Director of AI Engineering
About The Position
About the Role This is not a rebranded Director of Engineering. It is a new position purpose-built for a new way of building software. Cover Whale is operating an agentic engineering model where pods of product managers, engineers, and AI agents deliver production software together. The Director of AI Platform Engineering owns the platform those pods operate on — the agent orchestration layer, trust boundaries, human-in-the-loop controls, and evaluation pipelines that make it safe and effective to delegate work to AI at production scale. You will be a player-coach: hands-on building the platform while also leading and developing the engineering team. Your mandate is to ensure that humans and AI agents collaborate safely, reliably, and at velocity.
Requirements
- Seasoned engineering leadership with a thorough understanding of agentic workflows as they relate to agentic software engineering
- Deep understanding 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
Nice To Haves
- Hands-on experience with Anthropic toolsets such as Claude Code and associated Claude tooling
- Background in insurtech, fintech, or other regulated industries where compliance and security oversight are table stakes
- Experience implementing evaluation and observability pipelines for AI-generated output
Responsibilities
- Agentic Platform Architecture
- Human-in-the-loop boundaries — setting trust thresholds where AI-generated output is auto-approved versus escalated for review
- Prompt and spec evaluation pipelines — the systems that validate whether AI-generated code, tests, and configurations meet production standards before reaching a human reviewer
- The end-to-end specification-through-deployment pipeline: how specs become agent instructions and how agent output becomes production code
- Evaluation and integration of emerging AI tooling, models, and agent frameworks
- Engineering System Integrity
- Quality gates calibrated for AI-augmented velocity — ensuring AI-generated output meets production standards
- Engineering standards: branch protection, test coverage, CI/CD rules, and deployment integrity
- Architectural escalation path for engineers facing technical blockers
- Collaboration with the Technical Program Leader on engineering flow patterns and systemic bottlenecks
- People Leadership for an Agentic Team
- Coaching engineers through the identity shift from "I write code" to "I orchestrate AI agents and own outcomes"
- Career development, performance accountability, and 1:1s — with expectations calibrated to the expanded role of delegate, review, and own
- Building team culture where engineers treat AI agents as force multipliers, not threats
Benefits
- 401(k) company match up to 4 %
- Comprehensive health (Blue Shield Blue Cross) with employer contribution up top 100%, dental, and vision insurance
- Maternity & Paternity Leave
- Gym Reimbursement up to $400 per year
- Professional education reimbursement up to $500 per year
- Generous paid time off and company holidays
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What This Job Offers
Job Type
Full-time
Career Level
Director
Education Level
No Education Listed
Number of Employees
11-50 employees
