Nirvana Insurance - Senior Fleet Underwriter
Requirements
• 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. • 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.
Responsibilities
• 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.
Benefits
• 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. • 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.
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