Director of AI Engineering

Role Description

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.

What You'll Own

• 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

What You Won't Own

• Product direction, spec writing, or feature prioritization (that's the product management team's role)
• Pod-level delivery — the pod is PM + Engineer + AI Agents; you govern the platform they operate on
• Company-wide AI enablement and adoption (that's the AI Enablement Lead)

Qualifications

• 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

Preferred

• 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

Competencies

• Complexity of Work: Grasps the complexity of work items communicated by any level of engineer. Expertly supports the team and drives the priority of engineering work.
• Judgment & Decision-Making: Leverages deep management experience to bring maturity and thoughtfulness to decisions. Elevates collective judgment across the engineering department.
• Leadership: Balances leadership and management. Creates own work, mentors managers and engineers, and contributes to continuous improvement of the department.
• Communication: Communicates complex technical topics concisely to direct reports, peers, and senior leadership. Frames technical matters against business needs.
• Toolbox: Stays current with tools and evolving technologies. Drives strategic conversations by aligning technical concepts with business value. Stewards the company's finances by aligning team needs with budget.
• Expertise: Applies breadth of knowledge across operational initiatives. Ensures alignment among direct reports and manages information flow between departments.
• Core Values: Embodies Cover Whale's core values publicly and drives conversations to ensure managers convey these values to their teams.

Benefits

• Base salary ranging from $156,000.00 to $175,000.00 annually
• Annual discretionary bonus opportunity
• 401(k) company match up to 4%
• Comprehensive health (Blue Shield Blue Cross) with employer contribution up to 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