Director of Engineering

Cover Whale is redefining what insurance can besmarter, safer, and powered by real-time data and technology that puts drivers first. Cover Whale improves road safety by combining the insurance products we sell with our data-driven driver coaching and safety program, which is proven to save lives while delivering better insurance for our drivers. 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.

The Role

The Director of Engineering is a two-part role: be the Solutions Architect for the team, be the technical lead(er) for the organization. In addition, this role plays a key part in ensuring the teams are working together to solve problems

The Solutions Architect part of the role allows you to build the bridge between big picture architecture and the solutioning of the actual problem at hand, and allows the team to understand the HOW and the WHY. As a Technical Lead(er), you will provide hands-on guidance to the engineering organization from a coding, technical problem-solving, implementation, and prioritization standpoint. You will work directly with Product, UX, QA, Infrastructure, DevSecOps, and other teams to ensure the engineering team can commit and deliver to the needs of the organization. This role requires hands-on coding skills and deep experience in GoLang and Vue.js (or other equivalent frameworks). Other skills: AWS / cloud native application development, Python, NATS.io, fly.io, Pulumi.

Key Responsibilities:

1. Technical Oversight
• Solve the hardest coding and technical problems to pave the way for the team.
• Build the architecture in partnership with the Chief Architect and adjust as the project parameters evolve.
• Guide engineering leads in developing solutions that meet performance, scalability, and security requirements.
2. Team Productivity & Development
• Work in partnership with the Product team to prioritize and manage the work for the teams, ensure LOE and ETAs are built and fed into the larger plan, and hold the teams accountable for delivery.
• Proactively provide clarity and visibility into delivery on an ongoing basis.
• Monitor and improve team productivity metrics, implementing processes that enhance efficiency and reduce bottlenecks.
3. 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.
4. Strategic Alignment & Execution
• 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.
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

Requirements

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
• 510+ 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.

Benefits

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.

Qualification

Bachelor's Degree