Staff Engineer, Site Reliability

LearnUpon

Work Mode: Hybrid 1+ day per week in our Dublin office Department: Engineering   ABOUT THE COMPANY  LearnUpon partners with over 1,600 organisations globally to unlock the potential of employees, customers & members through learning that’s easy, scalable and focused on results. Read more about life at LearnUpon here.    ABOUT THE TEAM Our Engineering team builds and delivers our best-in-class, world-scale Learning Management System (LMS). We focus on architectural excellence, reliability, and technical innovation across multiple teams and services. Operating with high ownership and deep technical expertise, we champion engineering best practices, seamless automation, and a strong culture of collaborative mentorship to support LearnUpon's global product growth.   ABOUT THE OPPORTUNITY As a Staff Engineer, DevOps, you'll be a key technical leader and role model within LearnUpon. You'll shape the DevOps architecture of our best-in-class LMS, influence our technical strategy, and elevate the skills of our entire engineering organization. Your impact will extend beyond our product, contributing to our mission of building robust, lovable learning products that help customers achieve results. In addition, you’ll be responsible for: * Architecture & Strategy: Drive technical innovation, shape our long-term technical roadmap, and establish scalable DevOps architecture across multiple platform services * Automation & CI/CD: Establish and scale robust CI/CD pipelines and infrastructure automation, driving best practices across the engineering organization * Operational Excellence: Champion absolute standards for code quality, system design, scalability, and cloud production reliability * Mentorship & Leadership: Provide strategic technical guidance, acting as a prominent role model to uplevel the skills of our entire engineering and senior technical talent pool * Stakeholder Alignment: Collaborate closely with Product Engineering and cross-functional leadership to align infrastructure capabilities with business goals   SKILLS & EXPERIENCE  Must-Haves                                                                          * Proven expertise in cloud infrastructure, particularly within AWS environments, with an advanced understanding of production scalability, security, and reliability * Strong production experience working with Kubernetes and Helm charts as the foundational layer for container platform orchestration * Deep proficiency in Infrastructure as Code (IaC) frameworks like Terraform or Ansible, focusing on modular and reusable architecture patterns * Extensive background designing CI/CD pipelines (GitLab preferred) and engineering automated internal tooling using Bash, Python, or Go * Demonstrated success leading large-scale technical initiatives that span across multiple engineering squads and services * Track record of mentoring, coaching, and elevating senior-level technical talent * Experience using AI tools to streamline tasks and improve efficiencies   Nice-to-Haves * Familiarity with GitOps deployment workflows using tools such as ArgoCD or FluxCD * Prior experience optimizing massive multi-tenant platform infrastructure within a high-growth B2B SaaS architecture *If you don’t tick every box but believe this role is a mutually good fit, please don’t hesitate to apply. We’d love to hear from you.   WHY CHOOSE LEARNUPON? From comprehensive rewards and generous time off to meaningful investment in your growth and development, LearnUpon gives you the support, trust, and opportunity to do the most impactful work of your career. Learn more here.    HIRING PROCESS * Qualified applicants may be invited to an initial screening call with a member of our TA Team. * Successful candidates will be invited to a series of practical interviews. * Finally, candidates will have an interview with our CTO. * Successful candidates will be contacted with an offer to join our team.   Note: At LearnUpon, we utilise AI to enhance the speed and quality of our screening and assessment practices, but our hiring decisions are always human.    LearnUpon is an Equal Opportunities Employer.  We do not discriminate on the basis of gender, marital status, family status, age disability, sexual orientation, race, religion, membership of the Traveller community, or any other legally protected status.   Check out our Careers site and Instagram to learn more about working at LearnUpon.   By submitting your application, you agree to LearnUpon's Privacy Policy.

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. We’re not your traditional tech company and we don’t aim to be. Going against the grain is in our DNA. Building a revolutionary product begins with revolutionary thinking. That’s why we value diversity of background and lived experience. Together, we empower restaurants of all sizes to build great teams, increase revenue, improve operations, and delight their guests. We pair our deep understanding of the restaurant industry with powerful cloud based software and restaurant-grade hardware to deliver an intuitive all-in-one platform. Join us on our mission to empower the restaurant community to delight guests, do what they love, and thrive. Fintech at Toast operates one of the most critical portions of the Toast infrastructure: processing payments on behalf of our restaurants and ensuring that restaurants are paid in a timely manner. Payment processing is a key source of Toast’s revenue and also the lifeblood of our customers; we process millions of dollars in transactions per day.   We are seeking a Staff Software Engineer to join our Payments team to build our next generation payment processing platform by combining deep payments expertise with experience building AI agents and agentic systems. This platform offers a single, integrated service for payment acceptance across various channels and supports a configurable enterprise approach. It is designed to allow a build-once, available-to-all strategy for both existing and emerging payment methods. The successful candidate will guide and contribute to the development of services providing supporting and core functionality within and around this payment processing solution.   A day in the life (Responsibilities) * Plan, design, build, and deliver features for Toast’s payments products  * Roll - pun intended! - features out to customers, including monitoring for success * Collaborate with our PM (and UX) on the definition and design of features   * Collaborate and partner with a wide array of teams across Toast in order to spread knowledge inter- and intra-team * Participate in designing, estimating, implementing, testing, and debugging end-to-end agent solutions * Adopt and advocate for bleeding-edge spec-driven development and agentic development practices * Champion best practices for agent development, deployment, and quality life cycles * Lead and work with experienced engineers to deliver design and code review   What you'll need to thrive (Requirements) * 8+ years of experience in designing and implementing robust backend services * Experience or strong interest in using coding agents and adopting agentic development practices * Ability to step into a technical leadership role on the team, guiding/coaching/mentor more junior engineers on best practices in architecture, design, coding, testing, deployment, etc. * Proven ability to design and develop scalable and secure APIs that integrate with various internal/external systems * Applied knowledge of best practices in API lifecycle management, including versioning, documentation, and deprecation strategies, with the ability to share this amongst the team and peers * Demonstrated experience with microservices architecture and containerization technologies for enhanced scalability and maintainability Special Sauce (*Nice to Haves)   * Experience designing agentic products * Demonstrated proficiency with DynamoDB or PostgreSQL * Proficiency in Kotlin (or Java and willing to learn Kotlin) and Kotlin-specific frameworks and libraries for building efficient backend solutions * Experience with modern data architectures (event sourcing, OLAP, ETL/ELT, streaming data) * Experience designing payments APIs * Familiarity with PCI-DSS * Familiarity with AI-augmented development workflows and tools (e.g., Claude Code, GitHub Copilot, Codex, or similar)   #LI-HYBRID #BI-Hybrid 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. 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.

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. Your mission is to drive architecture, technical strategy, and implementation of AI agents for Toast's Team area which is part of the Fintech line of business. You will be one of the most senior technologists in line of business. The Team area is a mission-critical space on which our restaurants rely to manage their staff and optimize their labor. Beyond being on the forefront of agent development, your scope will also include enablement and leadership for how software is developed at Toast through adoption of bleeding edge spec driven development and other paradigms.  A day in the life (Responsibilities) * Develop and drive an architectural vision to support the ambitious goals for agents and agent development * Be an active participant and an authoritative technical voice in FinTech product strategy discussions * Partner with the Team Management Director of Engineering and Sr. Director of Product to successfully deliver Team agent products from design to production * Work closely with other Senior Principal Engineers to further the agent patterns and ecosystem across Toast as a whole * Evolve an ever more efficient way of working through agents and spread it across Toast * Work directly with the product manager for the Team Agent space, collaborating to drive vision * Be hands on and actively participate in development on the Team Agent * Mentor and develop technical leadership across Team, and Fintech What you'll need to thrive (Requirements) * 15+ years experience designing and building highly scalable, mission-critical distributed and fullstack software systems * 10+ years experience building and operating SaaS products, ideally AWS hosted * A strong desire to lean all in on agentic development practices * Passion for building autonomous agents * Demonstrated ability to drive technical architecture for a company or highly scalable line of products * A desire to work not only with technologists but also product owners and business leaders * Ability and desire to draw big lines and boxes on a whiteboard paired with the ability to dig in and understand the ebb and flow of what the code is doing under load * Ability and desire to communicate and influence at the executive level What will help you stand out (Nonessential Skills/Nice to Haves) * Experience designing agentic products * Experience building systems that leverage LLMs and other ML models * Experience with enterprise integration using Apache Camel * Experience architecting event-driven distributed systems using Apache Pulsar * Experience defining test, build and deploy strategies * Solid understanding of workforce management * Solid understanding of restaurant operations Location: Remote (within Ireland) or Hybrid (Dublin) #LI-Remote   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. 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.