Top Tech Jobs & Startup Jobs in Chicago, IL

Lead a team of 4–5 engineers building and operating a cloud-scale SaaS document management platform. Responsibilities include people development, architecture, technical decision-making, AI-native software development, partner collaboration, roadmap execution, and engineering best practices such as CI/CD, testing, code reviews, documentation, and observability.

Develop and maintain Python-based automated tests for Windows desktop applications. Build UI automation suites with WinAppDriver or Appium, manage Azure test environments, integrate testing into GitHub Actions, and write PowerShell setup scripts. Diagnose flaky tests and CI failures, document defects and test coverage, participate in code reviews, and collaborate with QA, development, and DevOps teams to support reliable releases.

Own product strategy and roadmap for information governance features (records management, matter mobility, threat analytics, compliance). Drive customer-informed requirements, prioritize backlog, run advisory panels, collaborate across engineering/design/GTm, monitor competition, and deliver governance capabilities that enable secure, compliant information lifecycle management.

Lead enterprise security strategy and architecture, create repeatable secure reference architectures and developer guardrails, perform threat modeling, embed Security by Design across product lifecycles, mentor senior security staff, evaluate third-party tech, and communicate technical risks to business leaders to enable secure, scalable SaaS growth.

Manage a portfolio of strategic enterprise law firm customers, driving adoption, retention, loyalty, expansion, and net revenue retention. Serve as the central customer contact, conduct executive business reviews, develop success plans, monitor customer health, resolve blockers, and coordinate with sales, product, support, engineering, training, cloud services, and partners. Provide strategic guidance based on account intelligence and legal industry trends while identifying renewal risks and growth opportunities.

Manages governance, security, compliance, and operational integrity for enterprise SaaS applications. Responsibilities include application audits, access reviews, identity governance, application evaluations, documentation, health monitoring, support ticket triage, compliance reporting, application rationalization, and change management. The role partners with IT and business stakeholders, supports provisioning and deprovisioning workflows, and provides occasional off-hours support during maintenance and deployments.

Leads vision, strategy, and roadmap for iManage’s next-generation AI-native document and email management platform. Validates customer needs, unifies adjacent products, prioritizes engineering delivery, and launches features across cross-functional teams. Presents product vision to customers, executives, partners, and market audiences while monitoring competitors and developing differentiation. Requires extensive SaaS product management experience, cloud and content security knowledge, strong customer engagement, analytical skills, and cross-functional leadership.

Lead incident response and reliability improvements for iManage Cloud. Triage large-scale production issues, build observability and automation, run postmortems, partner with product and engineering, and proactively detect and eliminate systemic problems to improve uptime and customer experience.

Lead multi-year product strategy and roadmaps for a major platform area, prioritize reusable platform services, partner with engineering and cloud teams for scalability and reliability, participate in API and architecture decisions, integrate AI/ML capabilities, drive go-to-market launches, track product success metrics, and align stakeholders across the organization.

Negotiate and close high-volume enterprise SaaS and cloud agreements across the Americas. Review and redline customer paper, apply playbooks, manage concurrent deals, support sales escalations, and collaborate with cross-functional teams to ensure consistent, commercially minded legal positions.