About this role.
This mid-senior AI transformation role owns the CRO field organization’s AI agenda, spanning enablement strategy, high-value use cases, operational scaling, adoption measurement, and governance. The hire will translate field needs into technical requirements while partnering with product, engineering, enablement, and operations teams. Core deliverables include a prioritized AI enablement roadmap, scalable workflows for successful pilots, a field-champion network, and safe AI adoption standards. The role requires substantial independent judgment, strong GTM enablement or sales-operations experience, and practical business deployment experience with AI tools. It is a remote US position reporting to the VP of Enablement & AI.
Role DNA
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Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
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Core skills
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Sample interview questions
I would explain the business problem, stakeholder group, and baseline metrics first. I would then describe how I prioritized the use case, piloted a solution with a defined user cohort, measured adoption and business impact, incorporated feedback, and documented a repeatable rollout process with training, governance, and ongoing performance monitoring.
I would use a transparent scoring model that weighs expected business impact, user reach, feasibility, data readiness, risk, implementation effort, and alignment with company strategy. I would start with practical, measurable workflows such as prospecting support, content generation, or call intelligence, then use pilot results to determine which initiatives should scale.
I would involve end users and field champions early, embed tools into existing workflows, define clear role-based use cases, and provide lightweight enablement at the point of need. I would track usage, proficiency, behavior change, and business outcomes, then use the findings to improve the experience and remove operational barriers.
I would establish a practical governance process covering approved tools, data classification and handling, security and privacy review, vendor vetting, human oversight, and escalation paths. The goal would be to protect customer and company data while making compliant adoption easy enough that field teams do not bypass the approved process.
I translate field feedback into concise problem statements, user journeys, measurable requirements, and prioritized tradeoffs rather than jumping immediately to a solution. I maintain a regular feedback loop during pilots so technical teams understand real user behavior, while field stakeholders receive clear expectations about scope, timelines, and constraints.
GitLab is the intelligent orchestration platform for DevSecOps. GitLab enables organizations to increase developer productivity, improve operational efficiency, reduce security and compliance risk, and accelerate digital transformation. More than 50 million registered users and more than 50% of the Fortune 100* trust GitLab to ship better, more secure software faster.
The same principles built into our products are reflected in how our team works: we embrace AI as a core productivity multiplier, with all team members expected to incorporate AI into their daily workflows to drive efficiency, innovation, and impact. GitLab is where careers accelerate, innovation flourishes, and every voice is valued. Our high-performance culture is driven by our values and continuous knowledge exchange, enabling our team members to reach their full potential while collaborating with industry leaders to solve complex problems. Co-create the future with us as we build technology that transforms how the world develops software.
*Fortune 500® is a registered trademark of Fortune Media IP Limited, used under license. Claim based on GitLab data. Fortune 100 refers to the top 20% ranked companies in the 2025 Fortune 500 list, published in June 2025. Fortune and Fortune Media IP Limited are not affiliated with, and do not endorse products or services of GitLab.
An overview of this role
The AI Transformation Owner drives the end-to-end AI agenda for the field organization, translating emerging AI capabilities into concrete enablement roadmaps, field use cases, and org-level strategy. You will partner closely with product and engineering teams to pilot and scale AI solutions, own the operational transformation plan needed to embed AI into day-to-day field workflows, and establish the governance framework that keeps AI adoption safe, compliant, and aligned with company standards. This is a hands-on role for someone who can move from strategy to execution without heavy oversight.
This role reports to the Vice President, Enablement & AI.
What You’ll Do
- AI Enablement Roadmap: Own and continuously evolve the roadmap for AI-driven enablement initiatives, prioritizing based on field impact, feasibility, and alignment with broader Enterprise AI team and strategy..
- AI Field Use Cases: Identify, scope, and execute on high-value AI use cases for the field (e.g., deal support, prospecting, content generation, guided selling, skills, change management), working with stakeholders to define success criteria and measure impact.
- AI Field Champions: build relationships with champions in the field organization to activate power-usage and drive peer-led adoption; track this adoption (e.g., usage, proficiency, behavior change) with our AI Ops Specialist and Enablement Analyst.
- Ops Transformation Plan: Design and drive the operational plan that turns AI pilots into scaled, repeatable processes, coordinating across enablement, ops, and technical teams to remove execution bottlenecks.
- AI Governance: Influence and lead governance standards for AI tool adoption in the field, including data usage, risk review, tool vetting, and alignment with company-wide AI policy.
What You’ll Bring
- Mid-Senior Experience: Several years of experience in enablement, sales operations, or a related GTM function, with a track record of owning initiatives end-to-end.
- AI Solutions Experience: Direct experience evaluating, piloting, or deploying AI tools or solutions in a business context, with a solid technical understanding of how they work and where they add value. Act as the field’s primary advocate for AI tools (e.g., AI-assisted prospecting, call intelligence, forecasting copilots, RFP/proposal generation).
- Cross-Functional Fluency: Proven ability to work closely with product and engineering teams, translating field needs into technical requirements and vice versa.
- Self-Sufficiency: Comfortable operating with significant autonomy — able to define scope, structure ambiguous problems, and drive work forward without needing detailed direction.
- Organization & Execution: Strong project management instincts; able to manage multiple workstreams (roadmap, use cases, ops transformation, governance) in parallel without dropping details.
- Innovative Mindset: A builder’s orientation toward new technology — curious about what’s possible, willing to experiment, and able to separate genuine opportunity from hype.
- Enablement/Sales Background: Familiarity with field or sales enablement motions (onboarding, tool adoption, content, coaching) and how AI can realistically augment them.
- GitLab Values Alignment: Ability to work in an all-remote, asynchronous environment, leaning heavily on transparency and collaboration as defined in the GitLab Handbook.
About the team
The Enablement & AI function is part of the CRO organization. Enablement is instrumental in helping GitLab grow at a more accelerated pace and achieve our ambitious revenue targets. The enablement organization comprises enablement leads serving the CRO business functions, a centralized content group, AI tech resources, and an operations team.
How GitLab will support you
- Benefits to support your health, finances, and well-being
- Flexible Paid Time Off
- Team Member Resource Groups
- Equity Compensation & Employee Stock Purchase Plan
- Growth and Development Fund
- Parental leave
- Home office support
Please note that we welcome interest from candidates with varying levels of experience; many successful candidates do not meet every single requirement. Additionally, studies have shown that people from underrepresented groups are less likely to apply to a job unless they meet every single qualification. If you’re excited about this role, please apply and allow our recruiters to assess your application.
The base salary range for this role’s listed level is currently for residents of the United States only. This range is intended to reflect the role’s base salary rate in locations throughout the US. Grade level and salary ranges are determined through interviews and a review of education, experience, knowledge, skills, abilities of the applicant, equity with other team members, alignment with market data, and geographic location. The base salary range does not include any bonuses, equity, or benefits. See more information on our benefits and equity. Sales roles are also eligible for incentive pay targeted at up to 100% of the offered base salary.
United States Salary Range
$139,200—$235,200 USD
How GitLab Supports Full-Time Employees
- Benefits to support your health, finances, and well-being
- Flexible Paid Time Off
- Team Member Resource Groups
- Equity Compensation & Employee Stock Purchase Plan
- Growth and Development Fund
- Parental Leave
Please note that we welcome interest from candidates with varying levels of experience; many successful candidates do not meet every single requirement. Additionally, studies have shown that people from underrepresented groups are less likely to apply to a job unless they meet every single qualification. If you’re excited about this role, please apply and allow our recruiters to assess your application.
Country Hiring Guidelines: GitLab hires new team members in countries around the world. All of our roles are remote, however some roles may carry specific location-based eligibility requirements. Our Talent Acquisition team can help answer any questions about location after starting the recruiting process.
Privacy Policy: Please review our Recruitment Privacy Policy. Your privacy is important to us.
GitLab is proud to be an equal opportunity workplace and is an affirmative action employer. GitLab’s policies and practices relating to recruitment, employment, career development and advancement, promotion, and retirement are based solely on merit, regardless of race, color, religion, ancestry, sex (including pregnancy, lactation, sexual orientation, gender identity, or gender expression), national origin, age, citizenship, marital status, mental or physical disability, genetic information (including family medical history), discharge status from the military, protected veteran status (which includes disabled veterans, recently separated veterans, active duty wartime or campaign badge veterans, and Armed Forces service medal veterans), or any other basis protected by law. GitLab will not tolerate discrimination or harassment based on any of these characteristics. See also GitLab’s EEO Policy and EEO is the Law. If you have a disability or special need that requires accommodation, please let us know during the recruiting process.
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