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Underwriting Manager - Fleet

February 27, 2026

This a Full Remote job, the offer is available from: Anywhere

About Nirvana

Nirvana is on a mission to harness the power of data to revolutionize commercial insurance and enable a safer world. We are bringing much-needed innovation into the legacy, trillion-dollar commercial insurance industry. We have developed cutting-edge predictive models that use real-time IoT data from billions of connected devices, allowing us to better understand and price risk. Our AI-driven platform fundamentally changes the way an insurance company operates with personalized risk scoring, faster underwriting, modernized claims, and proactive, data-driven insights to help customers prevent accidents.

We’ve already proven the scale—serving thousands of fleets and more than doubling our written premiums year over year. Our data moat is growing exponentially with more than 30 billion miles of telematics data, leading to more predictive models and new insights into how we can better understand and reduce risk. Altogether, our loss ratio, efficiency, and customer experience are redefining what can be done in the industry.

With $270+ million raised, including our Series D round in December 2025, we’re only accelerating our growth, with strong support from top-tier VCs including Lightspeed, General Catalyst, and Valor. Nirvana’s leadership team has previously helped scale multi-billion-dollar companies from scratch, including Samsara, Rubrik, and Flexport, and includes industry veterans from Hiscox, The Hartford, and RLI.

Why this role matters

As an Underwriting Manager on Nirvana’s Fleet team, you’ll play a critical role in scaling a modern underwriting organization in one of the most complex and high-impact segments of commercial insurance. You’ll lead experienced underwriters, shape underwriting strategy, and help ensure Nirvana grows profitably while transforming how fleet risk is assessed and managed.

This is a high-ownership leadership role for someone excited to build, coach, and operate in a fast-moving environment where underwriting decisions directly influence product, growth, and customer outcomes.

About the role

In this role, you’ll lead and develop a team of underwriters focused on commercial transportation risks, with a strong emphasis on trucking. You’ll partner closely with Business Development, Product, and senior leadership to align underwriting execution with company growth goals. You’ll also help evolve underwriting workflows, authority structures, and referral strategies as Nirvana continues to scale.

Nirvana is a globally distributed company. This role is remote-friendly, with a preference for candidates based in the Eastern or Central time zones.

What you’ll do

Lead, coach, and develop a high-performing team of 4–6 experienced Fleet Underwriters
Drive underwriting execution that balances growth, profitability, and risk discipline
Partner with Business Development to support monthly, quarterly, and annual production goals
Serve as a key point of contact for agents, brokers, and external partners
Own team workflows, including referrals, authority levels, and underwriting standards
Collaborate with senior leadership on underwriting strategy, process improvements, and long-term innovation
Foster a culture of accountability, thoughtful decision-making, and continuous learning

What you bring

Must-haves

Deep experience underwriting commercial transportation risks, ideally within trucking
Demonstrated success leading, coaching, or managing underwriting teams
Strong underwriting judgment and comfort making decisions in dynamic environments
Clear, confident communication skills with internal and external stakeholders
Ability to set goals, prioritize work, and drive outcomes through others

Nice-to-haves

Experience managing or collaborating with distributed or remote teams
Exposure to high-growth or startup environments
Interest in technology-enabled underwriting or data-driven risk models

We set our salary ranges using compensation data from companies similar to our stage and size For this role, the estimated base salary range for this position is $123,000 - $154,000 + 25% variable. The actual base salary will vary depending on multiple factors unique to each candidate, including location, job-related knowledge, transferable skills, work experience and our assessment of your level during the interview process. Nirvana offers equity for all full-time employees, which is not included in the range listed above and will have an impact on your overall compensation.

Nirvana offers a wide range of best-in-class, comprehensive benefits including 100% employer paid healthcare plans, an up to 4% 401k match program, paid time off, parental leave, wellness reimbursement, work-from-home stipend and more.Nirvana is committed to building a diverse and inclusive workforce. If you’re interested in this role, but do not meet 100% of the qualifications listed above, we encourage you to apply. We'd like to consider you for this position and roles that may be a fit in the future.

Nirvana is an Equal Opportunity Employer and considers applicants for employment without regard to race, color, religion, sex, orientation, national origin, age, disability, genetics or any other basis forbidden under federal, state, or local law. Nirvana considers all qualified applicants in accordance with the San Francisco Fair Chance Ordinance.

#LI-Remote

This offer from "Nirvana Insurance" has been enriched by Jobgether.com and got a 82% flex score.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

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