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Ledgebrook

Modernizing the Specialty insurance industry

Director – Data & AI Engineering

Data EngineerData EngineerFull TimeRemoteSeniorTeam 51-200Since 2021H1B No SponsorCompany SiteLinkedIn

Location

California

Posted

4 days ago

Salary

$200K - $250K / year

Seniority

Senior

Bachelor Degree8 yrs expEnglishAirflowPythonSQLTerraform

Job Description

Director – Data & AI Engineering

Ledgebrook

• Manage, mentor, and grow a 10-person data engineering team and a 3-person AI/ML team; own headcount planning and hiring across both • Set a unified roadmap where data infrastructure and AI/ML development reinforce each other • Build a culture of technical rigor, ownership, and delivery • Lead development of ML models using proprietary insurance data: risk scoring, pricing signals, anomaly detection, loss prediction • Own LLM integration strategy from prompt engineering and RAG pipelines to fine-tuning and agentic workflows • Drive AI automation across operations: underwriting intake, document processing, triage, internal tooling • Partner with the CTO on enterprise AI platform decisions: tooling, deployment infrastructure, model governance • Build the evaluation, monitoring, and feedback loops that turn experiments into production systems • Set architectural standards for pipelines, data modeling, and platform infrastructure • Own reliability, observability, and data quality across Snowflake, dbt, Airflow, and Terraform • Build semantic layers and data models that serve underwriting, pricing, finance, and executive reporting • Establish data governance, quality frameworks, and documentation standards that scale • Collaborate with actuaries, underwriters, engineers, and product leaders to translate business needs into AI and data solutions • Operate as a senior technical voice in planning, roadmap, and strategy discussions

Job Requirements

  • Required 8+ years across data engineering, ML engineering, or AI/data science with meaningful depth in at least two of those
  • 3+ years managing technical teams, with experience leading both data and ML/AI practitioners
  • Hands-on fluency in Python and SQL; comfort reviewing production ML code and data pipelines
  • Experience building and deploying ML models against structured business data (pricing, risk, fraud, or equivalent)
  • Production experience with LLMs - RAG architectures, prompt design, agentic frameworks, or fine-tuning
  • Strong grounding in modern data stack tooling (Snowflake, dbt, Airflow, Terraform or equivalents)
  • History of taking AI/ML work from prototype to reliable production system
  • Experience in insurance, fintech, or other data-rich regulated domains (Nice to Have)

Benefits

  • Full remote flexibility and asynchronous work culture
  • Unlimited PTO and fully paid sick leave
  • Comprehensive health benefits, including medical, dental, and vision coverage, plus HSA and FSA options
  • Additional financial protection and retirement benefits, including a 401(k), company-paid life insurance, and disability coverage
  • A high degree of ownership, autonomy, and the opportunity to help build and shape a growing company
  • The chance to make a meaningful impact while working alongside an ambitious, high-performing team
  • Exposure to the challenges and opportunities of a fast-growing startup environment

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