Top Tech Jobs & Startup Jobs in Chicago, IL

Owns audit evidence collection, technical control validation, continuous monitoring, and compliance documentation across FedRAMP, ISO 27001, ISO 42001, SOC 2, and NIST frameworks. Partners with IT, Engineering, and DevOps teams, supports external assessors, automates evidence collection, tracks remediation, and contributes to risk assessments, threat modeling, vendor reviews, and AI security safeguards.

The role involves delivering client financial projects, leading workstreams, mentoring consultants, and contributing to internal business development.

Own and evolve Looker as the company-wide business intelligence platform. Build dashboards, data models, pipelines, and integrations connecting Snowflake and other sources. Ensure data quality and provenance, support operational reporting, and partner with Finance, Data Science, and business teams. Help develop AI- and LLM-based agentic reporting tools that enable self-service analytics. Communicate technical concepts across the organization and provide insights for operational decision-making.

Leads Parisleaf’s Strategy discipline, overseeing strategic methodologies, quality standards, team development, and complex partner engagements. Provides senior counsel, facilitates executive workshops, guides research and insight development, and ensures strategy translates into creative and fundraising outcomes. Collaborates across Creative, Operations, Business Development, and Leadership while supporting business growth, partner relationships, agency planning, and thought leadership. The role is fully remote within the continental United States, with required travel.

Hands-on Site Reliability Engineer responsible for production support, incident response, root cause analysis, observability, SLI/SLO development, synthetic monitoring, automation, and toil reduction. The role partners with software engineering to resolve application, database, API, and infrastructure issues, implement permanent fixes, improve reliability practices, and support a rotating on-call schedule.

The Payroll Customer Success Manager serves as the main contact for customers, supporting onboarding, ensuring payroll accuracy, resolving issues, and building trust through proactive communication.

Improve AWS production infrastructure reliability, observability, performance, and operational maturity. Build Terraform infrastructure, enhance CI/CD, automate operational work, manage incident response and on-call operations, lead postmortems, improve application resilience, support capacity planning and database reliability, and collaborate on security hardening and compliance. Mentor engineers and promote reliability practices across the organization.

Provides strategic in-house legal support focused on vendor, technology, professional services, and healthcare agreements. Drafts and negotiates contracts, manages the contract lifecycle, advises on healthcare regulatory and compliance matters, partners with executives on business risks, develops legal training, promotes CLM tools, and manages outside counsel. Requires a law degree, active state bar membership, and at least four years of legal experience.

Lead and grow Proof’s IT Engineering team while transforming corporate IT from reactive help desk support into an engineering-first function. Own the strategy and roadmap for identity, access, endpoints, SaaS, vendors, procurement, and budgeting. Mentor engineers, implement infrastructure-as-code, CI/CD, GitOps, automation, and AI-driven operations, reduce ticket volume through root-cause fixes, and partner with InfoSec on security and compliance.

Leads complex telecommunications and network modernization programs involving multiple projects. Coordinates project managers, technical teams, vendors, and business stakeholders; manages integrated plans, governance, risks, dependencies, resources, budgets, and forecasts. Ensures operational readiness, production transitions, stakeholder communication, strategic alignment, and benefits realization. Supports continuous improvement and maintains delivery discipline across technology initiatives.