Top Tech Jobs & Startup Jobs in Chicago, IL

Own and evolve Tenna's production platform: operate and improve AWS-based infrastructure (EKS, RDS/Aurora), lead incident response and RCA, implement IaC (AWS CDK), manage CI/CD (GitHub Actions), monitoring, cost optimization, and documentation to build a platform/developer-experience function.

The Principal Data Engineer will lead data architecture initiatives, design scalable data systems, and oversee data standards across teams while ensuring high-quality data infrastructure and guiding engineering teams.

Designs and delivers sales onboarding and ongoing training for Tenna's sales team, creates multimedia course content, coaches reps through shadowing and feedback, measures training effectiveness with ramp and performance metrics, and continuously updates curriculum in partnership with sales, product, and leadership.

The Principal Architect will lead the technical direction of Tenna's platform by designing scalable systems, establishing standards, and guiding teams in implementing the technical strategy while ensuring system reliability and performance.

Support end-to-end contract lifecycle administration: execute contracts, renewals, and addendums; review and validate contract data, pricing, and terms; coordinate with Sales, Customer Success, and Finance; maintain accurate records, perform audits, and drive process improvements to ensure revenue and data integrity.

Lead full-cycle recruiting strategy and execution for Sales, Customer Success, and support teams. Build proactive sourcing pipelines, optimize candidate experience and ATS data hygiene, develop structured interviews and scorecards, manage employer branding and recruiting events, monitor diversity metrics, and partner with leadership on workforce planning, internal mobility, and hiring SLAs.

Designs and builds responsive, accessible WordPress/Elementor pages and marketing assets; writes HTML/CSS/JS; maintains design system and brand standards; creates digital and print creative in Adobe CC and Figma; runs A/B tests and reports performance; partners with engineering and marketing teams.

Own and maintain the WordPress platform end-to-end: hosting, security, performance, technical SEO, tracking (GA4/GTM), integrations (HubSpot/APIs), backups, and documentation. Establish environments, deployment workflows, monitoring, and runbooks while partnering with front-end and marketing teams to ensure reliable, high-performing, and compliant site operations.

Lead full-cycle recruiting for a portfolio of roles: source, screen, manage candidates, and partner with hiring managers. Build sourcing strategies, maintain ATS hygiene and recruiting data, run events and partnerships, ensure compliance, and optimize candidate journey to support scaling hiring needs.

The Insurance Partnerships Manager leads relationship development across the insurance ecosystem, fostering partnerships, managing contracts, and driving revenue growth while collaborating across teams to deliver joint programs and client value.