Top Tech Jobs & Startup Jobs in Chicago, IL

Owns executive reporting for autonomous vehicle system performance, including the weekly Software Performance Review and broader commercial readiness analyses. Synthesizes robotics data, diagnostic evaluations, and performance metrics into strategic narratives for senior leadership. The role aligns cross-functional engineering data, automates reporting pipelines and presentation generation, establishes visualization standards, and mentors junior engineers. It requires deep knowledge of robotics, autonomous vehicle performance, data architectures, executive communication, and AI-assisted development workflows.

Own the Dynamics 365 CRM and Dataverse platform, including architecture, configuration, security, customization, deployments, integrations, data quality, and support. Design Power Apps, Power Automate flows, and Power BI reports; lead upgrades, migrations, UAT, and releases; evaluate Microsoft capabilities; translate business needs into solutions; and mentor analysts and project team members.

Own Linkup’s Canadian market end to end, including strategy, pipeline, revenue, expansion, and full-cycle B2B sales. Build relationships across Canada’s AI ecosystem, represent the company at local events, and connect Canadian opportunities with US momentum. Partner with Product and Engineering on customer solutions and roadmap feedback, while creating repeatable sales playbooks for AI-native teams and enterprise innovation groups. The role requires prior technical or SaaS sales experience, market-building capability, strong Canadian AI connections, and regular travel between Canada, New York, and San Francisco.

Own the full sales cycle for Audit Manager, including prospecting, discovery, demonstrations, negotiation, and closing. Build pipeline through outbound efforts, engage healthcare revenue cycle stakeholders, identify billing and coding risks, maintain accurate HubSpot records, and partner with BDR, sales engineering, and Customer Success teams. Requires healthcare or revenue cycle sales experience, medical billing and coding knowledge, strong consultative selling skills, and experience managing $5K–$75K deals.

Design and maintain scalable full-stack software solutions using Python and Pandas. Develop data infrastructure, integrate technologies, optimize application performance, and collaborate cross-functionally to deliver reliable products. The role requires strong AWS and scalable architecture expertise, with a focus on continuous improvement and customer impact.

Design and build approximately three email campaigns daily using master templates and ESP platforms. Create email and popup graphics from client briefs, implement templates in Stripo, incorporate feedback accurately, and deliver designs within one to five days. The role requires strong graphic design skills, proficiency with Klaviyo, Mailchimp, Figma, Photoshop, Adobe Illustrator, and excellent written and spoken English.

Manage a portfolio of K-12 district customers as a strategic advisor to drive adoption, retention, and expansion. Deliver renewals and revenue targets, lead executive business reviews, surface customer feedback to product teams, and cultivate customer advocates. Collaborate cross-functionally to solve problems and maximize customer ROI.

Build and ship end-to-end features for a restaurant operating system, lead architecture and technical execution, define product roadmap with cross-functional teams, and maintain high-quality CI/CD and productionized systems.

Design, implement, test, release, and maintain scalable iOS application features. Collaborate with engineering and product teams, optimize application performance, produce documented code, estimate work, and maintain CI/CD pipelines. Requires strong Swift, SwiftUI, UIKit, concurrency, REST API, testing, Git, App Store submission, and continuous delivery experience.

Own the agent orchestration platform and co-lead AI agent solutions across the insurance lifecycle. Define agent roadmaps, prompts, tools, autonomy tiers, evaluation datasets, governance, rollout gates, observability, and cost controls. Partner with product, engineering, data, and experience teams to translate business needs into agent specifications and measurable outcomes. Establish regression testing, human escalation policies, audit trails, and production quality standards for LLM-powered products.