Mid-Market 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 a Mid-Market Account Executive to drive consultative engagements and expand our corporate market share among mid-market and enterprise-track organizations. You own the full cycle in a named territory: sourcing your own pipeline, running discovery with CIOs, CTOs and heads of AI and engineering, and department heads, building the business case, steering security and procurement, and closing six-figure, multi-year platform agreements.

You will sell alongside product leaders, and run many deals in parallel, on cycles of roughly 45 to 90 days. 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 sales cycles end to end. Build pipeline, manage evaluations, negotiate commercial terms and close multi-stakeholder deals at mid-market and growth-stage companies.

• Run a high-velocity book: qualify quickly, carry several evaluations in parallel and keep an accurate forecast.

• Serve as the expert in conversations with CIOs, CTOs and heads of AI and engineering, demonstrating deep understanding of Sycamore's platform and its 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

• 4+ years closing B2B software at mid-market and growth-stage companies, with consistent quota attainment on six-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 running buying processes end to end: security review, legal and procurement, and the discipline to keep them moving without losing momentum.

• 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 executives and with technical teams.

• Comfort with regular travel.

Why join

• Own your book end to end and help build Sycamore’s velocity motion.

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

• Your wins become the playbook.

• Go deep with mid-market leaders modernizing and transforming their business with AI.

• Join early enough to shape how Sycamore moves from pilot to payoff, giving every business user, from operations to finance to the front line, software built around the way they actually work.