Director of AI Engineering

Join Ottimate, a company revolutionizing accounts payable with AI technology. As the Director of AI Engineering, you will lead the AI and ML layer of our product, manage a distributed team of engineers, and drive technical decisions. This is a hands-on leadership role where you will spend at least half your time writing code and architecting systems. You will also set the AI roadmap, partner with cross-functional teams, and communicate AI capabilities to non-technical stakeholders.

• Architect and ship production AI/ML systems, writing code and driving technical decisions.
• Own the AI roadmap end-to-end, prioritizing, making trade-offs, and ensuring delivery.
• Manage a distributed team of engineers across Data and ML disciplines, hiring, developing, and retaining talent.
• We are looking for a senior technical manager or director — ideally someone who has thrived at a smaller company and is ready for a career step up into broader ownership
• If you are energized by shipping real AI products, working with noisy real-world financial data, and building the systems that will define how enterprises automate AP, this role is for you
• OpenAI SDK
• Production agentic pipelines using frontier models

Anthropic SDK

• Production agentic pipelines using frontier models
• Anthropic SDK
• Reliable agent loop design — planning, memory, tool execution, error recovery
• Tool use, function calling, multi-agent orchestration
• RAG pipeline design — chunking, embedding models, retrieval tuning, reranking
• Evals frameworks built from scratch — correctness, regression, semantic similarity
• Observability for production AI — tracing, cost tracking, latency, failure analysis
• Model selection trade-offs — cost, latency, capability, context window
• LoRA, QLoRA, instruction tuning — not just off-the-shelf API calls
• Training data collection, curation, cleaning, and labeling at scale
• Fine-tuning frontier or open-source models for domain-specific tasks
• LLM inference and serving optimization
• VLLM, TGI, or equivalent
• AWS or cloud infrastructure — enough to own AI workload deployment
• Hands-on Python — comfortable writing, reviewing, and shipping production code
• PostgreSQL — schema design, query optimization, indexing strategies
• Distributed systems — async workers, queues, retries, state machines
• Public-facing API design — REST, versioning, developer experience
• MCP server development — tool-accessible APIs for AI agent integration
• Celery or similar async task frameworks is a bonus
• Engineering Manager ready for director-level ownership
• Comfortable owning outcomes
• Has led technical teams at a startup or growth-stage company — knows how to move fast
• Hands-on contributor who has also managed small high performance teams
• Finance and/or AP domain — invoice workflows, GL coding, vendor management
• Hospitality — high-volume, multi-location AP operations
• Noisy, unstructured text data — OCR outputs, inconsistent supplier formats, entity resolution at scale
• Exceptional AI engineering skills are the primary bar. We will teach the domain