[Hiring] Senior Software Engineer II - Applied AI and Evaluations @Smartsheet

Role Description

Smartsheet is building the next generation of AI-powered work management through SmartAssist, our intelligent agent platform. As we scale from early demos to production-grade agents, quality is the critical frontier and we are looking for a Agent Quality Engineer to own it.

This is not a QA role. It's a deeply technical, high-autonomy position at the intersection of LLM evaluation, prompt and context engineering, and retrieval-augmented generation. You will diagnose why our agents fail, design the systems that catch regressions, and drive measurable improvements across our orchestrator and subagent fleet.

You will work closely with our Agent Engineering and AI Platform teams, embedded in a team that has already shipped evaluation infrastructure on Databricks/MLflow and is building toward a mature Agent Development Lifecycle (ADLC).

You Will:

• 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 to 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.

Qualifications

• 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, understanding 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, including designing scorers and working with golden datasets.
• Fluency in agent system design; able to 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.
• Strong cross-functional judgment; knows when to escalate, when to resolve independently, and how to build credibility across teams.
• A bias for clarity in ambiguous situations; brings 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.

Requirements

• 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).
• Competitive base salary range for roles that may be hired in different geographic areas.