Top Tech Jobs & Startup Jobs in Chicago, IL

Lead RMF execution and authorization efforts for classified cloud and AI-integrated systems. Develop and maintain SSPs, SARs, POA&Ms, and continuous monitoring documentation; assess NIST, DoD, CNSS, FedRAMP, cloud, container, and AI security controls. Conduct architecture reviews, threat modeling, vulnerability assessments, risk analysis, and security control assessments while coordinating with architects, developers, DevSecOps teams, customers, and third-party assessors.

Own general ledger accounting, monthly close, and balance sheet reconciliations; prepare journal entries and variance analysis; improve processes using AI/automation; lead year-end audit coordination; ensure GAAP compliance and support tax activities.

Staff Software Engineer responsible for technical strategy, architecture, complex feature design, implementation, scalability, and greenfield development. The role mentors engineers, leads design and code reviews, drives technical alignment, addresses technical debt, participates in hiring, and remains a hands-on contributor to full-stack enterprise software development using technologies such as PHP, Laravel, Vue.js, and MySQL.

Supports the design and progressive ownership of Azure-based SaaS integrations, centralized data repositories, automated ETL/ELT pipelines, Power BI data models, and secure cloud workflows. Develops automation using Python, JavaScript, and JSON; troubleshoots APIs and authentication issues; documents integration processes; and collaborates with stakeholders. The role is intended for an early-career cloud engineer who will grow toward independently managing cloud data architecture and integration solutions.

Own the full enterprise sales cycle for cloud-based fire and EMS operations software, from prospecting and discovery through solution design, proposal, negotiation, and closing. Build strategic pipelines, manage complex government buying groups, align solutions to public safety needs, maintain CRM and forecast accuracy, and collaborate with Sales Engineering, Marketing, Implementation, and Customer Success. Guide agencies through GovTech procurement while driving new ARR growth and expansion.

Lead engineering strategy, architecture, AI-native product development, execution, hiring, and organizational growth. Partner with the CEO, leadership, and Product to build technical roadmaps, establish AI-assisted development and evaluation practices, improve infrastructure and engineering quality, and maintain delivery accountability. This hands-on leadership role requires coding credibility, product collaboration, talent development, cross-functional communication, and ownership of engineering metrics, culture, and technical direction.

Conduct high-volume outbound outreach through email, LinkedIn, and phone to engage business development prospects, schedule discovery calls, and support lead qualification. Maintain accurate lead and activity records in Zoho CRM, coordinate pre-sales activities, prepare client briefing documents, and ensure qualified opportunities are handed off to business development managers. The role also supports talent pipelines and requires strong communication, organization, follow-up, and multitasking skills.

Build and operate a GitOps-based DevSecOps software factory for federal customers. Develop infrastructure and configuration as code, AWS/EKS deployments, Helm charts, Kubernetes integrations, CI/CD pipelines, and automation scripts. Troubleshoot cluster environments, improve security hardening and compliance, contribute to open source, and collaborate through Agile ceremonies. The role requires active Secret clearance, U.S. citizenship, substantial Kubernetes and cloud experience, and specific security and Kubernetes certifications.

Lead enterprise automation architecture and delivery across RPA, workflow automation, process mining, intelligent automation, testing, bots, citizen development, and AI orchestration. Establish and operate an Automation Center of Excellence, identify high-value use cases, guide implementation, manage governance and regulatory alignment, support training and adoption, and track financial value. Work hands-on with business stakeholders, technology teams, vendors, and external consultants in a regulated life sciences environment.

Own the full sales cycle for an early-stage AI recruiting platform: prospect, demo, negotiate, close deals, build pipeline, refine outbound strategy with the CEO, represent the company at events, and coordinate handoffs with Customer Success to ensure long-term account health.