Top Tech Jobs & Startup Jobs in Chicago, IL

Leads AI/ML research and development, owning enterprise evaluation methodology, predictive and decision models, experimentation, causal inference, model economics, and production deployment. Builds evaluation suites and models hands-on, monitors performance and cost, prototypes agentic techniques, and guides AI-native engineering practices. The role also develops a small team, raises organizational ML fluency, supports data-as-a-service benchmarks, and communicates model uncertainty and business value to executives.

Administers employee benefits and leave programs, serves as a primary HR support contact, coordinates with vendors and payroll, processes HRIS transactions, manages leave and accommodation documentation, supports onboarding and offboarding, conducts audits and reconciliations, maintains confidential records, and ensures compliance with applicable benefits and employment regulations.

Design, develop, configure, test, integrate, document, and sustain MuleSoft API and integration capabilities. Build reusable API-led services, DataWeave transformations, secure connectivity, runtime policies, and CI/CD automation. Translate stakeholder and government requirements into maintainable solutions, troubleshoot complex platform and integration issues, support architecture and releases, and collaborate with cybersecurity, QA, infrastructure, operations, and business teams. Maintain technical documentation, test evidence, operational runbooks, and platform governance practices.

Design user experiences and interfaces for AI-driven and modern web applications. Create wireframes, user flows, mockups, and interactive prototypes in Figma; support digital signature workflows; maintain design systems and reusable components; collaborate with developers, product owners, and stakeholders; provide implementation guidance; and review completed work against approved designs in an Agile environment.

Manage federal and state tax compliance and consulting for startup clients, including corporate tax return reviews, filing deadlines, international tax work, financial statement support, client communication, and tax research. Maintain client records and projects in cloud-based systems, monitor support channels, collaborate with accounting, operations, sales, and marketing teams, and manage multiple client deadlines.

Own the enterprise sales cycle across a regional territory, from prospecting through negotiation and close. Develop account plans, build relationships with security, AI, and IT leaders, partner with marketing, SDRs, and sales engineering, deliver technical demonstrations, provide product feedback, represent the company at industry events, and meet revenue targets.

Loads, queries, validates, and analyzes data; refreshes databases; prepares client reports; identifies automation opportunities; supports UAT, system implementations, and quality assurance; and collaborates with cross-functional teams. The role requires database management, SQL, Oracle, Unix, Python, Power BI, data modeling, and relational database expertise, with opportunities to use scheduling and master data management tools.

Leads debt financing and structuring for joint venture projects, including feasibility analysis, financial modeling, credit agreement negotiation, loan portfolio management, refinancing, and capital strategy. Builds relationships with lenders and joint venture partners while communicating financing strategies and underwriting requirements. Manages multiple transactions, monitors debt markets, and provides guidance on capital obligations.

Generates sales pipeline for controlled substance businesses through account research, customized outreach, prospect discovery, qualification, and relationship management. Partners with growth, marketing, product marketing, and sales teams on messaging, segment strategy, account planning, and full-cycle sales support. Uses Salesforce and AI-enabled sales tools to improve prospecting, automate workflows, manage interactions, and drive qualified meetings and revenue growth.

Own go-to-market strategy for PandaDoc’s workflow product pillar. Responsibilities include customer research, positioning and messaging, AI narrative development, product and R&D partnership, launch planning, sales enablement, adoption campaigns, and expansion initiatives. The role sets success metrics and kill criteria, validates outcomes with data, and translates workflow automation and AI capabilities into clear customer value for business users and operators.