Senior/Principal Engineer (m/f/x) for Evaluations Generative AI

Posted 5 Days Ago
Hiring Remotely in Boston, MA, USA
Remote or Hybrid
74K-112K Annually
Senior level
Artificial Intelligence • Big Data • Cloud • Information Technology • Software • Big Data Analytics • Automation
Dynatrace delivers answers and intelligent automation from data.
The Role
Design and build evaluation and simulation systems for generative AI agents using Dynatrace observability data. Create large-scale simulation pipelines, define metrics/datasets/judging strategies, build developer CLIs, generate adversarial scenarios, and measure agent tool-use and failure modes. Prototype, run feedback cycles, set technical strategy, and mentor engineers.
Summary Generated by Built In
Your role at Dynatrace

Most AI developer tools operate without any knowledge of how software actually behaves in production. Dynatrace is in a unique position to change that.

We're looking for a Senior or Principal Generative AI Engineer to design and build the evaluation and simulation capabilities at the core of our product. You'll work across the stack, from CLI tooling that engineers run locally, to large-scale simulation pipelines, to LLM-as-a-judge evaluation frameworks running against real Dynatrace AI Observability data.

This role sits inside Dynatrace's Engineering organization and works closely with product, design, and the platform teams that power Dynatrace's AI-observability stack.

Your responsibilities:

  • Conduct research in the field of Generative AI
  • Design and build systems that let users replay and stress-test AI Agents at scale. Detect regressions across model versions, prompt changes, and data drift. Define the metrics, datasets, and judging strategies that make results trustworthy.
  • Build infrastructure to simulate multi-turn, tool-using agents in realistic environments. Generate adversarial scenarios, measure task completion, tool-use correctness, and failure modes. Help teams ship agents with confidence.
  • Own developer-facing CLIs that run evaluations on top of Dynatrace AI Observability data, from trace ingestion to judge configuration to reporting. Make it the tool AI engineers reach for first when debugging a production behavior.
  • Prototype quickly, run user feedback cycles, and ship to production
  • Define technical strategy for the team's AI systems, set architectural direction, and mentor other engineers
  • Collaborate with product and design to identify which developer problems are most worth solving
What will help you succeed
  • 5+ years (Senior) or 10+ years (Principal) of professional software engineering experience
  • Demonstrated experience shipping production systems that use LLMs, including prompting, tool calling, evaluation, and iteration
  • Strong foundation in at least one of: developer tooling (IDEs, compilers, static analysis, code intelligence), AI/ML engineering, or large-scale distributed systems
  • Hands-on experience with agentic patterns: planning, tool use, retrieval, memory management
  • Ability to evaluate and critique AI-generated output. You understand when a model is wrong, not just that it is.
  • Clear communication with cross-functional partners across product and engineering
  • Background in observability, APM, or infrastructure monitoring
  • Familiarity with engineering platforms at scale: CI/CD systems, developer portals, internal tooling
  • Hands-on experience with LLMs: prompt engineering, evaluation frameworks (e.g. LLM-as-a-judge, golden datasets, pairwise comparisons), or agent frameworks.
Why you will love being a Dynatracer
  • Dynatrace is a leader in unified observability and security.
  • We provide a culture of excellence with competitive compensation packages designed to recognize and reward performance.
  • Our employees work with the largest cloud providers, including AWS, Microsoft, and Google Cloud, and other leading partners worldwide to create strategic alliances.
  • You'll get to work at the forefront of innovation with Dynatrace Intelligence—the industry's first agentic operations system. Bringing together deterministic and agentic AI, it helps teams understand what's happening, why it matters, and what to do next— automatically.
  • Over 50% of the Fortune 100 companies are current customers of Dynatrace.
Compensation and Rewards
  • We offer attractive compensation packages and stock purchase options with numerous benefits and advantages.
  • Due to legal reasons, we are obliged to list a salary range for this position, which is €74,000 up to €112,000 gross per year based on full-time employment (38.5 h/week). We’ve listed the salary range for transparency, but if your experience and skills bring unique value, we’d still love to hear from you—please apply even if you’re outside the range.
Equal Employment Opportunity

Dynatrace provides equal employment opportunities to all employees and applicants without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected characteristic. We actively foster an inclusive workplace that celebrates differences and promotes accessibility, collaboration, and growth for all.

Skills Required

  • 5+ years (Senior) or 10+ years (Principal) of professional software engineering experience
  • Demonstrated experience shipping production systems that use LLMs, including prompting, tool calling, evaluation, and iteration
  • Strong foundation in developer tooling, AI/ML engineering, or large-scale distributed systems
  • Hands-on experience with agentic patterns: planning, tool use, retrieval, memory management
  • Ability to evaluate and critique AI-generated output
  • Clear communication with cross-functional partners across product and engineering
  • Background in observability, APM, or infrastructure monitoring
  • Familiarity with engineering platforms at scale: CI/CD systems, developer portals, internal tooling
  • Hands-on experience with LLMs: prompt engineering, evaluation frameworks, or agent frameworks

What the Team is Saying

Michael Polter
Jamie Mallett
Trevor Ealy
Hannah Fleming
Kristen Hanlan

Dynatrace Compensation & Benefits Highlights

  • Leave & Time Off Breadth The package includes paid time off, parental leave, quarterly company‑wide Wellness Days, and volunteer time off; U.S. materials also describe an “unlimited PTO” model.
  • Healthcare Strength Comprehensive medical, dental, and vision coverage is paired with mental‑health support via an Employee Assistance Program, with U.S. pages emphasizing strong health benefits.
  • Retirement Support U.S. offerings highlight a 401(k) retirement plan and broader retirement savings support that contribute to long‑term financial security.

Dynatrace Insights

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The Company
HQ: Boston, MA
5,600 Employees
Year Founded: 2005

What We Do

Dynatrace lets customers understand their business like never before, so they can see beyond the complexity, find and fix problems faster and automate manual tasks with Al — so they can focus on what truly matters: running their business.

Why Work With Us

In a world that runs on software, our Al-driven insights cut through the noise, allowing you to focus on what truly matters by automating manual tasks and resolving issues with pinpoint accuracy. Our culture, fueled by curiosity, openness, and authenticity, drives our pursuit of innovation and excellence in crafting the Dynatrace platform.

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About our Teams

Dynatrace Offices

Hybrid Workspace

Employees engage in a combination of remote and on-site work.

Majority of roles are hybrid with flexibility. Please speak with our recruiting team for specific details on hybrid work.

Typical time on-site: 2 days a week
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