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Head of AI and Machine Learning Engineering

Denver, CO;San Francisco, CA;New York, NY;Los Angeles, CA;Seattle, WA;Toronto, Ontario, CAN - Remote💼 Full-time💰 $275,000–$305,000🗓 2026-05-22 → 2026-07-31

Core

Lead the strategy and execution of AI/ML systems to automate complex work, improve customer experiences, and support decision-making for small businesses.

Role type

Senior technical executive (Head of AI/MLE)

Builds

End-to-end AI/ML systems, ML platforms, and risk modeling capabilities for small business workflows.

Domain

Fintech / Small business HR & Payroll

Deliverable

production ML models | product features | infrastructure

Required skills

Strategic leadership of AI/ML organizations, classical ML and GenAI/LLM expertise, production-scale deployment, software engineering and systems background, platform tooling and guardrails, executive-level investment judgment, cross-functional influence.

Preferred skills

Fintech or regulated environment experience, advanced degree in CS/Data Science.

Technologies

Classical ML, GenAI/LLMs, statistical modeling, risk modeling, retrieval, agents, observability.

Responsibilities

Define and execute AI/ML systems strategy, partner with senior leaders to identify customer value, shape AI-native product building, develop ML platform capabilities, drive technical judgment on investments, set KPIs for AI/ML performance, stay current on AI/ML advancements.

Seniority

Executive (VP/Director level), hands-on strategic leadership

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