Strategy & Operations

Work on whatever most needs to be figured out: planning, metrics, pricing, hiring operations, internal systems, and leave each one running better than you found it.

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

Strategy & Operations at Sycamore is a generalist role for someone who is good at reducing messy problems to clear decisions and then making the decision stick. There is no fixed remit. In a given quarter the highest-leverage work might be the model that decides how we price a deployment, the reporting that tells us whether deployments are actually succeeding, the planning cycle that sets company priorities, or an internal process that is quietly costing everyone hours.

You will work directly with the founders and with engineering, commercial, and recruiting leaders. Most of the work is analytical: getting the data, understanding what it says, and forming a recommendation you are willing to defend. The rest is operational follow-through, which is where most of the value is and where most people stop. The scope grows with what you demonstrate.

What you will do

• Own analytical and operational problems end to end, from framing through recommendation through implementation.
• Run company planning, goal setting, and the review cadence that keeps them honest.
• Design and improve internal processes and systems across finance, recruiting operations, vendor management, and commercial operations.
• Support pricing, deal structuring, and commercial analysis alongside the go-to-market team.
• Find the work nobody owns yet, take it on, and hand it off well once it is systematized.
• Write clearly for an audience of founders, engineers, and customers.

What we are looking for

• 4-10 years of experience in strategy, operations, consulting, banking, product operations, or a generalist role at a high-growth company. We will make exceptions for exceptional people in either direction.
• Strong analytical ability. You can build a model, query data directly, and tell the difference between a real signal and an artifact of how the data was collected.
• Evidence of operational follow-through. You have implemented recommendations, not only produced them.
• Comfort with ambiguity and no established playbook. Much of this role is deciding what deserves attention.
• Clear writing. Your recommendations should be understandable to someone who was not in the room.
• Technical fluency. You do not need to be an engineer, but you should be able to work with data yourself and understand what our product does at more than a surface level.
• AI-native. You use modern AI systems and agents to expand your own throughput, while owning the judgment and the conclusions.
• High integrity with numbers. You would rather present an uncomfortable finding than a flattering one.

Interview process

1. A 30-minute introductory conversation.
2. Two 60-minute conversations, one on analytical problem solving and one on operational judgment.
3. A working session where you take a real, open Sycamore problem, do the analysis, and present a recommendation you would be willing to own.

Why join

• Work directly with the founders on the decisions that shape the company.
• Take on genuinely varied problems rather than one narrow function.
• Build the operating foundation of a company early enough that it compounds.
• Work alongside engineers building something technically hard, in a company where operations is expected to keep up.
• Receive competitive cash compensation and meaningful equity in the company you are helping build.