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

Note: The job is a remote job and is open to candidates in USA. Smartsheet has been empowering teams for over 20 years with innovative work management solutions. The Senior Software Engineer II will be responsible for owning agent quality, diagnosing failures, and driving improvements in AI-powered work management tools.

Responsibilities

• Own agent quality end-to-end: diagnosis, improvement, and validation across SmartAssist's orchestrator and subagents
• Identify failure modes across quality dimensions factual accuracy, completeness, tone, actionability, and latency and prioritize what to fix
• Drive quality improvements through prompt engineering, context engineering, and RAG retrieval tuning
• Extend and mature our evaluation framework: scorers, golden datasets, regression gates, and online evaluation for production traffic
• Close the feedback loop ensure that every change has a measurable, attributable quality signal
• Collaborate with our Agent Architecture lead to distinguish quality problems that require prompt/context solutions from those that require structural fixes
• Establish repeatable methodology that scales beyond any single agent or subagent

Skills

• 8+ years of software engineering experience, with at least 2 years working directly with LLMs in production
• Deep, hands-on experience with prompt engineering and context engineering, you understand how model behavior changes with framing, structure, and input design
• Strong working knowledge of RAG architectures: chunking strategies, embedding models, retrieval evaluation, and failure diagnosis
• Experience building or extending LLM evaluation frameworks, you have designed scorers, worked with golden datasets, and thought carefully about what good looks like
• Fluency in agent system design, you don't need to own the architecture, but you can engage as a peer on architectural tradeoffs that affect quality
• Strong 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 room
• Strong cross-functional judgment, you know when to escalate, when to resolve independently, and how to build credibility across engineering, product, and AI platform teams
• A 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 consensus
• Legally eligible to work in the U.S. on an ongoing basis
• BS or MS in Computer Science, a related field, or equivalent industry experience
• Experience with MLflow or similar experiment tracking platforms
• Familiarity with CI-integrated evaluation pipelines
• Experience with multi-agent orchestration frameworks
• Prior work in an Applied AI or LLMOps function within a product company

Benefits

• Employer subsidized medical/vision and dental coverage for full-time employees
• 401k 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 productivity
• Flexible Time Away Program, plus Sick Time Off
• US employees are automatically covered under Smartsheet-sponsored life insurance, short-term, and long-term disability plans
• US employees receive 12 paid holidays per year
• Up to 24 weeks of Parental Leave
• Personal paid Volunteer Day to support our community
• Opportunities for professional growth and development including access to Udemy online courses
• Company Funded Perks, including a counseling membership, local retail discounts, and your own personal Smartsheet account
• Teleworking options from any registered location in the U.S. (role specific)
• This role will be eligible for a market competitive incentive opportunity

Company Overview