Top Tech Jobs & Startup Jobs in Chicago, IL

Lead customer migrations from self-managed GitLab to GitLab Dedicated using GitLab Geo. Plan replication, cutovers, network connectivity, and post-migration validation while debugging synchronization issues. Build repeatable automation, runbooks, and infrastructure validation using Terraform, Ansible, Kubernetes, and cloud platforms. Manage multiple customer engagements, advise stakeholders, communicate technical plans, and collaborate with Professional Services, Product, and Engineering teams.

Drive enterprise growth in the Seattle territory by leading complex B2B SaaS sales cycles for GitLab's AI-powered DevSecOps platform. Build C-level relationships, develop strategic account plans, coordinate cross-functional teams, manage full sales lifecycle from discovery to implementation, and drive net ARR and account expansion while contributing to forecasting and go-to-market improvements.

Lead the field organizations AI adoption by defining enablement roadmaps, identifying and piloting high-impact field use cases, driving operational scale, building field champions, and owning governance for safe, compliant AI tool adoption. Partner with product, engineering, ops, and analytics to measure impact and embed AI into day-to-day sales workflows.

Provide post-sales technical expertise to help customers adopt GitLab via webinars, labs, workshops, and consultative engagements. Collaborate with CSMs, AEs, and renewals to support implementations, architecture, CI/CD, SCM, DevSecOps, and Agile Planning. Create reusable enablement content and maintain specialty competency.

Maintain an inventory of AI tools, index field use cases, track adoption and utilization, manage access requests and provisioning, ensure AI data hygiene, produce simple reporting, and create communications and micro-enablement to drive field AI adoption.

Lead a team of Solutions Architects to support enterprise customers, drive technical evaluations, and promote successful adoption of the GitLab platform. Coach and mentor team members while ensuring alignment with sales and product management.

As a Business Development Representative at GitLab, you'll prospect targeted accounts, generate meetings, collaborate with teams, and engage buyers for the AI-powered DevSecOps platform.

Own and grow a portfolio of strategic and enterprise accounts in Poland. Lead full sales cycles, develop account plans, collaborate with pre/post-sales and channel partners, drive adoption and expansion of GitLab's DevSecOps platform, generate pipeline, and convey customer feedback to product teams.

Lead technical direction for a greenfield team building agentic/LLM-backed systems to reduce SDLC friction. Drive discovery through shipping, apply distributed-systems judgment at scale, mentor engineers, own technical hiring and cross-team alignment, and evaluate correctness and safety of agentic workflows.

Manage a named mid-market book of business, prospect and close SaaS deals, drive adoption and retention, forecast quarterly results, collaborate cross-functionally, and represent GitLab at events. Own account strategy, pipeline, and customer relationships while using sales frameworks (MEDPICC, Command of the Message) to meet quota and reduce churn.