Ottimate

Ottimate, formerly known as Plate IQ, offers AP Automation AI Software that revolutionizes the invoice lifecycle with detailed GL mapping and deep learning AI. Their solutions cover End to End AP Automation, Invoice Automation, Payment Automation, and ...

IT Services

Information Technology

$164M raised

7 open positions

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Director of AI Engineering

3 months, 1 week ago

United States

Full-time

Executive

AI Engineer

Software Development

AWS Celery Machine Learning PostgreSQL Python REST API

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Ottimate

IT Services

$164M raised

View All Jobs 7

Description

Architect and ship production AI/ML systems for invoice understanding, vendor intelligence, conversational AP assistance, and autonomous AP agents.
Own the AI roadmap end-to-end, including prioritization, technical trade-offs, and delivery.
Set technical standards for model quality, evaluations, observability, reliability, and production readiness.
Write code, review code, and make hands-on architectural decisions alongside the team.
Drive adoption of agentic coding tools and measure improvements in team PR throughput.
Partner with Platform Engineering on infrastructure, data pipelines, and APIs.
Manage a distributed team of 8–10 engineers across Data and ML disciplines.
Hire, develop, and retain engineers while building a high-trust remote culture.
Partner with Product and customer-facing teams to sequence roadmap work and close feedback loops on model quality.
Own model performance metrics, evaluation frameworks, and continuous improvement pipelines across the full ML lifecycle.

Requirements

5+ years of experience in applied AI, machine learning, or related engineering leadership roles.
Experience building production agentic pipelines using frontier models such as Anthropic SDK or OpenAI SDK.
Hands-on experience with tool use, function calling, and multi-agent orchestration.
Experience designing reliable agent loops, including planning, memory, tool execution, and error recovery.
Experience building RAG pipelines, including chunking, embeddings, retrieval tuning, and reranking.
Experience creating evaluation frameworks from scratch, including correctness, regression, and semantic similarity measures.
Experience with observability for production AI, including tracing, cost tracking, latency, and failure analysis.
Experience fine-tuning frontier or open-source models using LoRA, QLoRA, or instruction tuning.
Strong hands-on Python and PostgreSQL experience, including schema design, query optimization, and indexing.
Experience with distributed systems, async workers, queues, retries, and state machines; Celery or similar frameworks is a bonus.
Experience designing public-facing REST APIs and developer-friendly versioning.
Experience building MCP servers or tool-accessible APIs for AI agent integration.
Experience with AWS or comparable cloud infrastructure for deploying AI workloads.
Prior startup or growth-stage leadership experience is preferred, along with finance/AP or hospitality domain experience.

Benefits

Competitive salary of $200,000-$225,000 plus a 15% annual bonus.
Medical, dental, vision, and other company-subsidized benefits for employees and their families.
Employer-sponsored 401(k) with company match.
Paid time off, with explicit encouragement to use it.
Annual company retreats.
Promotion-from-within culture.
Remote work in the United States only.
Opportunity to work at a high-scale startup with meaningful ownership and strong professional growth.

Interested in this position?

Apply directly on the company website

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