Senior Software Engineer II – Applied AI

Job Description

Join Smartsheet as a Senior Software Engineer and drive the future of AI. You'll lead the design of the core AI platform, creating a scalable environment for AI feature deployment. Standardize AI development with high-level APIs, enabling rapid and safe feature releases. Engineer AI trust and safety systems to protect customers with rigorous evaluation pipelines. Partner with principal engineers to define the technical roadmap for Smartsheet's AI infrastructure, shaping how we build with AI for years to come.

Qualifications

1. 8+ years of software engineering experience, including 2+ years with LLMs in production. 2. Strong experience with prompt and context engineering, understanding how model behavior changes. 3. Solid understanding of RAG architectures: chunking, embeddings, retrieval evaluation, and failure diagnosis. 4. Experience building or extending LLM evaluation frameworks with scorers and golden datasets. 5. Strong Python skills, comfortable in data-heavy environments (Databricks, Delta tables). 6. Ability to communicate complex findings to technical and non-technical stakeholders. 7. Strong cross-functional judgment, knowing when to escalate and how to build credibility. 8. A bias for clarity in ambiguous situations, bringing structure to murky failure modes. 9. Plus: Prior work in an Applied AI or LLMOps platform within a product company. 10. Experience with Kubernetes (EKS/GKE), Terraform, Pulumi, or AWS CDK, Vector Databases (Pinecone, Milvus, Weaviate), AI Gateways (LiteLLM, Kong AI Gateway), LLM Observability (Langfuse, LangSmith), and Model-Based Evals (RAGAS, DeepEval).

Benefits

- Employer-subsidized medical/vision and dental coverage. - 401k Match (50% up to the first 6% of eligible pay). - Monthly stipend for work and productivity support. - Flexible Time Away Program and Sick Time Off. - Smartsheet-sponsored life insurance, short-term, and long-term disability plans. - 12 paid holidays per year. - Up to 24 weeks of Parental Leave. - Personal paid Volunteer Day. - Professional growth opportunities with access to Udemy online courses. - Company-funded perks: counseling membership, local retail discounts, personal Smartsheet account. - Teleworking options from any registered location in the U.S.