Top Tech Jobs & Startup Jobs in Chicago, IL

Leads and develops senior engineering teams delivering production AI solutions for tax, audit, and accounting clients. Owns hiring, staffing, capacity planning, client delivery, technical architecture, AI quality controls, risk mitigation, operating costs, and client outcomes. Oversees LLM applications using RAG, agents, integrations, evaluation frameworks, and observability. Partners with business, product, consulting, and platform leaders to improve engineering effectiveness, manage escalations, and align capacity with demand.

Build and deliver enterprise integrations connecting AI solutions with tax and audit products, ERP systems, document platforms, and data warehouses. Develop document-processing, retrieval, embedding, and vector-search pipelines; enable AI agents through APIs and MCP; and establish data validation and quality controls. Implement secure authentication, testing, monitoring, deployment patterns, and operational runbooks. Partner with clients and cross-functional engineering, platform, consulting, and reliability teams to deliver reusable, production-ready solutions.

Build and deploy reliable AI automations for tax and audit professionals. Responsibilities include understanding client workflows, designing controlled AI solutions, creating prompts and agents, developing prototypes with Python and low-code tools, validating accuracy through expert datasets and test harnesses, demonstrating solutions to clients, and collaborating with domain, editorial, product, and engineering teams. The role requires substantial tax or audit experience, professional judgment, and the ability to translate complex workflows into practical AI applications.

Manage assigned corporate SMB accounts through migration to CoCounsel, from outbound outreach and discovery through completed transition. Meet migration quotas, maintain Salesforce records, forecast progress, identify risks, negotiate terms, and coordinate with internal teams to resolve customer issues. Serve as a consultative advisor by mapping customer workflows to CoCounsel, demonstrating value, addressing objections, and capturing feedback. Requires B2B sales experience, quota attainment, account management, CRM proficiency, and strong communication skills.