Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and grow a data science team to design, prototype, and productionize NLP/LLM systems for legal content. Set AI strategy, build evaluation and monitoring, drive RAG/agentic solutions, collaborate cross-functionally, and ensure scalable, reliable deployment and responsible use of generative AI.

Leads and develops a North American PMO team while overseeing end-to-end project portfolio delivery. Responsibilities include resource assignment, portfolio health, financial performance, risk and escalation management, executive reporting, project governance, quality assurance, stakeholder alignment, and delivery process improvement. The role drives consistent use of PMO tools and methodologies, ensures accurate Adaptive Work data, and supports successful project closure and business outcomes.

Leads insurance carrier implementations involving APIs and system-to-system integrations for underwriting, rating, and risk assessment. Serves as the primary customer-facing technical consultant, managing requirements, stakeholders, risks, project delivery, training, presentations, configurations, connectivity, and issue resolution. Builds trusted advisor relationships and coordinates internal teams to ensure successful implementation and adoption.

Develops, licenses, and manages analytical tax, accounting, and legal content for professional customers. Responsibilities include researching tax law, legislation, regulations, and case law; writing and editing practical guidance; using generative AI to improve content workflows; recruiting authors and negotiating licensing agreements; and collaborating with editorial, product, technical, sales, and marketing teams. Requires a JD, CPA designation, significant accounting experience, and at least two years each of tax legal and accounting experience.

Generates new and expansion revenue for legal technology, DMS integrations, and API solutions within large law firms. Leads complex enterprise sales cycles, technical discovery, executive engagement, demonstrations, proposals, negotiations, forecasting, and quota delivery. Partners with client managers and cross-functional Product, Engineering, Security, Legal, Engagement, and Customer Success teams. Translates technical capabilities into business value and navigates information security, procurement, legal, and technical validation processes.

Provide deep technical product knowledge and demonstrations, respond to RFPs/RFIs and security questionnaires, build proofs of concept and sales enablement materials, run webinars and trainings, collaborate cross-functionally to solve customer problems and drive sales. Writing and public-speaking intensive; frequent client-facing demos and up to ~25-30% travel.

Partner with corporate legal departments to design and implement AI-driven workflows and LexisNexis solutions. Conduct demos, trainings, executive briefings, and workshops; advise on AI adoption and governance; identify expansion opportunities; collect client feedback and relay product recommendations. Travel frequently to support client engagements.

Lead end-to-end delivery of client programs, managing scope, schedule, budget, risks and stakeholder alignment. Coordinate cross-functional teams, gather and validate requirements, and drive PMO best practices to ensure successful client outcomes and continuous improvement.