Commercial Lead, Retail
Palo AltoFull-timePosted 2mo ago
About the role
Own Sycamore’s commercial results in one industry by finding the right customers, understanding their operations, running deals from first meeting through deployment, and building account relationships that turn a first workflow into a platform commitment in a technical, engineering-led environment.
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 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.
- Executive presence and high EQ.
- AI-native: experience using modern AI systems in your work and ability to discuss agent capabilities and limitations from practice.
- Comfort with startup ambiguity, broad ownership, and regular customer travel.
Skills
Required:Pipeline managementTechnical discovery
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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