SENIOR UNDERWRITER WHO WE ARE 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. ABOUT THE ROLE We’re looking for a Senior Fleet Underwriter who embodies what next-generation underwriting looks like at Nirvana: less time processing files, more time making decisions, building relationships, and closing business. As our AI platform absorbs the initial exposure validation, pricing prep, and file review, you’ll step in where it matters most—making the call, leading the negotiation, and owning the broker relationship. You’ll also play an active role in making our models smarter, surfacing what the AI misses and feeding that context back to our Product team. This is a high-visibility role at the intersection of technical expertise, market relationships, and executive presence. WHAT YOU’LL DO * Review AI-generated submission analyses, pricing outputs, and exposure summaries—treating every output as a first draft and identifying what the model missed before making a decision. * Make fast, precise underwriting decisions on commercial trucking accounts, knowing when to approve, modify, decline, or escalate. * Catch inconsistencies in submission data that AI may miss: contradictions across operation class, mileage, commodity, FMCSA safety scores, DOT history, and loss run patterns. * Read and explain all pricing components—tier, experience mod, territory factor, schedule mod—and build a rate rationale you can walk a broker through without reconstructing the math. * Track carrier appetite, competitive positioning, and where Nirvana wins and where it doesn’t; when a broker asks “where does this land?” you answer from experience, not a guess. * Build and deepen broker relationships proactively. Be the underwriter brokers call with their best accounts because they trust you to respond quickly, price fairly, and not waste their time. * Lead deal negotiations with a clear floor, a story, and a position. Understand the broker’s situation and competitive set—know when to move and when to hold. * Present coverage, pricing, and Nirvana’s value proposition to insured leadership teams—including CFOs and fleet managers—with confidence and clarity on large accounts. * Document model blind spots with specific account-tied context and share structured feedback with Product to improve AI accuracy over time. This is part of the job, not optional. * Mentor junior underwriters on risk identification, pricing fluency, broker engagement, and how to work effectively alongside AI tools. WHAT YOU BRING Must-Haves * 5+ years of commercial trucking underwriting experience with a track record of writing profitable business. Experience with 50+ units risks, liability deductible retention structures, and reporting policies a plus. * Deep technical knowledge of trucking operations, classes of business, FMCSA/DOT data, commodity risk, and loss run analysis—you catch what the model misses. * Pricing fluency across all components: tier, experience mod, territory factor, schedule mod. You know when a number is right, when it’s defensible, and when it’s wrong. * Demonstrated ability to build trusted broker relationships and win competitive accounts—brokers bring you their best business because you’ve earned it. * Comfort with deal negotiation. You go in with a floor, a story, and a position. You know the difference between being agreeable and closing. * Executive presence: you can present coverage and pricing to a CFO or fleet director, absorb hard questions, and make the insured feel confident before they sign. * Collaborative mindset and genuine interest in working alongside AI tools—and actively improving them through structured feedback. Nice-to-Haves * Experience working with telematics, IoT data, or AI-assisted underwriting platforms. * Background mentoring or developing junior underwriters. * Experience at a high-growth insurtech or technology-forward carrier. * Formal negotiation training or structured deal-coaching experience. WHY JOIN NIRVANA * Transform a legacy industry. Help define what next-generation underwriting looks like in a data-driven insurance company. * Real ownership. Shape underwriting decisions that will scale across the business. * High-impact environment. Work closely with leadership and cross-functional teams to drive meaningful change. * Accelerated growth. Join a company growing rapidly with strong product momentum and backing from top-tier investors. BENEFITS * Competitive salary & equity * Medical, dental & vision insurance * 401k with company match * Unlimited PTO * Work from home friendly We set our salary ranges using compensation data from companies similar to our stage and size For this role, the estimated salary range for this position is $140,000 - $200,000. 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.