Smartsheet

Sr. Software Engineer II - AI Engineering (Remote Eligible)

Smartsheet$175K — $245K *
US-AnywhereRemote in United States
Information Technology
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 8+ years of software engineering experience, including 2 years with LLMs in production
  • Deep hands-on experience with prompt and context engineering
  • Strong knowledge of RAG architectures and failure diagnosis techniques
  • Experience building LLM evaluation frameworks and defining quality metrics
  • Fluency in agent system design methodologies
  • Strong Python skills in data-heavy environments
  • Excellent communication skills for conveying complex findings
  • Strong cross-functional judgment for navigating technical collaborations
  • Bias for clarity in ambiguous situations
  • Legally eligible to work in the U.S. with a BS or MS in Computer Science or equivalent experience

Responsibilities

  • Design and build production-grade LLM-powered agents and workflows
  • Develop and optimize prompts and LLM evaluation frameworks
  • Implement and manage end-to-end AI systems on cloud infrastructure
  • Collaborate with Engineering, Product, and cross-functional teams
  • Mentor and guide engineers on applied ML best practices
  • Establish AI development best practices and standards
  • Stay updated with advancements in AI and emerging tools
  • Contribute to both legacy and new applications

Benefits

  • Employer-subsidized medical, vision, and dental coverage
  • 401k match for retirement savings
  • Monthly productivity stipend
  • Flexible Time Away Program and Sick Time Off
  • Life insurance and disability coverage
  • 12 paid holidays per year
  • Up to 24 weeks of parental leave
  • A Personal Volunteer Day for community support
  • Opportunities for professional growth via Udemy courses
  • Company-funded perks including counseling membership and retail discounts
  • Teleworking options available for eligible roles
Full Job Description
You Will:
  • Design and build production-grade LLM-powered agents and workflows within Smartsheet, including architecture decisions on system design, data pipelines, and deployment strategies
  • Develop and optimize prompts, RAG pipelines, and agent reasoning patterns; build evaluation frameworks to measure accuracy, hallucination rates, and performance across model versions
  • Implement and manage end-to-end AI systems on cloud infrastructure (AWS, GCP, or Azure), including monitoring, optimization, and incident response
  • Collaborate with Engineering, Product, and cross-functional teams to translate business requirements into technical AI solutions that drive real impact
  • Mentor and guide other engineers on applied ML best practices, modern AI development patterns, and production considerations
  • Establish best practices and standards for AI development, model governance, and responsible AI within the organization
  • Stay current with the rapidly evolving AI/LLM landscape and evaluate emerging tools, frameworks, and techniques for Smartsheet's needs
  • Contribute to a full stack application- both legacy and greenfield
You Have:
  • 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:
  • 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


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

About Smartsheet

Smartsheet is a software as a service (SaaS) company that provides businesses with collaboration and work management tools. The company's platform allows teams to manage and automate workflows, projects, and processes. Smartsheet's software is used by over 90% of the Fortune 100 companies and has over 15 million registered users. The company was founded in 2005 and is headquartered in Bellevue, Washington.
Learn more about Smartsheet
Size
2,539 employees
Market Cap
$4.9 billion
Industry
Net Income
-$114.4 million
Founded
2005
5 Year Trend
+52.4%
Revenue
$354.1 million
NASDAQ

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