Hardened Comms Engineer (All Genders)

Sr. DevOps Engineer I (Remote Eligible in Bulgaria)

Smartsheet

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: * 5+ 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. BG 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

Sr. DevOps Engineer II (Remote Eligible in Bulgaria)

Smartsheet

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

Applied AI Engineer

myTomorrows

About myTomorrows  myTomorrows is a global health tech company dedicated to breaking down barriers for patients seeking treatment options.    We strive to enable earlier and better treatment access by bridging the gap between those searching for possible options, and the companies who develop them. We work closely with patients, healthcare professionals, trial sites, patient advocacy groups, and BioPharma – connecting key stakeholders in the drug development ecosystem.    We’ve developed a cutting-edge AI-powered technology platform that simplifies and streamlines access to drugs in development. To support our users and clients, we have a range of industry-expert specialized teams ready to help. Our services include clinical trial patient recruitment, Expanded Access Program management and Real-World Data collection.    With a global footprint spanning 134 countries, to date we’ve supported over 17,000 patients, 3,000 physicians and 350 sites, earning the trust of 60+ BioPharma companies. In October 2025, we closed a €25M investment with Avego Healthcare Capital to fuel our global ambitions and scale the business.   Join us in shaping the future of treatment access - making tomorrow’s therapies accessible for people who need them today.  THE OPPORTUNITY: APPLIED AI ENGINEER As Applied AI Engineer at myTomorrows, you will help us become more AI-native in how we work, build, and deliver value to patients, physicians, trial sites and (bio-)pharma partners. Your primary focus is internal: the teams, workflows, and operational processes inside myTomorrows. This is not a pure research role, and it is not a “prompt engineer” role. You are an experienced software engineer who knows how to build reliable systems, and who is experienced with the possibilities created by LLMs, agents, AI-assisted coding, retrieval, workflow automation, and internal tooling. You will work as part of our AI Acceleration initiative: a small, high-leverage team focused on safely applying AI across the organization. You embed with internal teams, e.g. Operations, Regulatory, Commercial, Marketing, to find the highest-leverage points of intervention, build production-ready solutions, and leave behind systems that teams can own and operate without you. A key part of the role is not just building things yourself, but helping myTomorrows learn how to build with AI. You will help define reusable patterns, guardrails, evaluation approaches, and engineering practices so that AI-assisted work becomes reliable, secure, maintainable, and scalable. Given that most of our team is located in the Netherlands, we only consider candidates for this position who live within commuting distance of our office in Amsterdam. HOW YOU WORK Each engagement follows the model of a “Forward Deployed Engineer”: Insertion. When you start a mission, you sit with the people who do the actual work: not the people who manage them. You watch, you ask questions, and you map what's really happening: the tools, the manual steps, the tribal knowledge, the workarounds that nobody questions anymore. Your first deliverable is not code. It is a situational awareness map. Discovery. From that map, you identify the highest-leverage intervention point: not the most technically interesting problem, but the one that, if solved, would make the most visible difference to the most people in the shortest time. Delivery. You build production-capable solutions on real data with measurable success criteria defined upfront. You identify an internal champion in week one who will own the system after you leave, and you embed them in the work from the start. Handoff. You leave behind a running system, not a prototype. You leave behind an eval framework and runbook so the system doesn't rot. And you leave behind an AI substrate — connectors, pipelines, and workflow patterns — that makes the next mission faster. WHAT YOU’LL DO IN THIS ROLE * Build production-capable AI-enabled internal tools, workflow automations, agents, and integrations that solve real business problems by embedding with internal teams. * Use modern LLM capabilities such as structured outputs, tool calling, retrieval-augmented generation, agentic workflows, prompt/context engineering and creating evals. * Help teams translate ambiguous business problems into clear, testable, AI-assisted delivery plans. * Build backend services, APIs, integrations, and internal applications using modern software engineering practices. * Work closely with Product, Engineering, QA, DevOps, Data, Legal, Privacy, and Security to ensure AI-built software is safe, secure, observable, and maintainable. * Design and implement evaluation approaches for AI systems, including test sets, human review loops, quality criteria, failure mode analysis, and monitoring. * Create reusable playbooks, templates, prompts, Skills, MCPs and examples that help other teams adopt AI effectively. * Help assess whether a solution should remain a lightweight internal tool, be transferred to a business owner, be hardened by Product & Engineering, or be stopped. * Stay up to date with the rapidly evolving AI engineering landscape and translate relevant developments into practical opportunities for myTomorrows. WHAT YOU BRING TO THE TABLE * 3+ years of professional software engineering experience, ideally in a product, platform, backend, fullstack, startup, or scale-up environment. * Strong software engineering fundamentals. You have built and maintained real systems before (and before vibe-coding was thing), and you know that shipping reliable software is about more than generating code. * Experience with backend development, ideally with Python and modern API development. * Experience with relational databases such as MySQL, PostgreSQL, or Oracle. * Experience with cloud platforms such as AWS, Azure, or GCP. * Strong understanding of testing, code review, observability, security, documentation, and maintainability. * Hands-on experience with the modern essentials of AI agents, agentic engineering and AI coding tools: LLM APIs, agents, RAG, MCPs, Skills, workflow automation and AI-enabled product development. * Ability to work independently in ambiguous environments, while communicating clearly with technical and non-technical stakeholders. * Strong product sense: you care about solving the actual problem, not just using the newest tool. * A pragmatic startup mentality: you can move fast, make sensible trade-offs, and know when to prototype, when to harden, and when to stop. * Excellent English communication skills. NICE TO HAVE * Experience with FastAPI, Pydantic, SQLAlchemy, uv, ruff, pre-commit, GitHub Actions, or similar tools. * Experience with AWS-native architectures, infrastructure as code, Terraform, serverless, Kubernetes, or cloud-native platform work. * Experience with frontend development, especially Angular, React, TypeScript, or fullstack personal projects. * Experience building internal tools, developer tools, workflow automation, or operations tooling. * Experience with AI evaluation frameworks, model monitoring, prompt/version management, or human-in-the-loop review systems. * Experience with healthcare, pharma, clinical research, regulated environments, privacy-sensitive data, or compliance-heavy workflows. * Experience with tools such as Claude Code, Codex, Cursor, GitHub Copilot, LangChain/LangGraph, LlamaIndex, n8n, or similar AI/workflow platforms. WHAT SUCCESS IN THE FIRST 6 MONTHS LOOKS LIKE * You have built trust with Product, Engineering, DevOps, Data, and business stakeholders by delivering useful AI-enabled solutions without creating unmanaged technical debt. * You have delivered 2-3 high-impact AI Acceleration missions, such as an internal tool, workflow automation, agentic engineering improvement, or AI-assisted product delivery pilot. * You have shipped production-capable software with clear ownership, tests, documentation, observability, and security considerations. * You have created reusable templates, prompts, scripts, or examples that other teams can use. * You have helped teams understand where AI is genuinely useful, where it is not ready yet, and what guardrails are needed. * You have contributed to a culture where AI-assisted engineering is judged by objective production outcomes: correctness, security, maintainability, observability, and business value. CURRENT TECH STACK We are fully cloud-native, leveraging AWS and adopting a lean, API-first product development approach driven by modern cloud technologies and thoughtful design practices. Our current Backend Engineer posting describes a stack including Python, FastAPI, Pydantic, SQLAlchemy, MySQL/PostgreSQL, Angular, GitHub Actions, Renovate, ruff, uv, pre-commit, Docker, Docker Compose, Kubernetes, Terraform, DynamoDB, and Neo4j. As Applied AI Engineer focused on internal use cases, you will often work in lighter-weight stacks like scripts, Skills, MCPs, APIs, workflow tools, internal dashboards rather than full product infrastructure. Familiarity with the product stack is useful context, but your day-to-day tooling will be shaped by the mission. WHAT WE OFFER * Impactful work that helps patients gain access to potentially lifesaving treatments. * A unique opportunity to help define how a HealthTech scale-up becomes AI-native. * International work environment, scale-up energy, and a flat organizational structure that encourages creativity and accountability. * Competitive salary, annual performance bonus, and an Employee Stock Option Plan. * Great career development opportunities in a fast-growing company. * Learning and development budget alongside internal knowledge-sharing sessions. * Attractive pension plan, full premium covered by myTomorrows. * Hybrid working model. * Policies to support working parents. * Healthy lunch at the thriving Amsterdam office. * Unlimited access to professional guidance by certified psychologists via OpenUp. * Monthly events hosted by our vibrant Culture Club as well as an annual myTomorrowland company-wide celebration. Equal opportunities myTomorrows is an Equal Opportunity Employer and, beyond upholding discrimination-free practices, we are committed to cultivating a workplace where difference and diversity are protected and celebrated. The best work comes from our best selves, and we go to great lengths in supporting our team members to be just that.