Top Tech Jobs & Startup Jobs in Chicago, IL

Lead global accounting operations and financial reporting across 14 international entities. Manage a 15-person finance team, oversee US GAAP and statutory compliance, direct consolidations and close processes, improve accounting workflows using modern technology, and provide accurate reporting to executives, the board, banks, and investors. Establish scalable policies, automate processes, manage accounting functions, and support the company’s rapid growth.

Source, engage, assess, and manage executive-level candidates for clients. Coordinate interviews, manage candidate expectations, maintain pipelines and networks, collaborate with sourcing, and deliver high-quality placements in a remote environment.

Develop and maintain complex GIS maps, applications, geodatabases, web services, spatial data models, ETL workflows, and custom geoprocessing tools. Translate client processes into GIS requirements and solutions, manage data quality and enterprise geodatabases, support SQL Server, conduct geospatial analyses and modeling, document systems, coordinate data exchanges and training, and provide remote or on-site client support.

Own long-term relationships with enterprise legal and marketing teams from go-live through renewal. Drive product adoption, expansion, account health, executive business reviews, measurable customer value, and renewal support. Configure the platform, analyze usage, manage customer cadence, translate feedback into product input, and build Blee’s customer success playbook. The role requires enterprise SaaS experience, technical fluency, executive communication, and 10–20% customer travel.

Leads two vertical software businesses with full ownership of revenue, retention, profitability, cash management, product direction, organizational structure, and customer relationships. Builds repeatable sales and renewal motions, manages public-sector procurement, allocates capital across functions, evaluates teams, and sets coordinated product strategies while preserving each business’s identity. The role requires hands-on selling, P&L leadership, founder-transition experience, and approximately one week of travel per month.

Own enterprise sales in Ohio and Michigan selling Axonius cybersecurity solutions to organizations >2,000 employees. Build a 4x pipeline, execute value-based selling (MEDDPIC), manage complex multi-stakeholder deals, partner with channels and internal teams, maintain Salesforce/Clari hygiene, and deliver accurate forecasts to exceed revenue targets.

The People Analytics and HRIS Analyst develops workforce dashboards, reports, visualizations, and trend analyses using HR data. The role supports Workday reporting, configuration, data quality, governance, testing, and HRIS changes. It partners with HR leaders and business stakeholders to translate workforce questions into actionable insights related to retention, hiring, compensation, talent, engagement, and organizational effectiveness. The analyst also establishes reporting standards, ensures data security, and educates stakeholders on interpreting people analytics.

Coordinate inland shipments by rail, truck, barge, and feeder vessel; handle customer inquiries; arrange transport bookings; manage cargo release, customs, and dwell-time issues; liaise with vendors, terminals, legal/insurance, and internal teams to ensure timely, cost-effective intermodal operations and claims documentation.

Own commercial legal work, including drafting and negotiating enterprise technology agreements, SaaS licenses, partnerships, reseller arrangements, procurement contracts, and data processing agreements. Advise on AI product terms, data rights, intellectual property, cybersecurity testing permissions, liability, and risk allocation. Partner with Sales, Finance, Product, Engineering, and Security, while building scalable legal processes, templates, playbooks, and training. The role requires independently leading complex negotiations and supporting a growing technology startup.

Performs actuarial calculations and analyses across product development, financial management, reserving, experience studies, risk management, reporting, and regulatory requests. Investigates data and assumption issues, prepares reports and presentations, supports audits and research, and improves actuarial processes using emerging technologies and AI-enabled tools. Collaborates with Accounting and Operations while progressing toward ASA and FSA designations.