Commercial Lead, Insurance
Hybrid (Palo Alto)Full-timePosted 2mo ago
About the role
Own an industry at Sycamore: drive commercial results, understand customer operations, and shepherd deals from first meeting through production deployment and expansion in the Insurance domain.
Responsibilities
- Own pipeline, forecast, and revenue for your industry, from first contact through production deployment, adoption, and expansion.
- Run technical discovery alongside our engineers, reducing a broad AI ambition to a specific workflow with real users, permissions, risks, and measurable outcomes.
- Navigate enterprise buying: security review, procurement, legal, data protection, and the internal approvals that decide whether a pilot becomes a contract.
- Stay accountable after signature for adoption, measured value, executive communication, and renewal or expansion.
- Build the references, repeatable deployment patterns, and segment knowledge that make the next deal in your industry faster than the last.
Qualifications
- 8-15 years of experience in enterprise sales, technical account leadership, or a commercial role with direct revenue ownership.
- Experience selling technical software into carriers, brokers, MGAs, or reinsurers, with a real understanding of how insurance organizations buy and pilot.
- Working knowledge of the insurance operating model: underwriting authority, claims handling standards, state-by-state regulatory variation, and the legacy policy administration estate, as a constraint you can sell within.
- The technical credibility to hold a substantive conversation with engineers and security teams without needing an engineer in the room for every exchange.
- Evidence of early-stage commercial work: opening a segment, landing first customers for a product without an established category, or building a territory from very little.
- Strong discovery instincts. You can tell the difference between an interesting conversation and a real problem with a budget owner and a path to production.
- Executive presence and high EQ. You can earn trust with a COO, a head of operations, a CISO, and a staff engineer in the same week.
- AI-native. You use modern AI systems in your own work, and you can speak about agent capabilities and limitations from direct experience rather than from a deck.
- Comfort with startup ambiguity, broad ownership, and regular customer travel.
Skills
Required:Enterprise salesTechnical discoveryNegotiation and deal craftExecutive communication
Benefits
- Competitive cash compensation and meaningful equity in the company you are helping build.
Last updated Oct 22, 2026. Interested? Apply on the company site.
About Sycamore
The Trusted Agent Operating System
Sycamore: The trusted agent operating system for the enterprise.
Progressive Trust SystemAdaptive System GenerationContinuous ImprovementCollective IntelligenceTrust by designSecureCompliantAuditable
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