Senior Manager, Forward Deployed Engineering

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. ABOUT THE ROLE We're looking for a Senior Manager of Forward Deployed Engineering to build and lead our FDE team. This is a hands-on leadership role for someone who loves engineering, thrives in front of customers, and gets excited about building teams from the ground up. You'll initially lead a team of approximately 5–10 FDEs while staying directly involved in customer engagements. You'll work alongside our engineers to solve complex technical problems, help customers understand what's possible with Sycamore, and turn ambitious ideas into production deployments. We're not looking for someone who wants to manage from the sidelines. We want a leader who can roll up their sleeves, earn the trust of engineers and enterprise customers alike, and help build a world-class FDE organization. WHAT YOU'LL DO - Build and lead the team. Recruit, mentor, and develop exceptional Forward Deployed Engineers. Set a high bar for engineering talent while creating a team that thrives in a fast-moving startup. - Stay hands-on. Work directly with customers and engineers on technical discovery, solution design, implementation, and deployment. Be comfortable jumping into technical problems when needed. - Own customer outcomes. Lead complex enterprise engagements from initial discovery through production deployment, making sure we're solving the right problems and delivering real business value. - Be a technical and commercial partner. Build strong relationships with customer engineering teams and executive stakeholders. Communicate technical concepts clearly, inspire confidence, and help customers see what's possible. - Create the FDE playbook. Establish the processes, tools, and best practices that help us deliver exceptional customer experiences as the team grows. - Partner across Sycamore. Work closely with Engineering, Product, and GTM to bring customer feedback into the product and identify opportunities to improve how we build and deploy. - Help shape the organization. Define what great FDE work looks like at Sycamore and build the foundation for a team that can scale. WHAT WE'RE LOOKING FOR - Experience leading customer-facing engineering, forward-deployed engineering, applied AI, or similar technical teams. - A strong software engineering background with the technical credibility to guide architecture decisions, troubleshoot complex problems, and work alongside engineers. - Experience deploying complex software or AI systems into enterprise environments. - A track record of hiring, mentoring, and developing high-performing engineers. - Strong customer instincts and the ability to build relationships with technical teams and senior executives. - Excellent communication skills and the ability to explain complex technical ideas in a way that gets people excited. - A mix of startup and larger-company experience, with an understanding of how to move quickly without sacrificing quality. - Comfort with ambiguity, changing priorities, and building processes where none exist. BONUS POINTS - Experience building or scaling an FDE organization. - Hands-on experience with LLMs, AI agents, or enterprise AI applications. - Experience with enterprise integrations, APIs, cloud infrastructure, and production deployments. - Experience partnering with sales teams on complex technical opportunities. - Experience taking a customer-facing engineering function from its earliest stages into a repeatable, scalable organization. WHY SYCAMORE You'll have the opportunity to build a critical part of Sycamore from the ground up, work directly with our leadership team, and help some of the world's largest enterprises put AI agents to work. This is a chance to lead, build, and have a direct impact on both our customers and the company we're creating. [https://app.ashbyhq.com/api/images/user-content/c260bb1b-3f03-4953-b376-3a7cfff36d87/e8b1c10d-f726-4271-8ab7-637a5c576034/Screenshot%202026-10-19%20at%2010.29.53%E2%80%AFPM.png]