Senior Director, Deal Desk

GitLab

11h•$203,200 - $345,600•Remote

About The Position

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.

Requirements

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.

Responsibilities

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.