Senior Director, Deal Desk

As the Senior Director, Deal Desk, you will lead GitLab's global Deal Desk organization and help evolve it from a strong quote-to-cash control point into a strategic commercial capability that helps GitLab structure, approve, operationalize, and win complex subscription and consumption-based deals at scale. You will oversee the global approach to deal structure, bookings reconciliations, and Salesforce bookings fidelity, while serving as a trusted partner to Sales and Finance leaders.

In this role, you will help define how GitLab brings newer pricing and packaging models to market, including usage-based and hybrid motions, while keeping commercial processes simple, scalable, auditable, and aligned to GitLab's value-based pricing philosophy. You will work across Sales, Finance, Product, Pricing, Legal, Sales Operations, Enterprise Applications, Fulfillment, and Customer Experience to set commercial guardrails, approvals, systems requirements, and field enablement that support GitLab's transition toward a consumption-first go-to-market model.

This is a high-impact leadership opportunity for someone who can connect commercial strategy with operational execution. In your first year, you will shape how GitLab supports complex deals globally, improve consistency across processes and systems, and strengthen the operating model that enables the field to move faster without compromising policy, margin, or customer experience.

• →Lead the global Deal Desk organization, including managers and regional teams, and own the hiring, enablement, operating rhythm, and ongoing evolution of the function.
• →Own the end-to-end service model for Deal Desk and Order Management, ensuring the team can support increasing deal complexity while maintaining speed, consistency, and control.
• →Serve as the executive escalation point for complex, non-standard, and strategic transactions, balancing customer needs, deal velocity, pricing discipline, and operational integrity.
• →Own the commercial operating model for consumption-priced and hybrid offers, including standard deal patterns, approval thresholds, exception paths, and field guidance for non-standard structures.
• →Partner with Product and Pricing to translate pricing and packaging strategy into executable commercial rules, approval matrices, quoting workflows, and systems requirements for new products, bundles, and monetization changes.
• →Define guardrails for multi-year agreements, ramps, bundled offers, usage-based constructs, private offers, channel motions, and other complex commercial terms so they can be supported without creating downstream billing, fulfillment, or accounting risk.
• →Own global bookings fidelity and reconciliations, including Salesforce bookings accuracy, quote quality, and policy compliance across the quote-to-cash lifecycle.
• →Partner with Sales Operations, Enterprise Applications, Finance, Accounting, Audit, and Compliance teams to improve workflows, strengthen controls, increase automation, and ensure commercial decisions can be operationalized cleanly in downstream systems and processes.

• Significant leadership experience in Deal Desk, Pricing Strategy, Revenue Operations, Sales Operations, Finance Operations, or a closely related quote-to-cash function within enterprise software.
• Proven success leading global or multi-region teams that support complex sales motions, high-growth environments, and cross-functional stakeholders.
• Deep understanding of software pricing models, including per-user, tiered, multi-year, usage-based, and hybrid pricing, with the ability to convert pricing strategy into scalable commercial policy.
• Strong command of bookings policy, revenue recognition concepts, audit readiness, and compliance requirements in a controlled business environment.
• Fluency with core quote-to-cash systems, including customer relationship management (CRM) and billing platforms such as Salesforce and Zuora, and the ability to partner effectively on systems design and workflow improvements.
• Experience designing or improving approval workflows, escalation paths, service-level expectations, executive deal review processes, and CRM or CPQ-enabled quoting operations.
• Strong commercial judgment across direct, channel, private offer, and other non-standard sales motions, with the ability to navigate ambiguity and make balanced decisions.
• Excellent communication and stakeholder management skills, with the ability to use data to influence senior leaders, align cross-functional teams, and lead through change in a global, all-remote environment.

The Deal Desk team at GitLab helps the business balance speed, control, and a strong customer experience as it scales. As part of this team, you'll lead work that improves commercial processes and helps complex transactions move forward in a consistent, scalable way. As a distributed team, the Deal Desk organization focuses on clear decision-making, strong partnership, and continuous improvement. The work is especially meaningful for leaders who enjoy solving complex commercial and operational problems at a company that is continuing to scale. 

• 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.  

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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.