Underwriting Associate I/Customer Service Representative

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.

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

As an Underwriting Associate 1, you will be the first point of contact for policyholders and agents, providing essential phone support and assisting with general underwriting and service-related inquiries.

This role is ideal for a detail-oriented professional looking to gain experience in underwriting, policy servicing, and customer support. You will be responsible for answering inbound inquiries (by phone and/or email) quickly and efficiently, ensuring first-call resolution whenever possible, and maintaining high-quality service standards.

Key Responsibilities:

• Assist customers with policy details, billing inquiries, endorsements, and general coverage questions.
• Support policy renewals by providing clear explanations and guidance.

• Maintain a high level of accuracy in all underwriting and policy-related communications.

• Demonstrate a foundational understanding of underwriting, billing, DriveSmart, and cancellations/reinstatements.
• Develop proficiency in Cover Whale’s knowledge base, binding, billing, cancellation, and reinstatement processes.
• Ensure quality responses that deepen customer relationships and minimize the need for follow-up inquiries.
• Work closely with the DriveSmart, Underwriting and Billing teams to ensure smooth handling of customers’ needs.

Requirements

Qualifications & Experience

• 1+ years of insurance experience, preferably in underwriting or policy servicing.
• Strong customer service and phone communication skills, with experience handling complex insurance inquiries.
• Proficiency in business applications like Zendesk, HubSpot, Slack, and Excel.
• Strong problem-solving skills and ability to work in a fast-paced, team-oriented environment.
• Spanish fluency is a bonus but not required.

Benefits

The anticipated base salary for this position will be between $52,232.80 and $66,000 per year for remote candidates at the beginning of employment, and between $62,000 and $70,000 for hybrid positions in New York. However, the base salary will be determined on an individualized basis, taking into account factors such as geographical location within the United States and relevant experience. Additionally, the base salary constitutes only one component of the overall compensation package, which also includes a discretionary bonus and various benefits sponsored by Cover Whale.

Perks/Benefits:

• Health Care Plan (Medical, Dental & Vision)
• Retirement Plan (401k, IRA)-4% match
• Life Insurance (Basic, Voluntary & AD&D)
• Paid Time Off (Vacation, Sick & Public Holidays)
• Paid Family Leave (Maternity, Paternity)
• Tuition Assistance
• Professional Training & Development

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.