Senior AI Engineer

The way code gets written has changed more in the last year than in the previous twenty. Maestro is the platform engineering leaders use to navigate this transition — helping teams adopt AI deliberately, hold their craft to a higher standard, and turn the moment into a durable advantage instead of a missed one.

As an early-stage, venture-backed startup, joining our team means you’ll play a critical role in shaping our product and company culture. You’ll have the opportunity to design and deliver customer-facing features, address critical customer issues, and contribute to our technical and operational foundations from day one. We are a Seattle-based company, biased toward in-person collaboration, but open to fully remote for the right candidates.

The role

As a Senior AI Engineer at Maestro, you’ll be responsible for:

• Develop AI solutions. As a senior AI engineer, you’ll lead the development of the models, evals, and pipelines that power Maestro’s reporting and insights. You’ll work closely with product to integrate them seamlessly.
• Build product and infrastructure. You’ll shape architectural decisions that let our AI systems scale with the customer base — and the AI landscape — as both move quickly.
• Enhance product features. You’ll improve and expand our AI-driven features, making sure they deliver accurate, actionable insights. Your work directly impacts how engineering leaders manage their teams.
• Engage with customers. You’ll help triage AI-related customer issues and provide technical guidance, ensuring users have the best experience with our AI capabilities.
• Help us grow the team. As an early AI hire, you’ll be instrumental in recruiting, hiring, and developing new talent.
• Pioneer the eval framework for agentic coding sessions. What separates a 12-turn verified session from a 90-turn vibe-coding sprawl — and how do we score it reliably?
• Revolutionize AI-driven insights. Elevate Maestro to deliver cutting-edge reporting that empowers organizations to make smarter, faster decisions.
• Develop AI Narratives that read like a sharp staff engineer wrote them. Synthesis a VPE will read in five minutes and trust.
• Build hallucination-resistant verification pipelines. We say things about real engineering work in front of real engineering leaders. We don’t get to make things up.
• Build scalable systems that handle the growing demands of an expanding customer base — and the demands of LLM systems that get more capable every quarter.

If this is you, let’s talk:

• 5+ years of AI engineering experience, with a strong track record building robust, scalable AI systems.
• Expertise in AI and NLP. Extensive experience with natural language processing, machine learning, and integrating with APIs like OpenAI, Anthropic, and Google Gemini.
• Backend experience using Python or Node.js.
• Familiarity with AWS (ECS, EC2, SQS, Lambda, S3).
• You’ve shipped LLM systems that engineers stake their judgment on. You know what it takes to get model output to that bar.
• Customer-focused mindset. You take pride in building products people love and solving real customer problems.
• Ownership mentality. You understand customer problems and have the autonomy to find the best solutions.
• Collaborative approach. You love working cross-functionally to achieve great customer outcomes and contribute to our culture.
• Experience building eval frameworks or LLM-as-judge systems
• Experience with retrieval, agents, or long-context applications
• Experience leading or mentoring a team
• Based in Seattle

Compensation

Base salary $150,000–$190,000, plus generous early-employee equity and benefits. Final offer depends on skills, experience, and education. Equity at this stage is a real part of the package, not a footnote.