Top Tech Jobs & Startup Jobs in Chicago, IL

Build and operate foundational developer infrastructure across CI, build systems, deployment orchestration, and test platforms. Improve build speed, deployment safety, test reliability, observability, and engineering productivity at scale. Own services from architecture through production, including SLOs and on-call operations. Lead cross-functional technical projects, partner with engineering teams, mentor engineers, and shape platform strategy.

Test mobile features across iOS and Android, perform regression testing, and build automated synthetic tests for voice calls and SMS. Develop test plans for new and cross-team initiatives, track bugs and quality trends, and provide data-driven recommendations. Collaborate closely with engineering, product, and design teams to maintain quality while increasing release velocity.

Lead product strategy and execution for Squarespace’s customer engagement platform, including CRM, email campaigns, automations, transactional communications, and SMS. Own the Email Campaigns business line, revenue performance, go-to-market strategy, and roadmap. Build and mentor a multi-product product management team, partner with engineering, design, commercial, and marketing leaders, and use data and AI to improve automation and personalized engagement.

Leads the company’s information security operations and reports to the CISO. Oversees SIEM, threat detection, vulnerability management, penetration testing, incident response, SOC 2 Type II compliance, third-party risk, security awareness, cloud and endpoint security, and regulatory cybersecurity coordination. Manages security policies, breach readiness, tabletop exercises, KPIs, audits, and emerging technology evaluations while partnering with IT, infrastructure, compliance, regulators, and executive leadership.

Support the legal team by managing the contract lifecycle: draft, review, revise, and track agreements; assist negotiations; maintain contract database and key dates; perform legal research; prepare reports; coordinate stakeholders to ensure compliance and timely execution.

Build and maintain cross-platform Flutter applications for iOS and Android. Responsibilities include implementing state management, integrating RESTful APIs and external services, troubleshooting bugs, optimizing performance, reliability, security, and user experience, and managing app store deployments. The role involves collaborating in an agile team, contributing proactively to product decisions, and continuously improving mobile applications.

Own end-to-end network reliability across data centers, AWS, and GCP, including routing, switching, DNS, load balancing, service mesh, VPNs, circuits, and cross-connects. Automate network configuration with Ansible, Terraform, GitOps, CI validation, and IPAM. Engineer failover, observability, security hardening, client connectivity, and Kubernetes ingress while participating in an interrupt-contained on-call rotation.

Administer and enhance Edmunds’ Databricks data platform and AWS infrastructure. Build and maintain ETL pipelines, infrastructure-as-code tooling using Terraform or CDK, and operational dashboards, alerts, and reports. Collaborate with business, engineering, analytics, security, and infrastructure teams to support data platform users and AI solutions. Evaluate new technologies, troubleshoot platform issues, and improve operational, cost, and security visibility.

Leads the payments and banking product roadmap for a regulated cannabis fintech platform. Owns product vision, KPIs, market research, compliance requirements, partner integrations, prioritization, and customer adoption. Collaborates with executives, financial institutions, fintech providers, designers, engineers, marketing, and account teams to launch embedded payment, banking, liquidity, and credit capabilities.

Leads enterprise sales and strategic customer relationships for RigUp’s downstream energy solutions. Responsibilities include prospecting, pipeline management, proposals, negotiations, onboarding, account growth, market development, and cross-functional coordination with Operations, Product, Marketing, and Leadership. The role requires deep downstream oil and gas expertise, C-suite relationship development, complex RFP ownership, frequent client travel, AI-enabled sales workflows, and mentorship of account team members.