Top Tech Jobs & Startup Jobs in Chicago, IL

Leads and develops a DevOps platform team responsible for AWS-based developer platforms, CI/CD pipelines, Terraform, EKS, service onboarding, connectivity, secrets, observability integration, and environment promotion. Drives automation, AI-assisted DevOps workflows, platform reliability, security controls, incident response, compliance readiness, and cross-functional delivery. The role combines direct people leadership with hands-on technical oversight of scalable, self-service engineering infrastructure.

Owns Azure DevOps administration, governance, configuration, access controls, boards, organizational structures, and GitHub integrations for Engineering. Diagnoses platform issues, automates administrative tasks, maintains standards and documentation, supports onboarding, tracks platform health and compliance, and contributes to adjacent tools such as LaunchDarkly, Flyway, Cursor, and Claude Code.

Administers and governs engineering platforms including Azure DevOps, LaunchDarkly, Flyway, Cursor, and Claude Code. Manages access controls, feature flags, database migrations, standards documentation, platform health, compliance evidence, and automation. Builds monitoring, enablement resources, and workflow improvements while supporting secure, reliable engineering operations. Senior-level responsibilities also include leading complex integrations, automation strategy, technical mentoring, and AI tooling evaluation.

Develops and maintains AI governance policies, frameworks, and controls aligned with regulatory and industry standards. Conducts AI model risk assessments covering bias, explainability, data quality, and security; evaluates organizational and vendor risks; supports audits; designs controls; and partners with Legal, Privacy, Security, and Technology teams. The role also promotes compliant AI practices and organizational awareness while applying advanced AI/ML knowledge.

The Sales Executive develops and manages a territory pipeline, identifies prospective clients, and sells Origami Risk’s integrated risk management SaaS solutions. Responsibilities include consultative discovery, product presentations, pricing and statement-of-work preparation, competitive positioning, networking with risk and insurance professionals, and achieving annual sales quotas. The role requires strong direct SaaS sales experience, CRM proficiency, and the ability to sell to organizations across multiple industries.

Leads cloud infrastructure, platform operations, and security operations for a SaaS environment. Oversees reliability, scalability, incident response, compliance, disaster recovery, IAM, observability, automation, and secure cloud architecture. Drives AI-powered monitoring, anomaly detection, remediation, security analytics, and operational efficiency. Manages Cloud Architecture, Infrastructure, and Security Engineering teams, including hiring, mentoring, performance management, and strategic planning.

Manages a portfolio of SMB and mid-market clients throughout onboarding, adoption, value realization, renewal readiness, and expansion. Builds stakeholder relationships, develops success plans, monitors client health and usage metrics, leads business reviews, identifies risks, manages escalations, and coordinates Support, Product, Professional Services, Training, Technical Account Management, and Account Management teams. Documents client goals and feedback while applying risk management, insurance, and industry expertise to deliver measurable outcomes.

Owns the RMIS product roadmap, strategy, backlog, and Agile delivery. Partners with Engineering, stakeholders, marketing, and operations to define requirements, prioritize features, support Scrum execution, and ensure quality delivery. Uses data, analytics, experimentation, and AI-assisted techniques to identify opportunities, prototype solutions, guide decisions, and develop responsible AI-enabled features. Acts as the product subject matter expert and supports strategic planning, client responses, and product lifecycle activities.