About The Role

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