Director, Customer Experience Strategy

Gitlab

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.

Calendly

WHAT’S IN IT FOR YOU?  Ready to make a serious impact? Millions of people already rely on Calendly, and we’re still in the midst of exciting product growth — it’s a fantastic time to join us. Everything you’ll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you’ve ever worked with, then we hope you’ll consider allowing Calendly to be a part of your professional journey. A DAY IN THE LIFE You’ll report to the Director of Analytics and serve as the connective tissue across Calendly’s Analytics organization. Our teams generate valuable insights across Product Analytics, Reporting Analytics, Marketing Analytics, and Data Science. But insights only create value when they influence decisions. This role exists to bridge the gap between analytical output and business action. You’ll partner closely with analysts, analytics leaders, and business stakeholders to understand the underlying drivers behind findings, connect patterns that may not be visible within a single team or analysis, and identify the most important implications for the business. You’ll help determine what matters, why it matters, and what actions leaders should consider as a result. You are not responsible for conducting analyses yourself. Instead, you’ll synthesize findings across the organization, connect them to broader business strategy and performance, and ensure they are communicated in ways that drive understanding, alignment, and action. This is not a reporting or dashboarding role. It is a strategic synthesis, storytelling, and influence role focused on increasing the visibility, usability, and business impact of Calendly’s analytics investments. ON A TYPICAL DAY, YOU’LL: * Partner with Analytics teams and business leaders to understand emerging trends, identify the most important business implications, and shape narratives around high-impact findings. * Synthesize insights across Product Analytics, Reporting Analytics, Marketing Analytics, and Data Science, connecting findings to broader business strategy, customer behavior, product performance, and company goals. * Create executive-ready communications including decision briefs, presentations, strategic memos, planning materials, and leadership updates. * Curate and maintain recurring insight communications, including weekly and monthly business reviews, executive summaries, and stakeholder updates. * Ensure critical insights reach the right audiences—from the board and executive team to functional leaders and the broader organization—in formats that drive alignment and decision-making. * Develop foundational materials that improve organizational understanding of key business drivers, metrics, customer behaviors, and strategic priorities. * Establish standards and best practices for analytics storytelling, insight packaging, discoverability, and communication quality across the Analytics organization. * Help Analytics teams leverage AI and emerging tools to scale communications while maintaining editorial quality and analytical rigor. WHAT DO WE NEED FROM YOU? BASIC QUALIFICATIONS * 8+ years of experience in strategy, business operations, consulting, analytics enablement, product operations, research synthesis, or similar roles that translate complex information into business decisions. * Exceptional written and verbal communication skills, with the ability to simplify complex concepts without losing nuance and adapt messaging for audiences ranging from individual contributors to executive leadership. * Strong business acumen and analytical curiosity, with the ability to engage deeply with analytical findings, identify the most important insights, and connect them to broader company strategy, customer behavior, and business performance. * Demonstrated experience creating executive-level narratives, recommendations, and decision-support materials from analytical, technical, or operational inputs. * Experience working cross-functionally with analytics, product, GTM, finance, operations, and executive stakeholders. * Strong organizational and prioritization skills, with the ability to manage multiple concurrent projects and stakeholders. * High degree of ownership and comfort operating in ambiguous, fast-changing environments. PREFERRED QUALIFICATIONS * Experience in management consulting, business strategy, chief of staff, business operations, analytics leadership, or similar strategic roles. * Experience supporting executive leadership teams, strategic planning processes, board reviews, or company-level business reviews. * Familiarity with analytics workflows, experimentation, metrics, forecasting, and data-informed decision-making environments. * Track record of increasing the visibility, adoption, and business impact of analytical work across multiple functions. * Familiarity with AI tools for content creation and knowledge management, including appropriate use cases and quality controls. This role may require occasional travel for company events, team collaboration, or offsites. Tier 1 Salary Hiring Range $173,027—$203,561 USD Tier 2 Salary Hiring Range $158,608—$186,597 USD Tier 3 Salary Hiring Range $144,189—$169,634 USD The ranges listed above are the expected annual base salary for this role, subject to change. Calendly takes a number of factors into consideration when determining an employee’s starting salary, including relevant experience, relevant skills sets, interview performance, location/metropolitan area, and internal pay equity. Base salary is just one component of Calendly’s total rewards package. All full-time (30 hours/week) employees are also eligible for our Top Performer Bonus program (or Sales incentive), equity awards, and competitive benefits. Calendly uses the zip code of an employee’s remote work location, or the onsite building location if hybrid, to determine which metropolitan pay range we use. Current geographic zones are as follows: * Tier 1: San Francisco, CA, San Jose, CA, New York City, NY * Tier 2: Chicago, IL, Austin, TX, Denver, CO, Boston, MA, Washington D.C., Philadelphia, PA, Portland, OR, Seattle, WA, Miami, FL, and all other cities in CA. * Tier 3: All other locations not in Tier 1 or Tier 2 If you are an individual with a disability and would like to request a reasonable accommodation as part of the application or recruiting process, please let your Recruiter know when first connecting with them. Calendly is registered as an employer in many, but not all, states. If you are located in Alaska, Delaware, Hawaii, Idaho, Iowa, Montana, Nebraska, North Dakota, Rhode Island, South Dakota, and West Virginia, you will not be eligible for employment. Note that all individual roles will specify location eligibility. All candidates can find our Candidate Privacy Statement here Candidates residing in California may visit our Notice at Collection for California Candidates here: Notice at Collection This role may require occasional travel for company events, team collaboration, or offsites.

Gitlab

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 Director, Pipeline Excellence you'll help GitLab build a predictable, efficient, and scalable pipeline engine across our go-to-market motions. You'll own pipeline strategy, the operating cadence, and performance improvement work so we can consistently meet pipeline and revenue goals. You'll partner with sales, marketing, sales development, customer success, finance, and analytics to align multi-quarter targets and investments, codify global operating standards, and improve funnel conversion and velocity across inbound, outbound, partner, and expansion. In your first year, you'll strengthen the 13-week Revenue Operating Cadence for pipeline, establish clear pipeline definitions and hygiene standards, and deliver reporting and insights that improve execution quality, forecast accuracy, and decision-making. It's a unique opportunity to shape how GitLab plans, generates, and converts pipeline at scale in a remote, globally distributed environment. WHAT YOU’LL DO * Lead GitLab's end-to-end pipeline growth strategy and multi-quarter target-setting across regions, segments, and routes-to-market (inbound, outbound, partner, and expansion), including capacity planning and program mix decisions. * Translate top-down revenue and coverage goals into bottom-up pipeline targets, capacity plans, and the channel and program mix, in partnership with sales, marketing, and finance. * Design, run, and continuously improve GitLab's pipeline operating rhythm anchored in the 13-week Revenue Operating Cadence, including pipeline reviews, pipeline council, sales plays, and executive updates aligned to monthly and quarterly forecasting milestones. * Own the design and execution of pipeline generation programs, including codified sales plays and pipeline generation days every other week, ensuring alignment to annual operating plan targets and coverage needs. * Define and enforce global pipeline operating standards across the funnel (lead to opportunity to closed-won), including qualification standards, handoffs, service level agreements (SLAs), routing logic, and stage definitions. * Build and maintain a clear pipeline taxonomy (source, type, motion, segment) and a shared glossary for pipeline metrics to ensure consistent reporting and decision-making. * Establish pipeline hygiene standards and checkpoints (weekly, monthly, and quarterly) to improve data quality, forecast accuracy, and execution consistency across go-to-market teams. * Deliver pipeline analytics, dashboards, and funnel diagnostics (coverage, creation, conversion, velocity, quality, and pipeline at risk), and provide clear recommendations on where to invest to hit pipeline and revenue goals. WHAT YOU’LL BRING * Deep experience in revenue operations, sales operations, marketing operations, or related go-to-market strategy and operations roles, with significant ownership of pipeline and funnel management in B2B SaaS. * Ability to navigate and influence complex, cross-functional organizations, balancing the needs of sales, marketing, sales development, customer success, finance, and analytics while operating effectively in ambiguity. * Proven director-level leadership skills, including experience managing, mentoring, and developing high-performing operations and analytics teams. * Strong understanding of end-to-end go-to-market funnels across inbound, outbound, partner, and expansion motions, and how pipeline coverage, conversion, velocity, and quality translate to revenue outcomes. * Excellent analytical and communication skills, including comfort turning data into clear recommendations and influencing senior go-to-market and finance leaders through concise narratives and decision support. * Experience designing and running operating cadences and governance for pipeline performance (including forecasting milestones, pipeline reviews, and hygiene checkpoints) with clear owners, inputs, outputs, and decisions. * Ability to define, document, and drive adoption of standardized process and data definitions (for example, pipeline taxonomy, stages, service level agreements (SLAs), and hygiene standards) across systems and teams. * Capacity to work autonomously and asynchronously in a fully remote environment while staying aligned to shared goals, processes, and priorities across the broader GitLab team. * Familiarity with customer relationship management (CRM) and business intelligence (BI) tools (for example, Salesforce for CRM and Looker or Tableau for BI) to build dashboards, metrics frameworks, and self-serve reporting for pipeline and funnel performance.   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 $168,000—$285,600 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.