Director of Engineering, Growth & Monetization

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 Director of Engineering, Security Factory, you will lead the engineering organization responsible for GitLab’s customer-facing security capabilities across our AI-powered DevSecOps platform. You’ll help shape how customers detect, prioritize, and remediate vulnerabilities across modern software workflows by guiding teams that build proprietary scanners, AI-driven detection engines, agentic remediation flows, and supporting security foundations. Reporting to the VP of Engineering, Sec section, you’ll set the engineering vision and roadmap for a distributed group of nine teams, including engineering managers, and create the conditions for strong delivery, sound technical direction, and healthy team growth. Some examples of our projects: * Advanced proprietary scanners for Static Application Security Testing, Software Composition Analysis, Secret Detection, and related AI and machine learning detection engines * Agentic security flows for autofix and guided remediation, plus research that strengthens AI security, threat intelligence, vulnerability management, and security foundations WHAT YOU’LL DO * Set the engineering vision and multi-quarter roadmap across teams working on proprietary scanners, AI-driven security workflows, research functions, vulnerability management, and security foundations. * Lead a distributed engineering organization of managers and individual contributors, with a focus on team performance, engagement, and career development. * Drive architectural decisions for AI and machine learning detection engines, agentic remediation flows, and scalable scanning infrastructure. * Partner with product management to define priorities, shape requirements, and deliver security capabilities for customers in regulated and security-conscious environments. * Own the engineering delivery of GitLab’s proprietary application security scanners, agentic remediation workflows, and AI Security Research efforts. * Represent the Security Factory stage in cross-functional planning, executive reviews, security disclosures, and customer conversations. * Establish engineering standards for delivery, observability, incident response, scanner quality, and code quality. * Contribute to GitLab’s transparent, async-first way of working through issues, merge requests, and the GitLab handbook. WHAT YOU’LL BRING * Experience leading engineering organizations with multiple teams and managers in a distributed environment. * Strong understanding of application security fundamentals, including Static Application Security Testing, Software Composition Analysis, secret detection, vulnerability management workflows, and software supply chain security. * Experience building detection, analysis, or scanning systems in a software as a service or DevSecOps environment, including trade-offs across precision, recall, latency, and scale. * Direct experience shipping a customer-facing AI or machine learning product feature tied to detection or remediation quality outcomes. * Ability to partner closely with product management on roadmap planning, prioritization, and requirements in a product-led context. * Strong written communication skills and comfort leading through clear documentation in a remote, async-first organization. * Collaborative leadership style that supports teams, gives direct feedback, and aligns with GitLab’s values. * Familiarity with agentic AI systems, AI agent orchestration, threat intelligence research, or open source security tooling is useful, and we welcome candidates with adjacent or transferable experience. ABOUT THE TEAM The Security Factory group builds the customer-facing security capabilities of GitLab’s AI-powered DevSecOps platform. The organization includes nine teams working across proprietary scanners, AI-driven detection, agentic remediation, research, vulnerability management, and security foundations, and it collaborates asynchronously across regions with product management and other cross-functional partners. The team is focused on improving detection quality, scaling security workflows for enterprise use, and strengthening how GitLab helps customers secure the software supply chain. For more on how this team works, see the Sec Engineering Handbook page.  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.

Toast

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. As the Director of Engineering for Retail, you will be the primary technical owner of Toast’s highest-growth business unit - a $50M+ "startup" currently doubling year-over-year. We’re bringing the same all-in-one platform beloved by restaurants to a whole new segment of businesses. You are responsible for building a delightful, flexible, and scalable platform that serves the unique needs of businesses across a wide variety of retail personas. You will own everything from agentic inventory automation, to optimizing the POS for high-throughput checkout experiences, and everything in between. A DAY IN THE LIFE (RESPONSIBILITIES) * Own the Retail Technical Strategy: Mandate to move beyond siloed feature development to build a unified, extensible retail core that supports a wide variety of retail personas at scale * Architect for Resilience: Ensure high availability and blazing fast performance at the edge; you will oversee the infrastructure that keeps our high-volume retailers up and running regardless of connectivity * Deploy Autonomous Systems: Lead the move from manual and labor-intensive inventory management to AI-driven autonomous systems, saving hours of time and unlocking new operational efficiencies for thousands of customers * Raise Talent Density: Uplevel the engineering organization by identifying and attracting top-tier talent and coaching existing managers to operate as high-autonomy owners * Own the Outcome: Partner with Product and Design to drive the P&L of the Retail business, managing the immediate delivery of the Retail POS and Purchasing & Receiving squads while developing a long-term strategy for the Grocery persona WHAT YOU'LL NEED TO THRIVE (REQUIREMENTS) * Platform-First Mindset: You have a track record of building configurable platforms rather than just collections of features * Systems Architect Background: Deep experience with distributed systems and edge computing. You know how to build software that is bulletproof in high-pressure, real-world physical environments * High-Growth "Builder" DNA: You have led engineering teams through the "1-to-10" scale phase at a high-growth startup and know how to maintain velocity while increasing technical rigor * Obsession with Data Integrity: Experience solving complex inventory, supply chain, or financial reconciliation problems where data accuracy is the difference between a successful business and a failed audit * Drives Exceptional Outcomes: You hold an incredibly high bar for talent and execution. You are a "leader of leaders" who empowers managers but stays close enough to the metal to spot architectural flaws * Strategic Influence: You can navigate high-stakes cross-functional relationships, moving beyond "feature requests" to influence the fundamental business strategy through technical innovation AI at Toast At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture. Our Total Rewards Philosophy  We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits. The base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and geographic location. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions if eligible), equity, and benefits. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy. Zone A $283,000—$453,000 USD Zone B $246,000—$394,000 USD Zone C $222,000—$355,000 USD How Toast Uses AI in its Hiring Process Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. To learn more: https://careers.toasttab.com/ai-in-hiring Our Approach to Hybrid Working We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region: https://careers.toasttab.com/locations-toast Diversity, Equity, and Inclusion is Baked into our Recipe for Success At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences. We Thrive Together We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and regionally, check out: https://careers.toasttab.com/locations-toast. Apply today! Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact candidateaccommodations@toasttab.com. ------ For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

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 of Production and Tenant Platform Engineering, you will lead the foundational engineering teams responsible for the reliability, scalability, and lifecycle of the GitLab platform. This role brings together two critical domains: the "Tenant Experience" (the operator and customer facing platform surfaces) and the "Production Engineering" pillars (the underlying infrastructure that powers GitLab.com and our self-managed offerings). You will lead a high-performing organization of managers and engineers who own the entire stack, from network infrastructure, fleet management, and cloud cost efficiency to observability, tenant controls, and the upgrade lifecycle. Your mission is to evolve GitLab’s platform architecture to support massive scale across SaaS, Dedicated, and self-managed environments, ensuring that whether a customer runs in the cloud or on-prem, they experience a platform that is reliable, performant, and easy to operate. This is a high-impact leadership role. You’ll define the strategy for how GitLab remains resilient, manage critical production incidents, drive cloud efficiency, and build the abstractions that allow modular services (like AI Gateway, ClickHouse, and OpenBao) to ship and scale with confidence. You will succeed by cultivating a culture of operational excellence, simplifying complex technical architectures, and ensuring your organization operates with clarity and alignment in a high-growth environment. What you'll do * Lead a Unified Platform Strategy: Define and execute a cohesive roadmap that aligns Production Engineering (Fleet, Network, Cost, Responder) with Tenant Experience (Observability, Controls, Upgrade Tooling). Ensure these investments connect cleanly to support GitLab’s multi-tenant and self-managed reality. * Drive Operational Excellence & Reliability: Maintain deep accountability for GitLab’s production outcomes. You will oversee incident management, alert efficacy, and service-level reliability, ensuring that both GitLab.com and our global customer base benefit from a stable, high-performance platform. * Scale Engineering Leadership: Manage a senior management team, coaching them on performance, hiring, team structure, and execution. You will create the organizational conditions for success—defining clear mandates, removing blockers, and fostering a culture of ownership and accountability. * Evolve the Platform Architecture: Guide the technical evolution of the platform. This includes optimizing fleet management and cloud utilization, maturing our observability and self-healing frameworks, and delivering a modern upgrade experience that bridges the gap between legacy Omnibus and modern Kubernetes/cloud-native models. * Cross-Functional Partnership: Collaborate with Engineering Directors, Product Leaders, and Reliability/Delivery teams to ensure platform investments align with business priorities (e.g., AI roadmap, cost goals, deployment speed). * Translate Strategy into Execution: Convert broad organizational goals into actionable roadmaps. You will make tough trade-off decisions between immediate production stability and long-term architectural health, ensuring the team remains focused on outcomes that drive business value. * Build the Future of GitLab Operations: Champion initiatives that reduce operational toil, improve the developer/operator experience, and standardise platform interfaces across our modular service architecture. What you'll bring * Executive Engineering Leadership: Proven experience leading large, distributed engineering organizations (managing managers) within complex, high-scale platform environments. * Deep Production Expertise: A track record of owning critical production systems. You understand the realities of running distributed systems at scale, including incident response, traffic management, capacity planning, and cloud infrastructure costs. * Platform Engineering Acumen: Deep familiarity with large-scale distributed systems, along with various delivery models including containerized and Kubernetes-based platforms, infrastructure-as-code, and the operational challenges of supporting multi-tenant SaaS alongside diverse self-managed (Omnibus/OAK) deployments. * Strategic Architectural Judgment: Ability to evaluate complex technical trade-offs—such as build vs. buy, cloud-first vs. on-prem constraints, and architectural patterns for modular services—and provide clear, defensible direction. * Change Management: Experience leading teams through periods of significant growth, organizational change, or technical pivot (e.g., modernizing a monolith or scaling infrastructure for new product lines). * Commitment to GitLab Values: Strong alignment with our values of ownership, speed with quality, and customer outcomes. * Operational Focus: A proven ability to raise the bar on production quality. You have successfully led initiatives that measurably improved system reliability, reduced toil, or optimized infrastructure efficiency. About the team The Production and Tenant Platform team sits at the core of GitLab’s Infrastructure Platforms organization. We own the "how" of GitLab—how it runs, how it scales, and how it is managed by operators and customers alike. Our scope is broad: we manage the network edge, the underlying cloud compute fleet, and the cost efficiency of our services; we provide the observability signals that detect issues; we define the tenant controls (rate limits, feature flags) that protect our system; and we build the upgrade tools that make GitLab’s release cycle sustainable. We work across all GitLab environments (GitLab.com, Dedicated, and self-managed) to deliver a unified, coherent platform. We are a team of problem-solvers who value transparency and autonomy, and we partner closely with Delivery, Dedicated, and Product teams to ensure the infrastructure isn't just reliable, but that it is the primary engine of GitLab's growth and customer success. 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.