Careers at Cover Whale

Shift your career into high gear.

Join the future of commercial trucking insurance.

Cover Whale has grown sustainably since our founding in 2019, and we’re looking for talented individuals to help us grow further and faster. And, our team is making our nation’s roads safer on a daily basis. Fact.

Benefits? Oh yeah, we've got 'em.

Hybrid Work Model

Flexible Paid Time Off

Matching 401(k) Plan

Affordable & Comprehensive Medical, Dental & Vision Plans

Healthcare Flexible Spending Accounts

Parental Coaching

Before and after child birth for all mothers and fathers including adoptive and foster parents

Generous Parental Leave and Support

Paid parental/child bonding and preparation leave with additional support services for all parents.

Meet our leadership

Our leadership team is made up of successful insurance veterans who love tech, and successful tech veterans who love insurance. (Yup, we found 'em.)

Cover Whale Culture

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, welcome aboard.

Career opportunities