Top Tech Jobs & Startup Jobs in Chicago, IL

Serve as the right hand to the Head of Sales, running sales cadence, driving pipeline visibility and forecasting, enabling reps with materials, coordinating cross-functional GTM work, structuring strategic problems, supporting hiring/onboarding, and preparing executive-level communications to improve sales execution and accountability.

The Staff SDET will design and implement automated test frameworks using TypeScript, collaborate with developers, and enhance testing processes within CI/CD pipelines.

Leads and develops software engineers through mentorship, feedback, hiring, and career growth. Partners with product and design to deliver secure, scalable, reliable features; guides architecture and engineering best practices; improves processes, velocity, and execution; and translates customer and business needs into technical roadmaps. The role requires hands-on leadership in a high-growth startup environment and ownership of engineering culture, performance, reliability, and talent development.

Analyze product data to guide roadmap decisions, evaluate AI-powered capabilities, design experiments, build dashboards, and identify customer behavior patterns. Partner with Product, Engineering, and Design to define metrics, improve instrumentation, uncover friction points, and communicate insights that improve product outcomes and customer success.

Lead design, automation, and optimization of database infrastructure (PostgreSQL/Aurora). Build monitoring, tuning, and scaling strategies, create automation tooling, drive performance and reliability initiatives, and expand into broader SRE responsibilities to improve availability and system health for a growing SaaS platform.

Design and scale secure AWS environments, build and maintain Terraform IaC and pipelines, lead security assessments and incident response, integrate security into CI/CD, define IAM/encryption/network controls, monitor and investigate cloud threats, and coach teams on cloud security best practices.

Lead security architecture and design reviews, run penetration tests and threat modeling, build CI/CD security automation, secure AWS cloud and containerized workloads, develop security observability and incident response, manage bug bounty and vulnerability workflows, and create security standards, training, and roadmap.

Owner of the marketing intelligence stack: build warehouse-backed data models, integrate intelligence and CRM tooling, ship CEO-facing GTM dashboards, and design agentic LLM workflows (on Claude) for briefs, content, and account monitoring while ensuring compliance and observability.

Lead the strategy and execution of data and integrations for a software platform, ensuring alignment with customer needs, performance measurement, and compliance with industry standards.

The Staff Site Reliability Engineer will build and scale infrastructure for Assured's platform, automate delivery, enhance observability, and lead mentoring initiatives.