Strategic Account Executive - Chicago

Title: Strategic Account Executive - Chicago Location: Remote, United States

Location- Chicago, Illinois 

An overview of this role

As a Strategic Account Executive for the Chicago area, you'll drive GitLab's enterprise growth by helping some of the area's most influential organizations adopt, implement, and expand their use of our AI-powered DevSecOps platform. You'll focus on enterprise accounts, guiding customers through complex digital and DevSecOps transformations and driving pipeline generation that translates into measurable Net ARR and long-term expansion. In this role, you'll act as a key connector between customer stakeholders and GitLab's field organization so GitLab is seen as a trusted, long-term partner across the full sales cycle. In your first year, you'll be expected to build a strong enterprise portfolio across your territory, create repeatable sales motions, and consistently forecast and report on deal progress and account health.

What you'll do

• Drive strategic growth by leading GitLab's enterprise accounts across Chicago, serving as a trusted technology advisor to industry leaders in your territory.
• Orchestrate winning sales strategies by bringing together Solutions Architects, Customer Success experts, Sales Development, Channel & Alliances, and other technical specialists to deliver transformative, AI-powered DevSecOps solutions.
• Shape the future of software development by crafting innovative solutions that align GitLab's platform with customers' long-term vision, compliance needs, and business objectives.
• Build deep, strategic partnerships by mastering your customers' industry landscape, success metrics, and growth trajectories so you can position GitLab as their indispensable technology ally.
• Design and execute strategic account plans, including opportunity mapping, stakeholder alignment, and multi-threaded engagement, to expand GitLab usage within new and existing strategic accounts.
• Lead end-to-end customer journeys from initial discovery through evaluation, negotiation, and successful implementation, ensuring a consistent, high-quality experience at every stage of the sales cycle.
• Champion continuous improvement by contributing to forecasting and pipeline reviews, conducting sophisticated win/loss analyses, and sharing strategic insights that refine our go-to-market approach.
• Prepare and deliver compelling customer-facing and internal presentations, proposals, and recommendations that clearly communicate value, business outcomes, and the path to long-term partnership with GitLab.

What you'll bring

• Experience driving complex B2B software sales cycles with enterprise customers, ideally in DevSecOps, software development tools, or adjacent SaaS solutions.
• Background selling into large, enterprise accounts in Chicago, United States, with the ability to build trusted C-level and senior stakeholder relationships across business and technical teams.
• Knowledge of Chicago enterprise market, including key industries, buying centers, and decision-making dynamics, with the ability to build and nurture a relevant professional network.
• Ability to drive new business acquisition and expansion within enterprise accounts through consultative, multi-stakeholder sales motions that lead to sustainable, long-term customer partnerships.
• Experience collaborating with channel and strategic partners to generate pipeline, co-sell, and support successful customer adoption.
• Effective communication and interpersonal skills, with the ability to lead account strategy, influence internal and external stakeholders, and remain calm under pressure.
• Ability to work in line with GitLab's values, use GitLab and Salesforce in your daily work, and travel as needed while following company travel policies.

About the team

The Enterprise Sales team is responsible for driving growth, adoption, and long-term value for GitLab's AI-powered DevSecOps platform with our largest and most strategic customers. As a Strategic Account Executive focused on Chicago, you'll be part of a distributed, all-remote team that works asynchronously across regions and partners closely with GitLab's sales engineering, marketing, and customer success teams. We value transparency, collaboration, and a consultative approach, and we support one another through shared account planning, regular deal reviews, and knowledge sharing focused on enterprise customers across the Chicago region.