Director of Engineering

Cover Whale is redefining what insurance can be—smarter, safer, and powered by real-time data and technology that puts drivers first. As we accelerate toward our bold 2.0 vision in 2025, we’re hiring a Director of Engineering to lead our tech teams and help shape the future of insurance through scalable, high-impact engineering.

Who is Cover Whale?

Cover Whale improves road safety by combining the insurance products we sell with our data-driven driver coaching and safety program. Our safety program is proven to save lives while delivering better insurance for our drivers. Recently acknowledged in Forbes as one of America's Best Startup Employers 2023 (forbes.com). 

We provide easy insurance options for our drivers at industry-leading insurance loss ratios for the insurance companies that support Cover Whale. The Commercial Auto and Trucking segment of the insurance industry badly needs our help, and so do the hard-working drivers who have been struggling with ever-increasing insurance costs year after year. Join us in the mission!

The Role

The Director of Engineering will lead the engineering team, guiding the technical leads and developers in achieving the department’s goals. With strategic alignment and guidance from the CTO, technical guidance from the Chief Architect, product goals alignment with the product team, and a timeline and milestones alignment with the project team, the Director drives the execution of small to large initiatives with an eye towards timely delivery and quality. 

Key Responsibilities:

1. Leadership & Management
• Lead, mentor, and manage a team of engineering leads, ensuring they have the resources, support, and guidance to drive the performance and delivery of their respective teams.
• Foster a collaborative and results-oriented engineering culture that emphasizes high standards, productivity, and continuous improvement.
2. Team Productivity & Development
• Ensure engineering teams consistently deliver high-quality, scalable software on time and within scope.
• Monitor and improve team productivity metrics, implementing processes that enhance efficiency and reduce bottlenecks.
• Drive adoption of best practices in agile methodologies, code quality, and testing, fostering a culture of accountability and reliability.
3. Strategic Alignment & Execution
• Collaborate closely with the CTO, Chief Architect, Product, and UX organizations to translate architectural direction into actionable plans for the engineering teams.
• Ensure technical initiatives align with the Department’s broader business goals, keeping engineering efforts focused on delivering value to the organization and its customers.
• Identify, track and prioritize technical debt, balancing long-term architecture improvements with immediate business needs.
• Represent the engineering organization in building milestones and delivery/project plans to help deliver value to the organization. 
• Commitment to providing constructive, solution-oriented feedback across the CTO organization.
4. Technical Oversight
• Work with the Chief Architect to ensure adherence to architectural standards and best practices across all engineering teams.
• Guide engineering leads in developing solutions that meet performance, scalability, and security requirements.
• Oversee key engineering projects, providing guidance on technical challenges and ensuring milestones are met.
5. Cross-Functional Collaboration
• Serve as a primary point of contact between the engineering department and other stakeholders, ensuring transparency and effective communication.
• Partner with product management to align on feature prioritization, timelines, and resourcing needs.
• Coordinate with QA, UX, Project Management, and other departments to streamline the release process, ensuring smooth deployments and high-quality releases.

Experience/Skills Required: 

• Proven ability to prioritize and deliver in fast-paced, evolving environments.
• Experience in or understanding of the insurance industry or adjacent regulated environments (strongly preferred).
• Familiarity with telematics, data platforms, or IoT solutions is a plus.

• Minimum of 8 years experience in software engineering
• 5–10+ years of experience leading software engineering teams, including engineering managers or tech leads.
• Proven track record of mentoring and developing high-performing, cross-functional global teams.
• Strong people management skills with a focus on collaboration, productivity, and accountability.
• Hands-on experience with scalable software architecture, systems design, and engineering best practices.
• Deep understanding of cloud infrastructure, APIs, and secure software development practices.
• Strong communication skills and the ability to work effectively with Product, UX, QA, and Executive teams.
• Ability to represent engineering in roadmap planning and milestone delivery.

At Cover Whale, we believe in transparent and equitable compensation practices. The expected base pay for this role is:

• Remote: $186,100 – $240,000 per year
• Hybrid (in-office attendance required at least 3 times per week): $195,000 – $260,000 per year

Final base pay is determined based on several factors, including skills, experience, and geographic location. Base pay is only part of our total compensation package, which also includes:

• Annual discretionary bonus opportunity
• Comprehensive health, dental, and vision insurance
• 401(k) with company match up to 4 %
• Generous paid time off and company holidays
• Wellness benefits and professional development support.

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.