Enterprise Commercial Lead, AI-Driven Insurance Tech

Sycamore Labs, Inc.; Palo Alto (CA); Hybrid; USD 180,000 - 300,000; Full time

Job summary

Sycamore Labs, Inc. is seeking a technical commercial leader in Palo Alto to own enterprise sales, driving the full cycle from first contact to production deployment and platform adoption.

You will collaborate closely with operators and engineers, balancing technical credibility with business outcomes to turn early engagements into durable revenue. The role blends sales and technical conversations, requiring deep industry knowledge of insurance operations, security reviews, and enterprise buying

Qualifications

• 8-15 years of experience in enterprise sales, technical account leadership, or a commercial role with direct revenue ownership.

Responsibilities

• Own pipeline, forecast, and revenue for your industry from first contact through deployment, adoption, and expansion.
• Run technical discovery with engineers, turning broad AI goals into a concrete workflow with measurable outcomes.
• Navigate enterprise buying: security, procurement, legal, data protection, and internal approvals for pilots to become contracts.
• Stay accountable after signature for adoption, measurable value, executive communication, and renewal or expansion.
• Build references, deployment patterns, and segment knowledge to accelerate future deals.

Skills

Enterprise sales

Technical leadership

Revenue ownership

Executive presence

AI-native

Job description

Sycamore Labs, Inc. is seeking a technical commercial leader in Palo Alto to own enterprise sales, driving the full cycle from first contact to production deployment and platform adoption.

You will collaborate closely with operators and engineers, balancing technical credibility with business outcomes to turn early engagements into durable revenue. The role blends sales and technical conversations, requiring deep industry knowledge of insurance operations, security reviews, and enterprise buying