Commercial Lead, Insurance

About Sycamore

Sycamore is building the trusted agent operating system for the enterprise. Our platform helps companies build, deploy, and orchestrate AI agents that take on real operational work, with the security and control large organizations need. We are a small, engineering-led team working directly with Fortune 500 enterprises. We have raised $65M from Coatue and Lightspeed, along with other investors and industry leaders.

About the role

You will own Sycamore’s commercial results in one industry: finding the right customers, understanding their operations well enough to be useful in a technical conversation, running deals from first meeting through production deployment, and building the account relationships that turn a first workflow into a platform commitment.

This is a technical commercial role at an engineering-led company: you will spend as much time with operators and engineers as with executives, and overselling a capability we do not have costs us far more than a slow quarter. Early customers in a new category do not arrive through a mature pipeline, so the work is original: identifying which companies in your industry are ready, finding the executive who owns the problem and the operator who feels it, and constructing a first engagement narrow enough to succeed and consequential enough to matter.

Insurance at Sycamore

Insurance runs on documents and judgment at scale: submission intake and triage, underwriting review and referral, first notice of loss through claims adjudication, policy servicing and endorsements, subrogation and recovery, appeals, and broker correspondence. Much of it moves through email, PDFs, and legacy policy administration systems that will not be replaced any time soon. The work is well-suited to agents and genuinely hard to automate with anything less. Decisions need to be explainable, consistent, and defensible to regulators and to the policyholder. Carriers need agents that operate inside their authority limits, escalate to a licensed human at the right threshold, and leave a record of why a recommendation was made.

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.

What we are looking for

• 8–15 years of experience in enterprise sales, technical account leadership, or a commercial role with direct revenue ownership. We will make exceptions for exceptional people in either direction.
• 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.

Interview process

• A 30-minute introductory conversation.
• Two 60-minute conversations, one on how you find and develop enterprise opportunities and one on technical discovery for an agent deployment.
• A working session where you present a segment and account plan for a real part of your industry, using the research and judgment you would apply on the job.

Why join

• Own an industry at a company defining a new enterprise category.
• Sell a technical product to technical buyers, alongside engineers who deploy it with you.
• Work on deployments where the outcome is measurable operational change, not a shelf-ware license.
• Shape which problems Sycamore solves next through what you learn in the market.
• Join early enough to build the commercial playbook rather than inherit it.
• Receive competitive cash compensation and meaningful equity in the company you are helping build.