Enterprise Account Executive

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

Sycamore is hiring an Enterprise Account Executive to open and expand Sycamore’s largest strategic accounts, selling transformational outcomes to CIOs and business leaders at Fortune 1000 companies. You own the full cycle in a named territory: sourcing your own pipeline, running discovery with CIOs, Chief AI Officers and leaders of AI platforms, building the business case, steering security and procurement, and closing six- and seven-figure platform agreements.

You will sell alongside the CEO and product leaders. Our best conversations start from a specific business problem and end with a working application the customer's team can see running, not a platform tour. You will partner with our forward deployed engineers and deployment strategists, who build that application during the sale. The role suits someone who wants to shape how an early company sells.

What you will do

• Lead enterprise sales cycles end to end. Build pipeline, manage evaluations, negotiate commercial terms and close multi-stakeholder deals at Fortune 1000 companies and high-growth enterprises.

• Serve as the expert in conversations with CIOs, Chief AI Officers and leaders of AI platforms, demonstrating deep understanding of Sycamore's platform and its enterprise value proposition. Lead discovery that lands on a specific, high-value business problem, and frame the platform against that problem rather than against a feature list.

• Build the business case (the problem, the value and the return) and shape the deal: deployment path (customer cloud or Sycamore-managed) and multi-year agreements with room to expand.

• Guide customers through the technical evaluation and the deployment plan.

• Work closely with marketing to refine our sales strategy and materials based on what you hear in the market, contributing directly to Sycamore's growth.

• Bring what you learn back to the founder and product: ICP refinements, objections, competitive signals and product gaps.

What we are looking for

• 8+ years closing enterprise B2B software at Fortune 1000 companies and high-growth enterprises, with consistent quota attainment on six- and seven-figure, multi-year deals, ideally selling a platform rather than a point tool. We will make exceptions for exceptional people in either direction.

• Exceptional technical aptitude, capable of quickly learning new technologies and articulating complex solutions in a straightforward manner.

• Experience with enterprise buying processes end to end: security reviews, architecture reviews, legal and procurement, and the rigor and patience to work through them without losing momentum. The depth these cycles demand is non-trivial, and you have done it before.

• Comfort in an early, founder-led environment where the product's shape and surface area change rapidly, with the tolerance for ambiguity and the intellectual curiosity to keep learning what the platform can do.

• Clear, concise communicator and strong listener, equally effective with the C-suite and with technical teams.

• Comfort with regular travel.

Why join

• Own a named list of Fortune 1000 accounts and land the lighthouse deals that define Sycamore’s enterprise business.

• Sell side by side with the founder, with a product team that turns your customer feedback into shipped features in days.

• Your wins become the playbook.

• Go deep on agentic AI with the CIOs and business leaders modernizing the world’s largest companies.

• Join early enough to shape how the Fortune 1000 builds software in the AI era.