Director, Enterprise Architecture & Intelligent Automation

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 an AI Engineer at GitLab, you'll help build the foundation for GitLab's transformation into an AI-first company. Reporting to the Director, Enterprise AI, you'll be a hands-on technical leader responsible for delivering internal AI-powered solutions that drive measurable business outcomes. Building fast matters, but it's not enough on its own. This role starts with understanding the real problem: mapping how work moves across teams, tools, and handoffs, identifying the true constraint, and validating whether AI is the right solution before you begin development. From there, you'll take ownership from discovery through deployment, combining strong engineering skills with systems thinking and business understanding. Your initial focus will span Sales, Marketing, and Customer Support, where you will embed AI solutions into key systems and workflows. This role offers the opportunity to shape how GitLab team members work, improve flow across the organization, and help advance our mission in a remote, asynchronous, and values-driven environment. WHAT YOU'LL DO * Diagnose business problems before building solutions. Map workflows, identify constraints, and confirm whether AI is the right intervention. Be prepared to say "this doesn't need AI" when that's the honest answer. * Own AI initiatives end-to-end, from stakeholder discovery and technical design through implementation, deployment, and iteration. * Design, develop, and ship AI-powered solutions quickly, delivering working prototypes in days, not months, with a focus on practical outcomes and measurable business value. * Improve organizational flow by building solutions that reduce bottlenecks, shorten lead times, and increase throughput. Measure success using flow metrics alongside adoption and ROI. * Integrate AI capabilities into existing systems and workflows using APIs, orchestration tools, and modern AI platforms, including GitLab Duo Agent Platform, where appropriate. The right tool wins, whether that's custom code, a platform, or a well-crafted prompt. * Be Customer Zero: leverage and showcase GitLab's AI offerings wherever possible, feeding real-world usage insights back to R&D. * Partner closely with stakeholders across functions to understand the real constraints. Ask the right questions, bridge technical and non-technical perspectives, and align on outcomes before jumping to solutions. * Define and track success through business metrics, flow metrics, and feedback loops that make performance visible and actionable. * Contribute to technical direction by evaluating tools, documenting patterns, and creating reusable foundations that help the team scale its impact. WHAT YOU'LL BRING * A Technologist at Heart - Genuinely invested in technology, the foundational and the cutting-edge in equal measure. You're as energised by a well-designed API integration as you are by the latest foundation model release. You reach for the simplest solution that solves the problem well, rather than forcing new technology when proven approaches would do. AI is a powerful part of your toolkit, but it sits on top of solid engineering fundamentals, not in place of them. * Competent, Confident Coding Skills - You can build working solutions end-to-end, write clean and maintainable code, and debug effectively. Whether your skills were honed in a traditional engineering role, through building automations, or shipping side projects, what matters is that you can deliver production-quality work independently. * AI & LLM Technical Depth - Strong proficiency in at least one modern scripting language (Python, JavaScript/TypeScript, or similar) and a solid understanding of REST APIs, GraphQL, and integration patterns. Deep, practical experience with modern AI technologies, specifically: Prompt engineering as a core discipline: designing effective system prompts, managing context windows, structuring multi-turn interactions, evaluating output quality, and iterating systematically on prompt design. * Model selection and cost-performance trade-offs: understanding when a smaller fine-tuned model outperforms a general-purpose large one, when RAG is the right architecture versus expanding the context window, and how to make principled decisions about capability versus cost. * Agentic architecture patterns: tool use, multi-agent orchestration, human-in-the-loop designs, guardrails, evaluation frameworks, and production-grade reliability patterns.Practical fluency across the LLM ecosystem: hands-on experience with models from Anthropic, OpenAI, open-source alternatives, and the judgment to know which to reach for and when. * AI Safety & Risk Awareness - You think critically about how the solutions you build could be exploited, misused, or produce unintended consequences. You know how to design appropriate guardrails (input validation, output filtering, access controls, prompt injection defences, and data leakage prevention) and you treat these as first-class engineering concerns. * Systems Thinking & Diagnostic Rigour - The ability to look at a complex process and see the constraint. Comfortable mapping how work flows end-to-end, identifying bottlenecks, and tracing problems to root causes before proposing solutions. You instinctively ask "what's actually blocking flow here?" before asking "what model should I use?" * Business System Expertise - Familiarity with the landscape of enterprise business systems, CRM (Salesforce), marketing automation (Marketo), support platforms (Zendesk), integration and orchestration tools (Workato), AI platforms (Relevance AI), and enterprise search and knowledge tools (Glean). You don't need deep experience with all of these, but to understand what they do, how they fit together, and be willing to build with and across them. A strong understanding of enterprise data models and workflows is essential. * Broad Functional Understanding - Ability to have meaningful conversations with stakeholders across diverse domains and quickly understand their unique needs. * End-to-End Ownership - Track record of owning complex initiatives from discovery through delivery. Comfortable operating with ambiguity and driving to measurable outcomes independently. * Product Mindset - Ability to scope MVPs, prioritise ruthlessly, and deliver iteratively. In addition, consider adoption, user experience, and business outcomes.   Preferred requirements * Experience with GitLab platform and CI/CD workflows * Background in consulting, solutions engineering, or customer-facing technical roles * Familiarity with value stream mapping, flow metrics, or Theory of Constraints thinking * Experience with low-code/no-code orchestration tools (n8n, Make, Workato) alongside custom development * Previous startup or high-growth company experience * Experience mentoring or leading technical projects with junior engineers ABOUT THE TEAM You will join the Enterprise Technology & AI team. We're the backbone of the organisation, driving transformation in how GitLab team members make decisions, operate at scale, and deliver results for our customers. We believe the best AI solutions start with understanding the system, not the technology. We value people who think in constraints and flow, who build with conviction, and who never stop learning. We work in an all-remote, asynchronous setting, guided by GitLab's values of collaboration, results, efficiency, diversity, inclusion and belonging, iteration, and transparency. 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 $108,400—$129,600 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.

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 a Senior AI Engineer at GitLab, you'll help build the foundation for GitLab's transformation into an AI-first company. Reporting to the Director, Enterprise AI, you'll be a hands-on technical leader responsible for delivering internal AI-powered solutions that drive measurable business outcomes. Building fast matters, but it's not enough on its own. This role starts with understanding the real problem: mapping how work moves across teams, tools, and handoffs, identifying the true constraint, and validating whether AI is the right solution before you begin development. From there, you'll take ownership from discovery through deployment, combining strong engineering skills with systems thinking and business understanding. Your initial focus will span Sales, Marketing, and Customer Support, where you will embed AI solutions into key systems and workflows. This role offers the opportunity to shape how GitLab team members work, improve flow across the organization, and help advance our mission in a remote, asynchronous, and values-driven environment. WHAT YOU'LL DO * Diagnose business problems before building solutions. Map workflows, identify constraints, and confirm whether AI is the right intervention. Be prepared to say "this doesn't need AI" when that's the honest answer. * Own AI initiatives end-to-end, from stakeholder discovery and technical design through implementation, deployment, and iteration. * Design, develop, and ship AI-powered solutions quickly, delivering working prototypes in days, not months, with a focus on practical outcomes and measurable business value. * Improve organizational flow by building solutions that reduce bottlenecks, shorten lead times, and increase throughput. Measure success using flow metrics alongside adoption and ROI. * Integrate AI capabilities into existing systems and workflows using APIs, orchestration tools, and modern AI platforms, including GitLab Duo Agent Platform, where appropriate. The right tool wins, whether that's custom code, a platform, or a well-crafted prompt. * Be Customer Zero: leverage and showcase GitLab's AI offerings wherever possible, feeding real-world usage insights back to R&D. * Partner closely with stakeholders across functions to understand the real constraints. Ask the right questions, bridge technical and non-technical perspectives, and align on outcomes before jumping to solutions. * Define and track success through business metrics, flow metrics, and feedback loops that make performance visible and actionable. * Contribute to technical direction by evaluating tools, documenting patterns, and creating reusable foundations that help the team scale its impact. WHAT YOU'LL BRING * A Technologist at Heart - Genuinely invested in technology, the foundational and the cutting-edge in equal measure. You're as energised by a well-designed API integration as you are by the latest foundation model release. You reach for the simplest solution that solves the problem well, rather than forcing new technology when proven approaches would do. AI is a powerful part of your toolkit, but it sits on top of solid engineering fundamentals, not in place of them. * Competent, Confident Coding Skills - You can build working solutions end-to-end, write clean and maintainable code, and debug effectively. Whether your skills were honed in a traditional engineering role, through building automations, or shipping side projects, what matters is that you can deliver production-quality work independently. * AI & LLM Technical Depth - Strong proficiency in at least one modern scripting language (Python, JavaScript/TypeScript, or similar) and a solid understanding of REST APIs, GraphQL, and integration patterns. Deep, practical experience with modern AI technologies, specifically: Prompt engineering as a core discipline: designing effective system prompts, managing context windows, structuring multi-turn interactions, evaluating output quality, and iterating systematically on prompt design. * Model selection and cost-performance trade-offs: understanding when a smaller fine-tuned model outperforms a general-purpose large one, when RAG is the right architecture versus expanding the context window, and how to make principled decisions about capability versus cost. * Agentic architecture patterns: tool use, multi-agent orchestration, human-in-the-loop designs, guardrails, evaluation frameworks, and production-grade reliability patterns.Practical fluency across the LLM ecosystem: hands-on experience with models from Anthropic, OpenAI, open-source alternatives, and the judgment to know which to reach for and when. * AI Safety & Risk Awareness - You think critically about how the solutions you build could be exploited, misused, or produce unintended consequences. You know how to design appropriate guardrails (input validation, output filtering, access controls, prompt injection defences, and data leakage prevention) and you treat these as first-class engineering concerns. * Systems Thinking & Diagnostic Rigour - The ability to look at a complex process and see the constraint. Comfortable mapping how work flows end-to-end, identifying bottlenecks, and tracing problems to root causes before proposing solutions. You instinctively ask "what's actually blocking flow here?" before asking "what model should I use?" * Business System Expertise - Familiarity with the landscape of enterprise business systems, CRM (Salesforce), marketing automation (Marketo), support platforms (Zendesk), integration and orchestration tools (Workato), AI platforms (Relevance AI), and enterprise search and knowledge tools (Glean). You don't need deep experience with all of these, but to understand what they do, how they fit together, and be willing to build with and across them. A strong understanding of enterprise data models and workflows is essential. * Broad Functional Understanding - Ability to have meaningful conversations with stakeholders across diverse domains and quickly understand their unique needs. * End-to-End Ownership - Track record of owning complex initiatives from discovery through delivery. Comfortable operating with ambiguity and driving to measurable outcomes independently. * Product Mindset - Ability to scope MVPs, prioritise ruthlessly, and deliver iteratively. In addition, consider adoption, user experience, and business outcomes.   Preferred requirements * Experience with GitLab platform and CI/CD workflows * Background in consulting, solutions engineering, or customer-facing technical roles * Familiarity with value stream mapping, flow metrics, or Theory of Constraints thinking * Experience with low-code/no-code orchestration tools (n8n, Make, Workato) alongside custom development * Previous startup or high-growth company experience * Experience mentoring or leading technical projects with junior engineers ABOUT THE TEAM You will join the Enterprise Technology & AI team. We're the backbone of the organisation, driving transformation in how GitLab team members make decisions, operate at scale, and deliver results for our customers. We believe the best AI solutions start with understanding the system, not the technology. We value people who think in constraints and flow, who build with conviction, and who never stop learning. We work in an all-remote, asynchronous setting, guided by GitLab's values of collaboration, results, efficiency, diversity, inclusion and belonging, iteration, and transparency. 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.

Twilio

Who we are  At Twilio, we’re shaping the future of communications, all from the comfort of our homes. We deliver innovative solutions to hundreds of thousands of businesses and empower millions of developers worldwide to craft personalized customer experiences. Our dedication to remote-first work, and strong culture of connection and global inclusion means that no matter your location, you’re part of a vibrant team with diverse experiences making a global impact each day. As we continue to revolutionize how the world interacts, we’re acquiring new skills and experiences that make work feel truly rewarding. Your career at Twilio is in your hands. We use Artificial Intelligence (AI) to help make our hiring process efficient. That said, every hiring decision is made by real Twilions! . See yourself at Twilio Join the team as our next Senior Technical Program Manager, Service Delivery Systems on the GCS Strategy & Operations team. About the job We are looking for a hands-on technical builder to join the GCS Strategy & Operations organization. This role owns the technical foundation that powers how GCS delivers customer outcomes at scale — the intelligent automation, knowledge systems, and decision logic embedded in the service delivery workflows of our Technical Account Management, Professional Services, and Engagement Management teams. You'll design and build systems, including AI workflows that operate within the Customer Experience Operations (CXO) governance model and you'll be accountable to GCS business outcomes: resolution rates, revenue-per-headcount, product adoption and more.   This role sits at the intersection of engineering and program management. You'll write code every week, but your success is measured in GCS outcomes for customers, not a technology roadmap. You'll partner daily with GCS Program Managers, Technical Account Management, Professional Services and Twilio Engineering teams to turn director-level business requirements into reliable, auditable systems. Responsibilities In this role, you’ll: * Architect and build the systems that encode how GCS operates — account health observability, intelligent routing, knowledge retrieval, and workflow automation across our TAM, PS, and EM motions; including cost optimization. * Build AI workflows using the Anthropic Claude API, Claude Agent SDK, and Claude Code, including MCP (Model Context Protocol) servers that connect agents to Slack, Jira, Zendesk, Grafana, Airtable, and internal Twilio systems. * Partner with CXO to design the decision frameworks that determine when systems act autonomously, when humans stay in the loop and own the guardrails — edge cases caught, prompt injection blocked, unintended behaviors prevented — that keep failure rates low. * Extend GCS's observability and analytics foundation with production-quality dashboards and integrations across Grafana (ClickHouse-backed), Salesforce, Tableau, Looker, and Airtable — choosing the right tool for the audience and data source rather than defaulting to one platform. * Operate within CXO's vetting-and-graduation governance model, and help mature it: versioning, evaluation frameworks, A/B testing, and systematic performance measurement across scenarios with GCS specific focus. * Instrument everything you build — retrieval accuracy, action success rates, deflection, and failure patterns — and tie technical performance to GCS outcomes like time to value, resolution rate, cost-per-ticket, and time-to-resolution. * Translate complex system behavior into plain language for director and executive audiences while producing clear technical documentation for the teams who depend on your systems. Qualifications  Twilio values diverse experiences from all kinds of industries, and we encourage everyone who meets the required qualifications to apply. If your career is just starting or hasn't followed a traditional path, don't let that stop you from considering Twilio. We are always looking for people who will bring something new to the table! *Required: * 7+ years of experience building production software or technical systems, in roles such as platform engineering, solutions architecture, or hands-on technical program management. * Production-quality proficiency in Python and/or TypeScript (Node.js), with fluency in REST API integration fundamentals: authentication (OAuth 2.0, API keys, token refresh), webhooks, pagination, rate limiting, error handling and retries, and JSON transformation. * Hands-on experience building AI systems with large language models — tool use / function calling, structured outputs, prompt architecture, and evaluation harnesses — including building and deploying MCP servers to connect enterprise systems. * Deep understanding of how large language models work: how they reason, where they fail, and why. Fluency in RAG architectures, prompt engineering patterns, and agent frameworks. * Advanced SQL, including analytical queries against columnar stores such as ClickHouse. * Dashboard and application development experience across Grafana (data sources, panels, variables, dashboard-as-code, alerting), Salesforce (SOQL, report types, Lightning reports and dashboards), Tableau (data modeling, calculated fields, LOD expressions, publishing to Tableau Cloud or Server), Looker (LookML modeling, Explores, derived tables, publishing to dashboards), and Airtable (base/table design, automations, scripting extensions, API integration) — with the judgment to choose the right tool for a given audience and data source. * Strong engineering practices: Git-based version control, code review, basic CI, and least-privilege patterns when handling customer data. * Demonstrated ability to translate business requirements into system specifications and explain complex technical behavior to non-technical stakeholders. Desired: * Experience embedded in a support or professional services organization, building systems for the teams doing the work. * Experience with Zendesk or similar service platforms, including APIs, triggers, and routing logic. * Experience defining metrics and observability for AI systems in production, and running structured A/B tests or evaluations. * Familiarity with Twilio's products or the CPaaS/SaaS domain. Location This role will be remote, but is not eligible to be hired in San Francisco, CA, Oakland, CA, San Jose, CA, or the surrounding areas. Travel  We prioritize connection and opportunities to build relationships with our customers and each other. For this role, you may be required to travel occasionally to participate in project or team in-person meetings. What We Offer Working at Twilio offers many benefits, including competitive pay, generous time off, ample parental and wellness leave, healthcare, a retirement savings program, and much more. Offerings vary by location. Compensation *Please note this role is open to candidates outside of California, Colorado, Hawaii, Illinois, Maryland, Massachusetts, Minnesota, New Jersey, New York, Vermont, Washington D.C., and Washington State. The information below is provided for candidates hired in those locations only. The estimated pay ranges for this role are as follows: * Based in Colorado, Hawaii, Illinois, Maryland, Massachusetts, Minnesota, Vermont or Washington D.C. : 188,240.00 - 235,300.00 * Based in New York, New Jersey, Washington State, or California (outside of the San Francisco Bay area):199,280.00 - 249,100.00 * Based in the San Francisco Bay area, California: 221,360.00 - 276,700.00 * This role may be eligible to participate in Twilio’s equity plan and corporate bonus plan. All roles are generally eligible for the following benefits: health care insurance, 401(k) retirement account, paid sick time, paid personal time off, paid parental leave. The successful candidate’s starting salary will be determined based on permissible, non-discriminatory factors such as skills, experience, and geographic location.  Application deadline information Applications for this role are intended to be accepted until July 25th but may change based on business needs.  Twilio thinks big. Do you? We like to solve problems, take initiative, pitch in when needed, and are always up for trying new things. That's why we seek out colleagues who embody our values — something we call Twilio Magic. Additionally, we empower employees to build positive change in their communities by supporting their volunteering and donation efforts. So, if you're ready to unleash your full potential, do your best work, and be the best version of yourself, apply now! If this role isn't what you're looking for, please consider other open positions. Twilio is proud to be an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, consistent with applicable federal, state and local law. Qualified applicants with arrest or conviction records will be considered for employment in accordance with the Los Angeles County Fair Chance Ordinance for Employers and the California Fair Chance Act. Additionally, Twilio participates in the E-Verify program in certain locations, as required by law.