Senior Fleet Underwriter

About the role

We're seeking a Senior Fleet Underwriter who embodies the future of underwriting at Nirvana. With a focus on making quick, precise decisions, building strong relationships, and closing deals, you'll leverage our AI platform to handle initial exposure validation, pricing preparation, and file review. Your role involves reviewing AI-generated submissions, making informed decisions, negotiating deals, and mentoring junior underwriters.

Responsibilities

• Review AI-generated submission analyses, pricing outputs, and exposure summaries, identifying blind spots and making informed decisions.
• Make fast, precise underwriting decisions on commercial trucking accounts, knowing when to approve, modify, decline, or escalate.
• Build and deepen broker relationships by responding quickly, pricing fairly, and demonstrating expertise in large accounts.
• Lead deal negotiations with a clear floor, story, and position, understanding the broker's situation and competitive set.
• Present coverage, pricing, and Nirvana's value proposition to insured leadership teams with confidence and clarity.
• Document model blind spots with specific account-tied context and provide structured feedback to improve AI accuracy.
• Mentor junior underwriters on risk identification, pricing fluency, broker engagement, and working effectively alongside AI tools.

Requirements

• 5+ years of commercial trucking underwriting experience with a track record of profitable business.
• Experience with 50+ unit risks, liability deductible retention structures, and reporting policies.
• Deep technical knowledge of trucking operations, classes of business, FMCSA/DOT data, commodity risk, and loss run analysis.
• Pricing fluency across all components: tier, experience mod, territory factor, schedule mod.
• Demonstrated ability to build trusted broker relationships and win competitive accounts.
• Comfort with deal negotiation and executive presence.
• A collaborative mindset and genuine interest in working alongside AI tools.

Qualifications

• Must-have: 5+ years of commercial trucking underwriting experience with a track record of profitable business.
• Must-have: Deep technical knowledge of trucking operations, classes of business, FMCSA/DOT data, commodity risk, and loss run analysis.
• Must-have: Demonstrated ability to build trusted broker relationships and win competitive accounts.
• Must-have: Comfort with deal negotiation and executive presence.
• Must-have: A collaborative mindset and genuine interest in working alongside AI tools.

Skills

• Strong analytical and problem-solving skills.
• Excellent communication and negotiation skills.
• Ability to work independently and manage multiple tasks simultaneously.
• Knowledge of telematics, IoT data, and AI-assisted underwriting platforms.
• Experience mentoring or developing junior underwriters.

Benefits

• Competitive salary and equity.
• Medical, dental, and vision insurance.
• 401(k) with company match.
• Unlimited PTO.
• Parental leave.
• Wellness reimbursement.
• Work-from-home friendly policy.

Pay

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.

Schedule

Nirvana offers flexible work arrangements to accommodate your needs.