Role Description We’re looking for a Senior 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. Qualifications - 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. Requirements - 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. Benefits - Competitive salary & equity - Medical, dental & vision insurance - 401k with company match - Unlimited PTO - Work from home friendly