Top Tech Jobs & Startup Jobs in Chicago, IL

The Product Analyst connects product vision with software development by translating customer needs into user stories, acceptance criteria, and prioritized backlogs. They support Agile sprint planning, product roadmap development, stakeholder communication, release planning, and customer workflow research. The role gathers feedback, evaluates competitors, identifies risks and opportunities, and ensures development teams understand business goals and expected outcomes.

Support participants in personal development programs, facilitate goal-focused conversations, engage prospective clients using provided tools, and attract leads through social media and digital platforms. The role is remote, independent, flexible, performance-based, and includes structured training, leadership development, and ongoing professional learning. Compensation is based on profits from sales.

Lead and scale company-wide people operations for a fast-growing digital consultancy. Oversee talent acquisition, HR compliance, HRIS management, compensation benchmarking, performance management, engagement, learning, succession planning, DEI initiatives, and partnership with business leaders. Manage recruiting leadership, onboarding/offboarding, and data-driven people programs while supporting government contracting requirements and occasional travel.

Build backend architecture and infrastructure for LLM-driven agent systems, including orchestration, tool integration, context management, evaluation, observability, and production deployment. Develop services connecting AI models with insurance data and platform APIs, define reliable AI-native architectural patterns, and collaborate with product, design, and engineering teams to deliver underwriting workflows.

Support Total Rewards operations across benefits, compensation, and recognition. Tasks include processing benefits invoices and claims, administering recognition and compensation platforms, assisting with audits and open enrollment, supporting merit/promotions, maintaining SOPs and reports, and responding to employee inquiries.

Manages customer accounts receivable by posting payments, monitoring aging balances, following up on overdue invoices, resolving billing discrepancies, reconciling accounts and unapplied cash, preparing reports, supporting month-end close and audits, and documenting collection activities. The coordinator collaborates with Sales, Customer Service, Accounting, customers, and management to maintain accurate records and improve collection effectiveness.

Owns enterprise sales across Northeast State, Local, and Education accounts, including state agencies, municipalities, and universities. Responsibilities include full-cycle selling, executive engagement, pipeline development, public-sector procurement navigation, pilot conversion, multi-year contract growth, and contributing to SLED-specific pricing and go-to-market strategy. The role requires cybersecurity fluency, strong public-sector relationships, complex deal-closing expertise, and comfort building a territory in an early-stage company.

Owns the reliability, security, performance, and availability of AWS-hosted healthcare infrastructure. Builds infrastructure as code, CI/CD automation, monitoring, observability, backup and disaster recovery capabilities. Leads incident response, optimizes cloud resources, implements security controls, supports customer onboarding and migrations, and ensures compliance with healthcare privacy and software lifecycle requirements. Participates in on-call rotations and provides technical guidance to engineering and support teams.

Senior Product Designer responsible for designing complex clinical and operational workflows across a digital health platform. The role includes user research, prototyping, design-system management in Figma, accessibility and safety compliance, AI-enhanced design workflows, competitive analysis, and close collaboration with Product, Engineering, Data, and clinical teams. This temporary, fully remote position also involves mentoring designers, documenting decisions, and delivering validated designs for implementation.

Performs advanced accounting and reporting across labels and affiliates, including monthly close, complex journal entries, reconciliations, variance analysis, intercompany accounting, and financial reporting under U.S. GAAP. Reviews staff and offshore team deliverables, supports audits and tax reporting, ensures SOX and internal-control compliance, and identifies BlackLine automation opportunities.