Top Tech Jobs & Startup Jobs in Chicago, IL

Leads technical direction for GitLab’s Core DevOps services, covering CI, CD, planning, and source control. Defines architecture, quality metrics, migration strategies, and technical roadmaps; addresses systemic risk and complex design decisions; prototypes and writes code when needed; partners with Infrastructure, Security, SRE, and Product; adopts AI capabilities; mentors senior engineers; supports incident response and senior technical hiring.

Lead hands-on product security architecture across GitLab, including design reviews, threat modeling, systemic risk remediation, security standards, prototypes, and reusable developer guardrails. Partner with engineering and product leaders, secure distributed systems and software supply chains, guide AI coding tool security, mentor security engineers, and influence technical direction through proactive architecture and clear communication.

Create technical content, videos, demos, presentations, and product walkthroughs showcasing GitLab’s DevSecOps and AI agent capabilities. Engage developers, customers, sales teams, and online communities through webinars, events, forums, Discord, and social platforms. Answer technical questions, deliver analyst briefings, research the developer tools landscape, test new features, and provide product feedback. The role is remote, supports U.S. and Canadian time zones, and requires up to 20% travel.

Build and manage strategic customer relationships, drive enterprise sales growth, and help organizations adopt GitLab’s AI-powered DevSecOps platform. This is a future pipeline opportunity with responsibilities and requirements to be finalized. The role is remote globally, subject to location-based eligibility requirements.

Leads Professional Services operations by building scalable planning, forecasting, capacity, resource management, delivery, financial, and reporting processes. Partners with Finance, Sales, Customer Success, Engineering, and Delivery to improve PSA, CRM, time-tracking, automation, service pricing, revenue recognition, and go-to-market alignment. Provides leadership visibility into pipeline, staffing, utilization, project economics, margins, and growth while driving operational maturity across distributed services organizations.

Generates qualified meetings and sales pipeline through inbound lead management, account research, discovery conversations, and multichannel outreach. Collaborates with marketing and sales teams to develop target lists, messaging, and call strategies. Tracks activities in Salesforce and Outreach.io, reports results, documents processes, and mentors new SDRs. The role is fully remote and includes onboarding and training in GitLab and DevOps.

Owns execution and outcomes for the Chief Customer Officer’s strategic portfolio, including go-to-market transformation, retention and renewal programs, product feedback loops, and executive account engagement. Converts executive direction into structured workstreams, coordinates senior cross-functional stakeholders, monitors program health and business metrics, escalates risks, drives accountability, and recommends scope or prioritization changes. The role also establishes operating standards for a growing programs function in a globally distributed environment.

Build reusable backend platforms and developer-facing tooling for performance testing, analysis, reporting, and AI-assisted engineering workflows. Enable service teams to independently incorporate performance testing into development and CI workflows through self-service capabilities, documentation, templates, diagnostics, and guidance. Partner with engineering teams, influence adoption, generalize solutions, and provide expertise on complex performance challenges.

Leads cross-team backend initiatives and technical architecture for GitLab’s Core DevOps platform. Responsibilities include modernizing a monolith, establishing service, API, data, security, testing, and observability standards, guiding Go and Kubernetes practices, supporting Rust adoption, participating in incident response, mentoring engineers, reducing technical debt, and advancing AI-assisted engineering workflows.

Lead sales enablement for GitLab’s Public Sector business across Federal, State, Local, and Education markets. Develop tailored training, content, job aids, assessments, onboarding, and compliance guidance; partner with sales leadership and cross-functional teams; support procurement and contracting processes; align enablement with product launches and industry events; train teams on Salesforce, Clari, Claude, and related tools; and measure program effectiveness against business outcomes.