Top Tech Jobs & Startup Jobs in Chicago, IL

Annotate tax forms by researching layouts, drawing precise bounding boxes, defining field schemas and relationships in Label Studio, exporting JSON/YAML, validating overlays, and documenting metadata and formulas for downstream model training.

Lead product strategy and execution for a new PC gaming product, build and manage cross-disciplinary teams, define metrics and roadmap, find product-market fit, and represent the product externally while aligning stakeholders and driving growth.

The Senior Software Engineer will enhance development workflows, mentor team members, collaborate on code reviews, and analyze data trends in Firefox development.

Evaluate and annotate AI-generated responses, write prompts and expected outputs, provide structured feedback, maintain high-quality training datasets, and collaborate with engineers to improve LLM performance and evaluation workflows.

Design intuitive web and mobile experiences through user research, wireframes, prototypes, and high-fidelity mockups. Maintain and contribute to design systems, ensure accessibility (WCAG), collaborate with product managers and developers, validate designs via testing, and present concepts to clients while balancing user needs and business goals.

Own the full enterprise sales cycle for large, strategic accounts: run multi-stakeholder deals, build consultative value-based business cases, demonstrate Dovetail's AI-native platform, develop account plans, maintain executive relationships, and help mature enterprise go-to-market.

Outbound-focused SDR responsible for researching target accounts, running personalized, segment-specific multi-touch cadences, qualifying prospects, booking SQLs for AEs, maintaining HubSpot CRM, and iterating on playbooks with the sales team.

Acquire and edit primarily romance titles, manage 5–8 titles yearly, develop manuscripts, negotiate terms, prepare marketing and jacket copy, coordinate with production/design/marketing/publicity, maintain agent and author relationships, and shepherd books through acquisition to publication.

Support two nonfiction editors with manuscript management, production tracking, stakeholder communication, submissions review, research for comparative titles and P&Ls, draft title and jacket copy, and general administrative tasks across editorial and other departments.

Serve as strategic HR partner to Rx Operations leadership: design talent strategy, organizational design, performance and talent management, manager coaching, employee relations, and data-driven people insights to drive culture and workforce scaling in a fast-growing healthcare operations environment.

Design, develop, and support Dynamics 365 and Power Platform solutions (Model-Driven Apps, Dataverse). Build server-side plugins and integrations with C#/.NET, implement client-side JS and PCF controls, create data integrations, manage Git-based CI/CD, troubleshoot production issues, and maintain technical documentation.

Lead data engineering and governance efforts for the SHARP system by analyzing business requirements, designing solutions, documenting user needs, implementing master/reference data and data quality rules using Informatica tools, and collaborating across organizational units to improve systems and reporting.

Lead FedRAMP program activities for a FedRAMP Moderate SaaS offering: manage continuous monitoring, POA&Ms, assessments, and FedRAMP 20x transitions; coordinate with engineering, 3PAO, agencies and infrastructure providers; develop policies, translate controls into implementable tasks, and support security-related RFP responses and customer briefings.

Serve as strategic HR partner to the COO for Rx Operations, designing talent strategies, organizational design, performance and talent management, manager coaching, employee relations, and data-driven people insights to support growth and ensure regulatory-compliant, high-performing teams.