Top Tech Jobs & Startup Jobs in Chicago, IL

Lead US business development for insurance carriers, brokers, and InsurTechs. Build pipelines, manage complex sales cycles, tailor data/AI software solutions, create ROI case studies, and collaborate cross-functionally to close contracts and inform commercial strategy.

Serve as the founding engineering leader: design and build the 0-to-1 enterprise SaaS platform, own technical vision and architecture, work hands-on with customers, establish engineering standards and security posture, hire and grow a small senior engineering team, and evolve into Head of Engineering/CTO.

Provide advanced technical support for Aerospike customers: troubleshoot complex issues, collaborate with engineering, assist deployments and performance tuning, write KB documentation, and participate in on-call incident response.

Design and develop instructor-led, virtual, and digital learning using AI-enhanced tools; create storyboards, assessments, multimedia video and avatar assets; manage projects, stakeholders, and LMS publishing.

Design and build cloud-native, JVM-based systems powering an AI-driven retail data platform. Collaborate with product, data, and engineering teams to deliver scalable microservices, continuous deployment pipelines, and production-ready solutions while owning technical direction and operational reliability.

Process and review financial aid packaging, disbursements, verifications, R2T4s, credit balances, and adjustments while ensuring compliance with federal and state regulations and supporting departmental KPIs and projects.

Serve as primary customer contact to onboard, drive adoption, and ensure customer success for SaaS security products. Build executive relationships, maintain success plans and health scores, coordinate with Sales, Product, and Professional Services, and drive renewals, upsell and cross-sell opportunities while escalating risks and ensuring high customer satisfaction.

Build and maintain Salesforce reports/dashboards, analyze marketing and funnel performance, partner with Marketing/RevOps, experiment with AI-driven data/enrichment workflows, ensure data quality across systems, and present insights to leadership.

Serve as the strategic post-implementation advisor for enterprise accounts, driving adoption, retention, and expansion. Lead QBRs, monitor account health and usage, identify upsell opportunities, coordinate with Product/Engineering, maintain records in Planhat, and travel to customer sites (~25%).

Serve as a liaison between business stakeholders and development teams to elicit, translate, and document requirements into Gherkin-format user stories with testable acceptance criteria. Support agile ceremonies, assist with smoke testing, track requirements to completion, and ensure delivered digital assets meet business expectations. Collaborate with Product Owners, QA, and engineers throughout the SDLC.