Director of Engineering, Cover Whale
$186.1-260k
Offers annual discretionary bonus opportunity
3+ days a week in office
Commercial truck insurance provider
Be an early applicant
Commercial truck insurance provider
101-200 employees
Be an early applicant
$186.1-260k
Offers annual discretionary bonus opportunity
3+ days a week in office
101-200 employees
Company mission
Cover Whale's mission is to leverage data, technology and industry expertise to efficiently reduce insurance costs and improve safety within the commercial trucking industry.
Role
Who you are
- 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 delive
What the job involves
- 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
- 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
- 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
- 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
- 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
- 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
Our take
Every commercial trucker requires insurance before they can start working, and this can get expensive for businesses that manage large-scale trucking fleets. Despite this insurance spend, commercial trucking fleets still cost businesses enormous amounts of money in road accidents, presenting significant room for improvement in insurance coverage plans.
Cover Whale provides insurance coverage for commercial trucking fleets, leveraging technology to collect hundreds of data points to help identify risks and reduce costs. Whilst the company faces intense competition from other insurance companies, Cover Whale's technology-first approach gives it an edge in providing faster quotes at lower rates compared to its rivals. So far it has driven more than $400 million in premiums through its insurance platform.
Cover Whale currently provides coverage throughout nearly all of the continental United States, with near-term plans to extend into the remaining territories. It is currently working to improve its product by forming strategic partnerships to help improve the accuracy of its platform and drive down insurance costs further by using its technology to incentivise safe driving.
Freddie
Company Specialist at Welcome to the Jungle
Company
Funding (2 rounds)
May 2024
$13.8m
EARLY VC
Oct 2021
$15.5m
SEED
Total funding: $29.3m
Company benefits
- Hybrid Work Model
- Matching 401k Plan
- Unlimited Vacation Policy
- Generous Parental Leave Program
- Employer Paid Life Insurance and AD&D
- Medical/Dental/Vision Insurance
- Short/Long Term Disability
- Employee Assistance Program
- Parental Coaching
Company HQ
Financial District, New York, NY
Leadership
Daniel Abrahamsen
(CEO)Experience working as Project Manager for Allied World from 2015 to 2019. Partner of UnderwritingCloud since 2013.
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