Director of AI Engineering

Location: Remote - United States only.About the role:Ottimate is building the AI-native future of accounts payable. Our platform processes millions of invoices across hundreds of enterprise customers, powered by a suite of ML models and agentic workflows. As Director of AI Engineering, you will own the full AI and ML layer of our product — from invoice understanding and vendor intelligence to our conversational AP Copilot and the next generation of autonomous AP agents.This is a hands-on leadership role. You will spend at least half your time writing code, architecting systems, and driving technical decisions alongside your team. You will also set the AI roadmap, partner cross-functionally with Product, Data, and Platform Engineering, and manage a distributed team of 8–10 engineers across Data and ML.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.ResponsibilitiesTechnical LeadershipArchitect and ship production AI/ML systems — you write code, not just review itOwn the AI roadmap end-to-end: prioritization, trade-offs, deliverySet technical standards for model quality, evals, observability, and reliabilityDrive adoption of agentic coding tools to multiply team velocityClaude Code, Cursor, Copilot, or equivalent — measure and improve PR throughputPartner with Platform Engineering on infrastructure, data pipelines, and APIsPeople & Cross-FunctionalManage a distributed team of 8–10 engineers across Data and ML disciplinesHire, develop, and retain engineers at all levels; build a high-trust remote culturePartner with Product on roadmap sequencing and scope trade-offsWork directly with customer-facing teams to close feedback loops on model qualityCommunicate AI capabilities and limitations clearly to non-technical stakeholdersModel & Systems OwnershipOwn model performance metrics and drive continuous improvement pipelinesBuild and maintain evals frameworks — regression suites, human review, A/B testingOversee training data collection, curation, and labeling operationsManage the full ML lifecycle: experimentation, deployment, monitoring, iterationDefine and enforce quality bars for agentic workflows entering productionRequirementsApplied AI & Agentic SystemsProduction agentic pipelines using frontier modelsAnthropic SDK · OpenAI SDK · tool use, function calling, multi-agent orchestrationReliable agent loop design — planning, memory, tool execution, error recoveryRAG pipeline design — chunking, embedding models, retrieval tuning, rerankingEvals frameworks built from scratch — correctness, regression, semantic similarityObservability for production AI — tracing, cost tracking, latency, failure analysisModel ExpertiseFine-tuning frontier or open-source models for domain-specific tasksLoRA, QLoRA, instruction tuning — not just off-the-shelf API callsTraining data collection, curation, cleaning, and labeling at scaleLLM inference and serving optimizationvLLM, TGI, or equivalent Model selection trade-offs — cost, latency, capability, context windowEngineering DepthHands-on Python — comfortable writing, reviewing, and shipping production codePostgreSQL — schema design, query optimization, indexing strategiesDistributed systems — async workers, queues, retries, state machinesCelery or similar async task frameworks is a bonusPublic-facing API design — REST, versioning, developer experienceMCP server development — tool-accessible APIs for AI agent integrationAWS or cloud infrastructure — enough to own AI workload deploymentsIdeal Career BackgroundEngineering Manager ready for director-level ownershipHas led technical teams at a startup or growth-stage company — knows how to move fastHands-on contributor who has also managed small high performance teams.Comfortable owning outcomes ★ Industry ExperienceFinance and/or AP domain — invoice workflows, GL coding, vendor managementHospitality — high-volume, multi-location AP operationsNoisy, unstructured text data — OCR outputs, inconsistent supplier formats, entity resolution at scale★ Industry experience above is a bonusExceptional AI engineering skills are the primary bar. We will teach the domain.BenefitsWe care deeply about making Ottimate an incredible place to work and invest a significant amount of time and energy into creating and maintaining a company culture that provides our team with a generous level of support whilst inspiring them to do their best work. The specific benefits/perks we offer are continually evolving, but currently include:Compensation: 200,000-225,000 + 15% Annual Bonus + EquityCompetitive salary based on skills & experience.Medical, Dental, Vision and other Company-Subsidized Benefits for you and your family.Employer sponsored 401(k) with company match.Paid Time Off (and the encouragement to use it).Annual company retreats.Promote from within philosophy.Beyond the tangible benefits though:You will be part of a growing team, at a pinnacle moment of scale for the business, and experience the excitement of working in a startup where each action makes a huge difference.You will have the agency to solve difficult problems creatively, the freedom to explore work that inspires you, and infrastructure to ensure you're constantly challenged and developing.You will work with sharp, passionate teammates solving some of the most unique challenges and positioning our product as a premier finance automation solution. Our commitment to empowering a diverse and inclusive workforce, celebrating differences, and creating a safe space for our employees to bring their whole selves to work is second to note.We are transforming entire industries using innovative technology including Artificial Intelligence, Payment Tech, and Neural Networks.Our leaders lead with a people-first approach; inspiring excellence, nurturing ideas, and finding creative ways to eliminate obstacles for cultivating growth.We truly love what we do and who we do it with - and we think you will too!Ottimate is an equal opportunity employer that is committed to diversity and inclusion. We do not discriminate based on race, color, national origin, religion, gender, gender expression, sexual orientation, age, veteran status, disability status, or marital status. If you are excited about the role but do not meet 100% of the qualifications listed above, we encourage you to apply. Nothing in this job posting should be construed as an offer or guarantee of employment.This job description is intended to describe the general nature and level of work being performed by employees assigned to this position. It is not intended to be an exhaustive list of all duties, responsibilities, qualifications, or working conditions associated with the position. Employees may be required to perform other job-related duties as assigned to meet business needs. Nothing in this job description creates a contract of employment, alters the at-will employment relationship where applicable, or guarantees any specific terms or conditions of employment. The Company reserves the right to modify this job description at any time, with or without notice, subject to applicable federal, state, and local law.

Location: Remote - United States only.

About the role:

Ottimate is building the AI-native future of accounts payable. Our platform processes millions of invoices across hundreds of enterprise customers, powered by a suite of ML models and agentic workflows. As Director of AI Engineering, you will own the full AI and ML layer of our product — from invoice understanding and vendor intelligence to our conversational AP Copilot and the next generation of autonomous AP agents.

This is a hands-on leadership role. You will spend at least half your time writing code, architecting systems, and driving technical decisions alongside your team. You will also set the AI roadmap, partner cross-functionally with Product, Data, and Platform Engineering, and manage a distributed team of 8–10 engineers across Data and ML.

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.

Responsibilities

Technical Leadership

• Architect and ship production AI/ML systems — you write code, not just review it
• Own the AI roadmap end-to-end: prioritization, trade-offs, delivery
• Set technical standards for model quality, evals, observability, and reliability
• Drive adoption of agentic coding tools to multiply team velocity
• Claude Code, Cursor, Copilot, or equivalent — measure and improve PR throughput
• Partner with Platform Engineering on infrastructure, data pipelines, and APIs

People & Cross-Functional

• Manage a distributed team of 8–10 engineers across Data and ML disciplines
• Hire, develop, and retain engineers at all levels; build a high-trust remote culture
• Partner with Product on roadmap sequencing and scope trade-offs
• Work directly with customer-facing teams to close feedback loops on model quality
• Communicate AI capabilities and limitations clearly to non-technical stakeholders

Model & Systems Ownership

• Own model performance metrics and drive continuous improvement pipelines
• Build and maintain evals frameworks — regression suites, human review, A/B testing
• Oversee training data collection, curation, and labeling operations
• Manage the full ML lifecycle: experimentation, deployment, monitoring, iteration
• Define and enforce quality bars for agentic workflows entering production

Requirements

Applied AI & Agentic Systems

• Production agentic pipelines using frontier models
• Anthropic SDK · OpenAI SDK · tool use, function calling, multi-agent orchestration
• Reliable agent loop design — planning, memory, tool execution, error recovery
• 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 Expertise

• Fine-tuning frontier or open-source models for domain-specific tasks
• LoRA, QLoRA, instruction tuning — not just off-the-shelf API calls
• Training data collection, curation, cleaning, and labeling at scale
• LLM inference and serving optimization
• vLLM, TGI, or equivalent
• Model selection trade-offs — cost, latency, capability, context window

Engineering Depth

• 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
• Celery or similar async task frameworks is a bonus
• Public-facing API design — REST, versioning, developer experience
• MCP server development — tool-accessible APIs for AI agent integration
• AWS or cloud infrastructure — enough to own AI workload deployments

Ideal Career Background

• Engineering Manager ready for director-level ownership
• 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.
• Comfortable owning outcomes

★ Industry Experience

• 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

★ Industry experience above is a bonus

Exceptional AI engineering skills are the primary bar. We will teach the domain.

Benefits

We care deeply about making Ottimate an incredible place to work and invest a significant amount of time and energy into creating and maintaining a company culture that provides our team with a generous level of support whilst inspiring them to do their best work.

The specific benefits/perks we offer are continually evolving, but currently include:

• Compensation: 200,000-225,000 + 15% Annual Bonus + Equity
• Competitive salary based on skills & experience.
• Medical, Dental, Vision and other Company-Subsidized Benefits for you and your family.
• Employer sponsored 401(k) with company match.
• Paid Time Off (and the encouragement to use it).
• Annual company retreats.
• Promote from within philosophy.

Beyond the tangible benefits though:

• You will be part of a growing team, at a pinnacle moment of scale for the business, and experience the excitement of working in a startup where each action makes a huge difference.
• You will have the agency to solve difficult problems creatively, the freedom to explore work that inspires you, and infrastructure to ensure you're constantly challenged and developing.
• You will work with sharp, passionate teammates solving some of the most unique challenges and positioning our product as a premier finance automation solution.
• Our commitment to empowering a diverse and inclusive workforce, celebrating differences, and creating a safe space for our employees to bring their whole selves to work is second to note.
• We are transforming entire industries using innovative technology including Artificial Intelligence, Payment Tech, and Neural Networks.
• Our leaders lead with a people-first approach; inspiring excellence, nurturing ideas, and finding creative ways to eliminate obstacles for cultivating growth.
• We truly love what we do and who we do it with - and we think you will too!

Ottimate is an equal opportunity employer that is committed to diversity and inclusion. We do not discriminate based on race, color, national origin, religion, gender, gender expression, sexual orientation, age, veteran status, disability status, or marital status. If you are excited about the role but do not meet 100% of the qualifications listed above, we encourage you to apply. Nothing in this job posting should be construed as an offer or guarantee of employment.

This job description is intended to describe the general nature and level of work being performed by employees assigned to this position. It is not intended to be an exhaustive list of all duties, responsibilities, qualifications, or working conditions associated with the position. Employees may be required to perform other job-related duties as assigned to meet business needs. Nothing in this job description creates a contract of employment, alters the at-will employment relationship where applicable, or guarantees any specific terms or conditions of employment. The Company reserves the right to modify this job description at any time, with or without notice, subject to applicable federal, state, and local law.

Ottimate is an AI-powered AP [Accounts Payable] automation platform that empowers finance teams to reduce costs, prevent overpayments, detect fraud, and enforce policy compliance across the entire invoice-to-payment lifecycle.Ottimate provides a smarter way for AP managers, approvers, controllers, and CFOs to work through the entire invoice lifecycle. With mature deep learning capabilities, Ottimate gets to know your business and AP process down to the line-item, supporting a custom approval and payment workflow. Ottimate not only eliminates over 90% of the manual accounting process but also provides insights into invoices and spend, helping finance professionals uncover opportunities for growth. This means more strategic business decisions for CFOs and a better day-to-day for the entire team.

Ottimate is an AI-powered AP [Accounts Payable] automation platform that empowers finance teams to reduce costs, prevent overpayments, detect fraud, and enforce policy compliance across the entire invoice-to-payment lifecycle.

Ottimate provides a smarter way for AP managers, approvers, controllers, and CFOs to work through the entire invoice lifecycle. With mature deep learning capabilities, Ottimate gets to know your business and AP process down to the line-item, supporting a custom approval and payment workflow. Ottimate not only eliminates over 90% of the manual accounting process but also provides insights into invoices and spend, helping finance professionals uncover opportunities for growth. This means more strategic business decisions for CFOs and a better day-to-day for the entire team.