Domain Expert, Insurance

Bring deep insurance expertise into the room where enterprise agents get designed, and turn it into specifications engineers can build the same week.

About Sycamore

Sycamore is building the trusted agent operating system for the enterprise. Our platform helps companies build, deploy, and orchestrate agentic apps 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.

The role

The hardest part of deploying an agent into an enterprise workflow is almost never the model. It is knowing what the workflow actually is: who decides what, under whose authority, against which rules, with what evidence, and what happens when the answer is wrong. That knowledge lives in people who have done the work, and you are one of them.

You will pair directly with our Applied AI engineers on customer deployments. They build; you supply the substance that makes what they build correct. Your output is not advice or a slide. It is a specification precise enough to become a workflow definition, a rule set, a review screen, and a set of thresholds, followed by the judgment of whether what came back is actually right, which is a different question from whether it runs. You will be in front of customers throughout.

Insurance at Sycamore

Insurance runs on documents and judgment at scale, and the volumes are enormous. Submission intake and triage. Underwriting review and referral. First notice of loss through adjudication and settlement. Policy servicing and endorsements. Subrogation and recovery. Complaints and regulatory inquiries.

Much of this moves through email, PDFs, and policy administration systems that will not be replaced. The decisions need to be consistent, explainable, and defensible, to a regulator, to a reinsurer, and to the policyholder.

That makes it an unusually good fit for our platform and an unusually bad fit for anything that cannot show its work. Agents need to operate inside authority limits, escalate to a licensed human at the right threshold, and record why a recommendation was made.

What you will do

• Serve as the domain authority on customer deployments in your industry, from discovery through production.
• Translate real operational processes into specifications precise enough to build from: decision points, roles and authority, rules, thresholds, escalation, and evidence requirements.
• Build trust with customer operators, executives, and control functions as someone who has done their job.
• Feed patterns back to Product and Core AI so that what we learn in one deployment becomes a platform capability rather than a repeated conversation.
• Help our commercial team evaluate which opportunities in your industry are real and which are not.

What we are looking for

• 10+ years in insurance, in a role where you owned or governed the actual process: claims, underwriting, policy operations, compliance, or product.
• Deep familiarity with the operating model: authority limits and referral thresholds, fair claims handling standards, state-by-state regulatory variation, and the legacy policy administration estate.
• Direct experience with the operational reality of at least one of: claims handling, underwriting and submission triage, policy servicing, or regulatory complaint handling.
• The ability to write a process down precisely, clearly enough that an engineer can build from your account of a workflow’s decision points, authority limits, and exception paths.
• Judgment about automation. You know which parts of your domain are genuinely rule-based, which require expertise, and which should never be delegated to software at all.
• Executive presence and high EQ. You can be the credible voice with a customer’s operators and their leadership in the same conversation.
• Intellectual honesty. You will sometimes need to tell us that something we built is wrong, or that a customer’s request is a bad idea.
• AI-native. You use modern AI systems in your own work and can reason about where they help and where they mislead.
• Comfort with startup ambiguity, broad ownership, and regular customer travel.

You do not need to be technical in the software sense. You do need to be precise, and you need to be genuinely curious about how the system works.

Interview process

1. A 30-minute introductory conversation.
2. Two 60-minute conversations, one on the operational depth of your domain and one on how you would specify a workflow for a build team.
3. A working session where you take a real process from your industry, specify it end to end, and defend the decisions you made about authority, thresholds, and what should not be automated.

Why join

• Put deep domain expertise directly into production software rather than into recommendations.
• Work alongside engineers who will build what you specify, in the same week.
• Define how agents handle consequential work in an industry you know well.
• Sit at the front of a category that is still being defined, with real influence over what gets built.
• Join early enough to shape how Sycamore approaches your industry.
• Receive competitive cash compensation and meaningful equity in the company you are helping build.