.

Generate outbound pipeline from target enterprise accounts, research prospects, develop value hypotheses, execute multi-touch account-based campaigns, qualify leads, and set meetings for sales teams. Maintain accurate Salesforce data and improve sales development processes through experimentation and automation. Partner with Account Executives, Marketing, and Sales while engaging Fortune 500 buyers about enterprise AI solutions.

Own the global sales enablement strategy for Account Executive and Sales Development Representative teams. Define sales methodology, deliver onboarding and ongoing training, manage certification and everboarding programs, maintain sales content, measure enablement effectiveness, and improve ramp time, win rates, quota attainment, and pipeline velocity. Partner with Sales leadership, Product Marketing, and RevOps while using AI-native workflows to improve seller productivity.

Drive net-new enterprise revenue for WRITER’s AI agent platform by managing the full sales cycle, prospecting strategic accounts, developing opportunities, leading executive discussions and negotiations, and owning a sales territory. The role requires consultative SaaS selling, accurate pipeline forecasting, cross-functional collaboration, and guiding customers through product adoption and deployment.

Own WRITER’s lifecycle and email marketing program from strategy through execution, including segmentation, personalization, nurture workflows, triggered journeys, testing, reporting, and optimization in HubSpot. Partner with demand generation, ABM, content, product marketing, and sales to support enterprise buying journeys and pipeline growth. Use behavioral, account, intent, and engagement signals to improve audience experiences, measure revenue impact, and explore AI-driven lifecycle marketing.

Own and evolve WRITER’s design system across design and engineering. Build production-quality React interfaces, reusable components, animations, and polished interactions while maintaining accessibility and consistency. Architect design-system primitives, synchronize Figma, documentation, and Storybook, improve design-to-code workflows, and drive adoption across the organization. Partner with designers, product managers, and engineers on AI product surfaces, including tool-call interfaces, streaming responses, agent states, and dynamic rendering.