Top Tech Jobs & Startup Jobs in Chicago, IL

Develop user interface and user experience designs using Figma, requiring at least six years of experience. Candidates must be eligible to work in the United States.

Set the technical direction for machine learning at Payabli by maturing production risk models and launching new models across the payments lifecycle. Establish experimentation, monitoring, drift detection, benchmarking, retraining, and incident-response foundations. Translate payments challenges into modeling opportunities, connect model performance to business outcomes, influence the ML roadmap, and mentor engineers while partnering with product, engineering, and risk operations.

Build agentic LLM systems that acquire, clean, validate, curate, and document large-scale biomedical datasets for multimodal model training. Develop reliable agent architectures, tooling, evaluation harnesses, quality-control workflows, and reproducible data pipelines. Collaborate with ML scientists, monitor distributed production pipelines, diagnose failures, and implement secure sandboxed execution with restricted access and audit logging.

Owns the product backlog and translates user needs into JIRA tickets, user stories, and acceptance criteria. Partners with Product Management, Engineering, QA, and cross-functional stakeholders on prioritization, release planning, testing, and delivery. Monitors feature adoption, gathers feedback, advocates for end users, and supports business cases and ROI analysis. The role requires understanding healthcare workflows and facilitating communication among technical and business teams.

Own quality engineering for high-throughput payment systems by architecting automated regression, performance, stress, and load testing. Build emulators for external payment systems, integrate quality gates into CI/CD pipelines, validate microservices, event-driven architectures, and databases, and use Prometheus and Grafana for observability. Apply AI-assisted testing, synthetic data generation, and edge-case analysis while mentoring engineers and preventing incidents through telemetry-driven testing and post-mortems.

Provides high-level executive support to the CEO and leadership team, managing complex calendars, travel, meetings, confidential matters, and follow-through. Writes and edits executive and company-wide communications, coordinates all-hands and leadership events, prepares Board materials, and supports change communications. Improves executive-office workflows using Microsoft 365, AI tools, templates, trackers, and repeatable processes.

Lead and oversee volunteer HR operations: supervise/train HROs, manage recruiting and onboarding via Dover ATS, maintain HR documentation and systems, run meetings and strategic HR initiatives, support Executive Director on DEI and people strategy, and cover day-to-day volunteer HR duties.

Lead Roo’s sales organization and integrated revenue strategy across its veterinary staffing marketplace. Responsibilities include designing territory and coverage models, allocating headcount and budget, improving forecasting and quota attainment, scaling go-to-market playbooks, building enablement and coaching programs, managing CRM and sales tooling, planning organizational capacity, and aligning Product, Marketing, Finance, and Data around revenue priorities. The VP will also lead hiring, performance management, and major sales process and compensation transformations.

Serve as a Workday Financials subject matter expert supporting production issues, implementations, module rollouts, upgrades, reporting, dashboards, integrations, security roles, and finance processes. Partner with Finance and Accounting teams to gather requirements and deliver Workday solutions. Maintain Prism datasets and analytics, support close activities, troubleshoot integrations, test releases, and provide documentation, training, and end-user support.

Own relationships and net revenue retention across 40–60 enterprise healthcare customers. Drive adoption, renewals, upsells, and cross-sells through account planning, executive check-ins, QBRs, forecasting, and consultative partnership. Monitor account health using Freshpaint, Looker, and HubSpot; coordinate cross-functionally to remove blockers and improve customer outcomes. Travel up to 30% for onsite visits, conferences, and company events.