Senior Manager, Forward Deployed Engineering
Posted 11 days ago
The role in short
Lead and build a team of Forward Deployed Engineers who embed with Fortune 500 customers to design, implement, and deploy production AI agent solutions.
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.
Prep for this interview
4 questions likely to come up at Sycamore, each matched to a line in this posting.
- 1Integrations and APIs
They wrote: “Experience with enterprise integrations, APIs, cloud infrastructure, and production deployments.”
Walk me through connecting our product to a customer's internal system that has no documentation.
How to answer
Why they ask: This happens weekly in the job. They want a calm, step-by-step method.
- Find who owns the system and get read access to a test environment
- Watch real traffic or logs to learn the data shapes
- Build a thin adapter with logging around every call
- Agree on how failures get reported, and who fixes what
Tip: Talk about finding the owner of the system first. The code is the easy part.
- 2LLMs, RAG and agents
They wrote: “Hands-on experience with LLMs, AI agents, or enterprise AI applications.”
When would you use an agent that takes actions, and how do you keep it safe?
How to answer
Why they ask: Agent work is growing fast in FDE postings. Senior candidates are expected to know where agents fail.
- Use agents for multi-step tasks with clear success checks; avoid them where one wrong action is costly
- Give the agent narrow tools and permissions, not broad access
- Require human approval for risky actions
- Log every step so the customer can audit it
Tip: Start from the cost of a wrong action. Limit what the agent can do, and log everything.
- 3Discovery and scoping
They wrote: “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.”
A customer says “we want AI in our claims process.” What do you ask in the first meeting?
How to answer
Why they ask: Most FDE work starts this vague. They want to hear you find the real problem before you pick a tool.
- Map the current process: who touches a claim, in what order, with which systems
- Find the slowest or most error-prone step and ask what it costs them
- Agree on one measurable goal (for example time per claim, or error rate)
- Ask what data you can access, and who signs off on security
Tip: Ask about the work, not the technology. Who does it today, how long it takes, what a mistake costs, and how they'd know it got better.
- 4Ownership and working with customers
They wrote: “Comfort with ambiguity, changing priorities, and building processes where none exist.”
Tell me about a project where the requirements kept changing. What did you do?
How to answer
Why they ask: Ambiguity is the norm. They want proof you can keep moving without a clear spec.
- The project and why requirements kept moving
- What you did to pin them down (short demos, written decisions)
- The trade-offs you made to keep shipping
- The result, with a number if you have one
Tip: Show how you reduced the change, beyond how you coped with it.
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