Senior Software Engineer II - Applied AI and Evaluations (Remote Eligible) at Smartsheet

For over 20 years, Smartsheet has helped people and teams achieve–well, anything. From seamless work management to smart, scalable solutions, we’ve always worked with flow. We’re building tools that empower teams to automate the manual, uncover insights, and scale smarter. But more than that, we’re creating space– space to think big, take action, and unlock the kind of work that truly matters. Because when challenge meets purpose, and passion turns into progress, that’s magic at work, and it’s what we show up for everyday. 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 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 You Have: Required • 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 Strong Plus • 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 What Success Looks Like: In your first 6 months, you will have: • Delivered measurable, validated quality improvement on at least one SmartAssist agent across our defined quality dimensions • Expanded evaluation coverage to close the most significant blind spots in our current framework • Established a repeatable quality improvement methodology the broader team can apply Why This Role: • You will have real ownership, not a supporting role on someone else's roadmap • SmartAssist is shipping to real users; this work has immediate, visible impact • You will be part of a fast-moving team that deeply values engineering rigor and actively seeks diverse perspectives Current US Perks & 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) 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. US Base Salary Pay Range$175,000—$245,000 USD 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, and India. 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