[Remote] Senior Software Engineer II - Applied AI (Remote Eligible)

Note: The job is a remote job and is open to candidates in USA. Smartsheet is a company that empowers teams to manage work seamlessly through innovative solutions. They are seeking a Senior Software Engineer II to lead the design and ownership of the core infrastructure for AI experiences, focusing on building a robust environment that supports scalable AI features. The role involves architecting APIs, ensuring AI trust and safety, and driving technical strategy for AI infrastructure.ResponsibilitiesBuild the AI Platform Foundation: Lead the design and ownership of the core infrastructure that serves as the backbone for all Smartsheet AI experiences. Focus on building a robust, multi-tenant environment that reduces friction for internal teams, allowing them to deploy reliable and scalable AI features with easeStandardize the AI Developer Path: Architect high-level abstractions and "Golden Path" APIs that democratize AI development across Smartsheet. By insulating product teams from infrastructure complexity, you will enable them to ship intelligent features with high velocity while guaranteeing safety and consistency at scaleEngineer AI Trust & Safety Systems: Establish the mission-critical monitoring and quality assurance layers that protect Smartsheet customers. By creating rigorous evaluation pipelines, you will ensure every AI-driven feature meets the high bar for safety, data privacy, and deterministic performance expected by our enterprise partnersDrive technical strategy: Partner with principal engineers to define the technical roadmap for Smartsheet’s AI infrastructure, making architectural decisions that will shape how we build with AI for years to comeSkills8+ years of software engineering experience, with at least 2 years working directly with LLMs in productionDeep, hands-on experience with prompt engineering and context engineering, you understand how model behavior changes with framing, structure, and input designStrong working knowledge of RAG architectures: chunking strategies, embedding models, retrieval evaluation, and failure diagnosisExperience building or extending LLM evaluation frameworks, you have designed scorers, worked with golden datasets, and thought carefully about what good looks likeStrong Python skills; comfortable working in data-heavy environments (Databricks, Delta tables, or equivalent)Ability to communicate complex quality findings (written and verbal) to both technical and non-technical stakeholders, you can explain what's broke, why it matters, and what needs to happen next without losing the roomStrong cross-functional judgment, you know when to escalate, when to resolve independently, and how to build credibility across engineering, product, and AI platform teamsA bias for clarity in ambiguous situations, when failure modes are murky and trade-offs are real, you bring structure and a clear point of view rather than waiting for consensusPrior work in an Applied AI or LLMOps platform within a product companyExperience with the following: Kubernetes (EKS/GKE): The industry standard for AI. Skills include managing GPU scheduling, auto-scaling based on token throughput, and using tools like Karpenter for cost-efficient node provisioningInfrastructure as Code (IaC): Using Terraform, Pulumi, or AWS CDK to provision Vector Databases, SQS queues, and S3 bucketsVector Databases: Proficiency in managing and optimizing Pinecone, Milvus, Weaviate, or Databricks Vector SearchAI Gateways: Building or configuring proxies (like LiteLLM or Kong AI Gateway) to handle rate-limiting, PII masking, and cost-trackingLLM Observability: Setting up tracing tools like Langfuse, LangSmith, or MLflow to monitor 'Time to First Token' (TTFT) and trace hallucination issuesModel-Based Evals: Implementing automated scoring systems (like RAGAS or DeepEval) that use an 'LLM-as-a-Judge' to grade production outputsBenefitsEmployer subsidized medical/vision and dental coverage for full-time employees401k Match to help you save for your future (50% of your contribution up to the first 6% of your eligible pay)Monthly stipend to support your work and productivityFlexible Time Away Program, plus Sick Time OffUS employees are automatically covered under Smartsheet-sponsored life insurance, short-term, and long-term disability plansUS employees receive 12 paid holidays per yearUp to 24 weeks of Parental LeavePersonal paid Volunteer Day to support our communityOpportunities for professional growth and development including access to Udemy online coursesCompany Funded Perks, including a counseling membership, local retail discounts, and your own personal Smartsheet accountTeleworking options from any registered location in the U.S. (role specific)Company OverviewSmartsheet is a cloud-based work management platform that empowers collaboration, drives better decision-making, and accelerates innovation. It was founded in 2005, and is headquartered in Bellevue, Washington, USA, with a workforce of 1001-5000 employees. Its website is https://www.smartsheet.com.Company H1B SponsorshipSmartsheet has a track record of offering H1B sponsorships, with 10 in 2026, 54 in 2025, 58 in 2024, 46 in 2023, 57 in 2022, 32 in 2021, 41 in 2020. Please note that this does not guarantee sponsorship for this specific role.