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SmartsheetSM

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

The foundation for managing projects, programs, and processes that scale.

Smartsheet

Employee count: 1001-5000

Salary: 175k-245k USD

United States only

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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.

About the job

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Posted on

Job type

Full Time

Experience level

Salary

Salary: 175k-245k USD

Education

Bachelor degree
Postgraduate degree

Experience

8 years minimum

Experience accepted in place of education

Location requirements

Hiring timezones

United States +/- 0 hours

About Smartsheet

Learn more about Smartsheet and their company culture.

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The foundation for managing projects, programs, and processes that scale.

Since our founding in 2005, Smartsheet has enabled individuals and teams to become high achievers. We do this by creating innovative work management solutions, mobilizing a passionate and diverse global team, and making a positive impact in communities where we live and work.

Today, Smartsheet is present in nonprofit organizations, small businesses, and more than 80% of Fortune 500 companies around the globe.

Our game-changing platform is redefining the possibilities of work management and empowering people to do amazing things.

Value-driven culture: Our award-winning culture stems from a core belief that great work experiences have the power to inspire, transform, and move the world forward.

Meaningful impact: We're working with our employees and communities to unlock the power to achieve for everyone and leave a lasting impact on the world.

Investing in employees: We help employees reach their full potential by nurturing a supportive, respectful culture that cares about well-being — both in and outside of the workplace.

Our values drive us

Our values are the beliefs that guide us, and define what we believe is a better way to work:

  • Seizing opportunity: We’re comfortable getting uncomfortable, because we know that if we’re not continuously evolving and improving, we’re falling behind.

  • Winning with integrity: We love to win, but not at all costs. We always strive to act with honesty and transparency, and to do the right thing, even when it’s hard.

  • Prioritizing “We” before “Me”: We work together as one team in service of our mission, and celebrate the big and small successes of each other and our customers along the way.

  • Pursuing progress: We believe deeply that better, fairer, and further is always possible. We work in progress and empower others to do the same—for individuals, for business, and for society.

Employee benefits

Learn about the employee benefits and perks provided at Smartsheet.

View benefits

Paid parental leave

Paid family leave for all parents to support you and your family.

Equity benefits

Eligible employees may participate in our employee stock purchase program (ESPP).

Life insurance

US employees are automatically covered under Smartsheet-sponsored life insurance.

Volunteer opportunities

If you want to volunteer your time to make the world a better place, we’ll pay for that.

View Smartsheet's employee benefits
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Smartsheet

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