Senior AI Engineer

About Senior AI Engineer at Underdog.io

Underdog.io is a fast-growing automation startup backed by top-tier investors. Our mission is to transform how Managed Service Providers (MSPs) work by eliminating mundane tasks through intelligent tools.

What You’ll Do

• Design and ship AI features that solve real MSP pain points including natural-language workflow creation, autonomous agents, and context-aware task automation.
• Build agentic systems that act responsibly—automate tasks, ask for input, or escalate to humans when necessary.
• Optimize production-grade AI using prompt tuning, RAG pipelines, and inference stacks (OpenAI, Claude, open-source LLMs) for speed, cost, and reliability.
• Integrate AI into core workflows utilizing tools like LangChain, LlamaIndex, and custom orchestration layers.
• Collaborate cross-functionally to transform prototypes into features that ship.
• Solve complex challenges by balancing autonomy with safety, reducing hallucinations, and embedding empathy into AI interactions.

Tech Stack You’ll Use

• Core: Python, FastAPI, Celery, PostgreSQL, React
• AI/ML: OpenAI, Anthropic, Mistral/LLaMA, LangChain, Pinecone
• Infra: AWS/Azure, Kubernetes, Docker, Redis
• Observability: LLM telemetry, cost optimization

Who You Are

• 5+ years in software engineering with 2+ years shipping production AI/ML systems.
• Expert in LLM integration, prompt engineering, and building human-AI interaction patterns.
• Builder mindset who prioritizes user impact over model hype.
• Understands MSP pain points with bonus experience in RPA/automation.
• Excellent communication skills translating technical complexity into user value.

Above & Beyond

• Experience with fine-tuning or hosting open-source LLMs.
• Contributions to AI open-source projects, e.g., LangChain agents.
• Expertise in observability and cost optimization for AI inference.
• Background in automation and agent-based systems is a plus.

Why Join

• Solve meaningful problems by directly helping overworked IT engineers.
• Ownership & impact with autonomy on high-stakes AI decisions.
• Competitive compensation including salary, equity, and benefits.
• Remote-first culture collaborating with execution-focused teammates.
• No fluff, just shipping results.

Key skills/competency

• AI integration
• LLM
• Machine Learning
• Prompt Engineering
• Python
• FastAPI
• Cloud Infrastructure
• Automation
• DevOps
• Collaboration