Director, Deal Desk

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 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. WHAT YOU'LL DO * 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. WHAT YOU'LL BRING * 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.  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 $203,200—$345,600 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.

WHAT DO WE DO? Paddle offers digital product companies a completely different approach to their payment infrastructure. Instead of assembling and maintaining a complex stack of payments-related apps and services, we're a Merchant of Record for our customers. That means we take away 100% of the pain of payment fragmentation. It's faster, safer, cheaper, and, above all, way better. We're backed by investors including KKR, FTV Capital, Kindred, Notion, and 83North and serve over 6000 software sellers in 245 territories globally. THE ROLE: We're looking for a sharp, commercially-minded Director of FP&A to lead the FP&A function at Paddle and drive performance across revenue growth, cost discipline, and analysis to inform and guide capital allocation decisions. Reporting directly to our VP of Finance, you'll serve as the connective tissue between finance and the broader leadership team. You'll own the rhythm by which Paddle plans, forecasts, and a key influencer on business decisions. This is an exciting moment to join: we've intentionally paused to redesign how FP&A operates at Paddle, and we're building for the next chapter of growth. WHAT YOU'LL DO * Build and develop the FP&A team, providing clear direction, regular coaching and development opportunities and hiring to scale capacity in line with business needs * Partner with GTM, Product & Engineering, and functional leaders to build investment cases, surface unit economics insights, and embed finance as a performance partner in business decisions, including on deal desk decisions, commission plans design, and partnership opportunities. * Co-author board and CFO/CEO materials, translating complex financial data into clear narratives on revenue, cost, and capital allocation * Lead Paddle's end-to-end planning cycle — from the annual budget, monthly forecasts, and long-range plans in Pigment * Own and advance the Pigment platform, acting as product lead to drive more effectiveness from our streamline our 3-statement forecasting, revenue planning, and reporting structures. * Drive the Monthly Business Review and QBR cadences: producing standardised packs, facilitating cross-functional discussions, and ensuring leadership leaves each session with clear prioritised actions WE'D LOVE TO HEAR FROM YOU IF YOU * Have significant FP&A leadership experience in a high-growth marketplace, SaaS or technology business * Have a track record of building or transforming an FP&A function into a function that is business impact driven, vs. merely producing reporting oriented. * Are a confident business partner who can operate across all levels — from C-suite to VPs and functional directors — translating financial insight into decisions that move the business * Are a systems oriented thinker, that is wired to optimize the recurring work, that will enable more of the team’s time spent on project-work that drives business impact. * A history of effective use and progressive development of modern planning platforms (Pigment preferred) and can own tooling as a product, not just in a “maintenance” role. * Bring commercial instincts alongside technical rigour — you're as comfortable being the architect for complex revenue cohort models that your team will build, while at the same time being able to synthesise implications of that modelling to business leaders to help guide investment decisions to support growth * Have led a full annual planning cycle end-to-end, including budgeting, forecasting, consolidation, and board reporting EVERYONE IS WELCOME AT PADDLE At Paddle, we're committed to removing invisible barriers, both for our customers and within our own teams. We recognise and celebrate that every Paddler is unique and we welcome every individual perspective. As an inclusive employer, we don't care if, or where, you studied, what you look like or where you're from. We're more interested in your craft, curiosity, passion for learning and what you'll add to our culture. We encourage you to apply even if you don't match every part of the job ad, especially if you're part of an underrepresented group. Please let us know if there's anything we can do to better support you through the application process and in the workplace. We will do everything we can to support any accommodations needed. We're committed to building a diverse team where everyone feels safe to be their authentic self. Let's grow together. WHY YOU'LL LOVE WORKING AT PADDLE We are a diverse, growing group of Paddlers across the globe who pride ourselves on our transparent, collaborative and respectful culture. We live and breathe our values, which are: Paddle for others Paddle together Paddle simply We offer a full suite of benefits, including attractive salaries, stock options, retirement plans, private healthcare and well-being initiatives. We are a 'digital-first' company, which means you can work remotely, from one of our stylish hubs, or even a bit of both! We offer all team members unlimited holidays and enhanced parental leave. We invest in learning and will help you with your personal development via constant exposure to new challenges, an annual learning fund, and regular internal and external training.