Commercial Lead, Retail

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.

Retail at Sycamore

Retail runs a high volume of repetitive operational decisions under thin margins and hard seasonal deadlines: assortment and pricing changes, supplier and purchase-order management, catalog and product-data quality, promotion setup, store and field operations, returns and claims, and customer-service escalation. The work is distributed across merchandising, supply chain, store operations, and care teams that rarely share a system of record.

Retail also moves faster than most enterprise segments. Buyers will run a pilot in weeks rather than quarters, and they will judge it on peak-season readiness and hard operating metrics. That rewards a seller who can scope a first deployment tightly and prove value before the next planning cycle closes.

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 retailers, consumer brands, or e-commerce and supply-chain organizations, with an understanding of how merchandising, supply chain, and store operations buy differently.
• Comfort with retail's operating rhythm: seasonality and peak freeze windows, thin margins, franchise and store-level variation, and integration with POS, ERP, and order-management systems.
• 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.