Sr. Forward Deployed AI Engineer (Remote Eligible in the UK)

For over 20 years, Smartsheet has empowered teams to manage work seamlessly and scale solutions smarter. Now, in our most ambitious chapter yet, we are uniting human teams with AI agents. By orchestrating the work agents do best, automating manual tasks and uncovering insights at scale, we create the space for people to focus on what truly matters: judgment, creativity, and big thinking. That is magic at work, and it’s what we show up for every day. We are seeking a Senior DevOps Engineer to join the team that owns and operates Smartsheet's edge proxy platform and internal engineering tooling. The edge proxy is a custom-built, high-performance reverse proxy that serves as the entry point for all traffic across Smartsheet's commercial and FedRAMP-authorised US Government environments. The team owns the full lifecycle of this platform: from maintaining the proxy binary and its configuration tooling, to provisioning and operating the multi-region AWS EKS infrastructure it runs on, to managing the observability and on-call story for every service that routes through it. Beyond the edge layer, the team also drives the evaluation and adoption of internal developer tooling — from developer portals to productivity platforms — that improves the engineering experience across the company. You will work remotely from Bulgaria and will be reporting to an engineering leader. You Will: * Own and evolve the edge proxy platform: Maintain, upgrade, and extend a high-performance reverse proxy — including maintaining the proxy binary and its configuration tooling, writing Go and Python automation, managing the full container image lifecycle on hardened Linux base images, and working across the broader edge layer, including CDN, WAF, and traffic management capabilities. * Build and maintain cloud infrastructure as code: Design and implement Terraform/Terragrunt modules and live environment configurations managing EKS clusters, load balancers, IAM roles, VPC networking, ECR registries, and supporting AWS services across multiple regions including GovCloud. * Operate Kubernetes clusters at scale: Manage multi-region, multi-cluster EKS deployments via FluxCD GitOps workflows and Helm charts, including node AMI rotation, add-on lifecycle management, and horizontal pod autoscaling. * Build and own CI/CD pipelines: Design, maintain, and improve shared GitLab CI/CD pipeline templates used across all team repositories; build and operate alternative pipeline workflows for isolated government cloud environments. * Automate operational toil: Build and maintain tooling for tasks such as container image patching, EKS AMI rotation, air-gapped ECR image sync to GovCloud, and automated MR creation for monthly version-bump patching cycles. * Manage observability and on-call: Provision and maintain Datadog SLOs, monitors, and dashboards via Terraform; participate in the team's on-call rotation responding to edge proxy incidents across production and GovCloud environments. * Support FedRAMP/GovCloud operations: Operate the GovCloud environment with its unique constraints — air-gapped image distribution, infrastructure automation in isolated networks, and alert management with compliance-aware data handling. * Evaluate and adopt internal developer tooling: Research, prototype, and drive the adoption of internal tools that improve engineering productivity across the company — including developer portals, platform self-service capabilities, and other tooling that raises the bar for the developer experience at Smartsheet. * Mentor and collaborate: Share knowledge across the team through code reviews, architecture discussions, and runbook authorship; foster a culture of engineering excellence and operational rigour. * Strategically apply AI tools: Strategically apply and champion AI tools within your team's domain to improve project execution, infrastructure design, quality, and debugging, leading adoption of AI best practices. You Have: * 8+ years of experience in DevOps, platform engineering, or site reliability engineering. * A BS or MS in Computer Science, Engineering, or a related field, or equivalent industry experience. * Deep proficiency with Terraform and Terragrunt for managing production cloud infrastructure at scale across multiple environments and regions. * Strong Kubernetes expertise, including EKS cluster operations and Helm chart authoring. * Hands-on experience with AWS networking and container workload services: EKS, ALB/NLB, VPC, IAM, ECR, Route53, CloudWatch, and EventBridge. * Proficiency in at least one general-purpose programming language — Go or Python preferred — for building operational tooling and automation. * Solid understanding of reverse proxies, API gateways, or load balancers (NGINX, HAProxy, or equivalent). * Experience designing and maintaining CI/CD pipelines (GitLab CI preferred), including shared template libraries across multiple repositories. * Experience with container image security practices: hardened base images, vulnerability scanning, and image promotion workflows. * Strong operational instincts: comfort with on-call responsibilities, incident response, runbook authorship, and postmortems in production environments. * 1 year of professional experience leveraging AI-based workflows to author, maintain, review, and deploy infrastructure or code. * Fluency in English is required. * Legally eligible to work in Bulgaria on an ongoing basis. Nice to Have: * Experience with enterprise CDN platforms, including WAF configuration, origin routing, and cache policy management. * Familiarity with FedRAMP or AWS GovCloud operational constraints. * Experience with advanced reverse proxy or API gateway configuration, including programmatic config generation, dynamic routing, and service mesh components. * Experience managing Datadog resources via Terraform: SLO definitions, monitors, and dashboards. * Familiarity with rate-limiting services, control plane components, or custom traffic filter development. Smartsheet provides a competitive base salary range for roles that may be hired in different geographic areas we are licensed to operate our business from. Actual compensation is determined by several factors including, but not limited to, level of professional, educational experience, skills, and specific candidate location. In addition, this role will be eligible for a market competitive incentive opportunity. Bulgaria Base Salary Pay Range €70,250 - €83,000 EUR   Get to Know Us: At Smartsheet, your ideas are heard, your potential is supported, and your contributions have real impact. You’ll have the freedom to explore, push boundaries, and grow beyond your role. We welcome diverse perspectives and nontraditional paths—because we know that impact comes from individuals who care deeply and challenge thoughtfully. When you’re doing work that stretches you, excites you, and connects you to something bigger, that’s magic at work. Let’s build what’s next, together. Equal Opportunity Employer: Smartsheet is an Equal Opportunity (EEO) employer committed to fostering an inclusive environment with the best employees. It is our policy to provide equal employment opportunities to all qualified applicants in accordance with applicable laws in the US, UK, Australia, Germany, Costa Rica, Japan, Bulgaria, India, and Singapore. All qualified applicants will receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information.  If there are preparations we can make to help ensure you have a comfortable and positive interview experience, please let us know.   #LI-Remote

For over 20 years, Smartsheet has empowered teams to manage work seamlessly and scale solutions smarter. Now, in our most ambitious chapter yet, we are uniting human teams with AI agents. By orchestrating the work agents do best, automating manual tasks and uncovering insights at scale, we create the space for people to focus on what truly matters: judgment, creativity, and big thinking. That is magic at work, and it’s what we show up for every day. We are seeking a passionate and experienced Sr. Software Engineer I to join our Security Application Development team. In this role, the successful candidate will be instrumental in designing, building, and maintaining robust security features for our SaaS product that will delight our customer CIOs. This position involves working on challenging problems at the intersection of application development and security, directly contributing to the resilience and trustworthiness of our platform. This is an exciting opportunity to leverage software development expertise to create secure-by-design solutions that protect our customers and their data 24/7. You will work remotely from Bulgaria. You Will: * Design, build, and implement security features and functionalities directly into our SaaS product using modern programming languages (e.g., Java, Kotlin, Go, TypeScript, Python) and associated frameworks, applying deep technical knowledge and sustained concentration to deliver secure-by-design solutions. * Develop scalable back-end services and APIs with a security-first mindset, ensuring high availability and performance in our multi-cloud environment (primarily AWS), requiring careful planning and prioritisation across concurrent workstreams. * a with product and engineering teams to embed security best practices throughout the entire software development lifecycle, from design to deployment, communicating clearly and engaging constructively with stakeholders across disciplines. * Engineer and automate security controls, threat detection mechanisms, and vulnerability remediation processes within the application, exercising independent analytical judgement to identify and resolve complex problems. * Participate actively in code reviews and architectural discussions, advocating for secure coding practices and robust security designs, and contributing to well-documented technical decisions. * Tackle complex security challenges related to data protection, access control, authentication, authorisation, and secure communication within a distributed system, maintaining focus and rigour under pressure. * Create and maintain API integrations between internal and external systems, implementing and testing API solutions to ensure they meet functionality, performance, and security standards, and monitoring integration health on an ongoing basis. * Serve as a subject matter expert in application security, mentoring junior engineers and fostering a culture of security ownership across development teams, actively supporting the growth and capability of peers. * Strategically apply and champion AI tools within the team's domain to improve project execution, system design, quality, and debugging, leading adoption of AI best practices and driving measurable productivity gains. * Assist with security incident remediation in support of the globally operated 24/7 Security Operations Centre, contributing during daytime working hours and demonstrating resilience and composure when managing time-sensitive situations. * Handle sensitive security-related data, documentation, and incident records with appropriate confidentiality and rigour, maintaining accurate reporting in line with internal standards. * Perform all work using standard computer and keyboard use in a remote environment, with standard sedentary work involving extended screen use. You Have:  * 5+ years of progressive software development experience, with at least 3 years focused on building security features or secure applications, demonstrating sustained growth in technical depth and professional knowledge. * A Bachelor's or Master's degree in Computer Science, Engineering, or a related field, or equivalent industry experience providing the same level of knowledge and competency. * Expert-level proficiency in at least one major programming language such as Java, Kotlin, Go, or Python, with a proven history of building scalable and secure applications. * Deep experience with cloud technologies (AWS, Azure, etc.), particularly in securing cloud-native applications, and familiarity with the tools, platforms, and infrastructure involved in multi-cloud environments. * Experience developing, documenting, and supporting secure REST APIs, with attention to detail in both implementation and written technical documentation. * Strong understanding of common security vulnerabilities (e.g., OWASP Top 10) and mitigation techniques, with the ability to apply this knowledge independently and under pressure. * Experience with containerisation and orchestration technologies (Kubernetes) in a secure development context. * Proficiency with modern security tools and practices, including static application security testing (SAST), dynamic application security testing (DAST), and software composition analysis (SCA). * Proven ability to troubleshoot complex security-related problems in high-pressure production environments, demonstrating critical thinking and sound independent judgement. * Excellent verbal and written communication skills in English, and a collaborative approach to working with cross-functional teams and stakeholders at all levels. * 1+ year of professional experience leveraging AI-based workflows to author, maintain, review, deploy, and maintain code. * 1+ year of experience building AI features that incorporate generative AI or agentic workflows to solve customer problems with measurable business impact. * Comfort working with ambiguity and shifting priorities in a fast-paced environment, with the psychosocial resilience to manage sustained cognitive effort and occasional incident-driven pressure. * No direct financial responsibility is associated with this role, though awareness of cost implications in architectural and tooling decisions is expected. * Ability to work independently in a remote setting within a psychologically safe and inclusive team environment, with standard flexible working hours aligned to the Bulgaria time zone and no travel requirements expected for this role. * Legal eligibility to work in Bulgaria on an ongoing basis. * Fluency in English is required. Nice to Have: * Advanced industry certifications such as CSSLP, OSCP, or cloud-specific security certifications. Smartsheet provides a competitive base salary range for roles that may be hired in different geographic areas we are licensed to operate our business from. Actual compensation is determined by several factors including, but not limited to, level of professional, educational experience, skills, and specific candidate location. In addition, this role will be eligible for a market competitive incentive opportunity. Bulgaria Base Salary Pay Range €58,250 - €69,750 EUR   Get to Know Us: At Smartsheet, your ideas are heard, your potential is supported, and your contributions have real impact. You’ll have the freedom to explore, push boundaries, and grow beyond your role. We welcome diverse perspectives and nontraditional paths—because we know that impact comes from individuals who care deeply and challenge thoughtfully. When you’re doing work that stretches you, excites you, and connects you to something bigger, that’s magic at work. Let’s build what’s next, together. Equal Opportunity Employer: Smartsheet is an Equal Opportunity (EEO) employer committed to fostering an inclusive environment with the best employees. It is our policy to provide equal employment opportunities to all qualified applicants in accordance with applicable laws in the US, UK, Australia, Germany, Costa Rica, Japan, Bulgaria, India, and Singapore. All qualified applicants will receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information.  If there are preparations we can make to help ensure you have a comfortable and positive interview experience, please let us know.   #LI-Remote