Director of AI Engineering

About the Role

We are looking for 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.

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.

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
  

Required

• 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.:

At Cover Whale, we are committed to fostering a culture of transparency and fairness in our compensation practices. For this position, you can expect a base salary ranging from $156,000.00 to $234,000.00 annually. The final salary will be influenced by various factors, such as your experience in the insurance sector, your unique skill set, and your location. It's important to note that base pay is just one element of our comprehensive compensation package, which also includes an annual discretionary bonus opportunity, in addition to:

• 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

At Cover Whale, we’re in the business of building the future of connected insurance. Our work is tough, deadlines are tight, and the startup road is bumpy. We expect dedication, agility, and a relentless drive to problem-solve. Not everyone is cut out for this pace or pressure, and that’s okay. But if you’re here, we expect your best. Every day. We succeed together, and we set the bar high. If you’re ready to push limits, join us!

Cover Whale works to maintain the best possible environment for our employees, where individuals can learn and grow with the company. We strive to provide a collaborative environment where each person feels encouraged to contribute to their processes, decisions, planning, and culture.

We are an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, or any other characteristic protected by law