Strategy & Operations Intern

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. As an intern you will own a real problem, not a shadow project. The scope will be narrower than a full-time remit and you will have a direct partner on the team, but the work is expected to ship and be used after you leave. We will pick something consequential enough that finishing it matters. 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 - Currently pursuing an undergraduate or graduate degree, or recently graduated. We care about how you think, not your year or program. - Prior internship, research, or project experience where you owned an analytical problem and saw it through to a conclusion. - 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 - Own a real problem with a real outcome, not a summer exercise. - Work directly with the founders and with engineering and commercial leaders. - See how an early-stage enterprise company actually makes decisions. - Build judgment quickly in an environment where the feedback loop is short. - Receive competitive cash compensation and meaningful equity in the company you are helping build. [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]