Commercial Lead, Financial Services

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.

Financial services at Sycamore

Financial institutions run enormous volumes of judgment-heavy work: client onboarding and periodic review, credit analysis and memo preparation, loan operations, reconciliation and exception handling, dispute and complaint handling, regulatory reporting, and research synthesis. Most of it is document-heavy, deadline-driven, and already governed by a control framework. That control framework is the opportunity, not the obstacle. These firms will not adopt an agent they cannot explain to a regulator. They need attributable identity, scoped permissions, human approval at the right step, and an audit trail that survives examination. That is what Sycamore is built to provide, and it is why the technically credible seller wins here.

What you will do

• 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 banks, asset managers, insurers, payments companies, or financial-data providers, with a real understanding of how these firms buy.
• Comfort with the control environment around financial services: model risk management, audit and examination, data residency, change control, and third-party risk, as a constraint you can sell within rather than one you route around.
• 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.