Top Tech Jobs & Startup Jobs in Chicago, IL

Lead the engineering department, develop and empower engineers, establish systems and guardrails for reliable delivery, improve workflows, maintain technical involvement, and set metrics that drive productivity and impact. The role partners closely with Product, supports high-impact decisions, and builds a culture of trust, psychological safety, ownership, and clear communication.

Lead and develop a team of product managers while owning strategy, execution, and commercial performance for a portfolio of B2B data feeds. Directly manage a strategic data product, guide customer discovery, prioritize investments, partner with Data, Engineering, Quant Research, and commercial teams, and improve data quality, integration, onboarding, adoption, retention, and revenue outcomes.

Own end-to-end US payroll for 500+ employees, including multi-state compliance, tax requirements, benefits deductions, invoice reconciliation, and self-insured plan activity. Partner with Finance, People Ops, ADP, and benefits vendors to resolve discrepancies, support audits, W-2 preparation, open enrollment, and reconciliations. Maintain controls, documentation, and recurring processes while identifying opportunities to automate and scale payroll and benefits operations.

Lead the technical direction, architecture, and development quality of complex Android applications. Mentor engineers, integrate backend services, support offline-first functionality and diverse hardware, oversee CI/CD and releases, and document engineering standards. The role also involves robotics integrations for public safety use cases, including drones and body-worn cameras, while collaborating with technical and non-technical stakeholders.

Supports financial modeling, forecasting, budgeting, and monthly, quarterly, and annual reporting. Tracks SaaS metrics, validates data, identifies reporting inconsistencies, and provides ad hoc financial analysis to cross-functional teams. Contributes to go-to-market analysis, annual planning, growth strategies, and long-range planning while using AI tools to improve analytical efficiency.

Supports the SaaS order-to-cash and revenue lifecycle, including sales order processing, contract review, billing, invoicing, collections, revenue recognition, reconciliations, and month-end close. The role partners with Sales, Customer Success, and Finance to resolve account issues, maintain accurate billing data, support audits and internal controls, and improve billing processes.

Analyzes customer delivery, order fulfillment, inventory, replenishment, and logistics performance using analytics, AI tools, dashboards, and supply chain systems. Identifies root causes, service risks, and process improvements; supports exception management, forecasting, transportation optimization, and sales and operations alignment. Develops reports and SKU-level recommendations, collaborates with Sales, Planning, Distribution, and Transportation teams, and presents data-driven solutions to improve service, cost, inventory health, and operational efficiency.

Drives Listerine digital commerce initiatives across retail and social commerce platforms. Responsibilities include developing and optimizing product detail page content, monitoring sales and conversion performance, improving retail media programs, leading A/B tests, managing ratings and reviews, and supporting assortment, pricing, promotions, and content planning. The role collaborates with brand, customer development, media, legal, regulatory, R&D, creative agencies, and other partners to increase traffic, conversion, basket size, and sales.

Design, build, and ship AI-powered observability features using LLMs and agentic workflows. Rapidly prototype, iterate with real users, integrate AI into alerting, runbooks, and developer workflows, and ensure solutions are scalable, maintainable, and production-ready while collaborating cross-functionally.

Build full-stack Real User Monitoring features across frontend applications, backend services, APIs, and analytical storage systems. Design high-throughput telemetry ingestion, storage, querying, data models, and indexing strategies. Develop data-heavy user interfaces, optimize performance and costs, collaborate with SDK and cross-functional teams, and own projects from design through deployment, monitoring, testing, and iteration.

Leads complex healthcare technology and capital equipment implementations from initiation through completion. Coordinates clinical, technical, sales, customer, and hospital stakeholders; develops project plans and work breakdown structures; manages scope, risks, changes, communications, resources, and timelines; and ensures statement-of-work compliance and strong customer outcomes. This field-based role requires up to 75% travel across Arizona, New Mexico, Texas, and California.

Own and execute 1mind’s integrated marketing engine across demand generation, content, social, communications, customer marketing, and advocacy. Manage the marketing budget, track pipeline and channel ROI, run full-funnel campaigns, produce brand and sales content, direct external creative resources, and support PR and executive thought leadership. This hands-on individual-contributor role partners closely with the CMO and RevOps while building the marketing function for a high-growth enterprise AI startup.

Sell commercial insurance products through inbound and outbound calls, assess customer needs, recommend coverage, finalize sales, maintain regulatory and carrier compliance, and manage follow-ups. The role also resolves complex inquiries, develops referral-partner relationships, maintains Property and Casualty licensing, and mentors inside sales specialists. This is a remote position requiring reliable wired internet and a dedicated workspace.

Supports payroll and PEO-related functions for employers in HireWith’s network. Candidates may be matched with payroll service bureaus or PEO companies nationwide and receive personalized job-search, resume, and interview support. Ideal candidates have at least one year of payroll service bureau or PEO experience and familiarity with payroll systems such as UKG Ready, isolved, Asure Evolution, ExecuPay, MPAY, IRIS Payroll, or MasterTax. The position is remote and services are free to candidates.

Remote Human Resource Business Partner opportunities supporting clients of payroll, HR, and PEO companies. Candidates are considered for multiple nationwide roles and receive interview and resume support. Ideal qualifications include at least one year working for a payroll service bureau or PEO in HRIS, Benefits, or Time modules using platforms such as UKG Ready, isolved, Asure Evolution, ExecuPay, or similar systems.

The job involves connecting candidates with B2B sales positions in payroll services or PEOs, providing personalized support and interview preparation.