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Director of AI Engineering

7 hours, 20 minutes ago
United States
Full-time
Executive
AI Engineer
Software Development
CI/CD
Apply Now
Cover Whale

Cover Whale

Cover Whale | Truck Insurance, Hotshot Trucking, UIIA, Get Appointed Insurtech for commercial truck insurance, saving wholesale and retail insurance agents time & hassles. Get your fast estimates and binders now! Seasoned insurance executive brings nea...

Insurance
51-250
Founded 2019
View All Jobs 7

Description

  • Own the agent orchestration platform used by engineering pods to deliver production software.
  • Design human-in-the-loop boundaries and trust thresholds for AI-generated work.
  • Build prompt and spec evaluation pipelines for code, tests, and configuration outputs.
  • Oversee the end-to-end specification-through-deployment workflow from agent instructions to production code.
  • Evaluate and integrate emerging AI tooling, models, and agent frameworks.
  • Maintain engineering system integrity through branch protection, test coverage, CI/CD rules, and deployment controls.
  • Set quality gates that balance AI-augmented velocity with production standards.
  • Provide escalation support for engineers facing technical blockers and technical workflow issues.
  • Partner with the Technical Program Leader to improve engineering flow patterns and remove systemic bottlenecks.
  • Coach and develop engineers, including performance management, 1:1s, and career growth.
  • Build a team culture where AI agents are treated as force multipliers and outcomes are owned by the team.

Requirements

  • Seasoned engineering leadership experience with a strong understanding of agentic workflows in software engineering.
  • Deep knowledge of CI/CD, quality assurance automation, and deployment integrity in high-velocity environments.
  • Track record of leading engineering teams through significant technology or process transformations.
  • Ability to architect trust and permission models for systems where automated agents produce production artifacts.
  • Hands-on experience with Anthropic toolsets such as Claude Code and related Claude tooling is preferred.
  • Background in insurtech, fintech, or other regulated industries is preferred.
  • Experience implementing evaluation and observability pipelines for AI-generated output is preferred.
  • Strong ability to communicate complex technical topics concisely to direct reports, peers, and senior leadership.
  • Ability to balance leadership and management responsibilities, mentor engineers and managers, and drive continuous improvement.
  • Comfort operating in a fast-paced, high-pressure startup environment.

Benefits

  • Base salary range of $156,000 to $234,000 annually.
  • Annual discretionary bonus opportunity.
  • 401(k) company match up to 4%.
  • Comprehensive Blue Shield Blue Cross health coverage with employer contribution up to 100%, plus dental and vision insurance.
  • Maternity and paternity leave.
  • Gym reimbursement up to $400 per year.
  • Professional education reimbursement up to $500 per year.
  • Generous paid time off and company holidays.

Interested in this position?

Apply directly on the company website

Apply Now

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