Strategy & Operations Intern

Sycamore; Palo Alto (CA); On-site; USD 30,000 - 60,000; Full time

Benefits offered by this job

Equity in early-stage company

Competitive compensation

Direct mentorship from founders

Job summary

Sycamore is building the trusted agent operating system for the enterprise. We seek an analytical intern to work directly with the founders and leaders across engineering, commercial, and recruiting operations.

You will own real problems, run planning cycles, and build impactful processes with modern AI tools to accelerate decisions. You will contribute to pricing, reporting, and operational improvements that meaningfully shape deployment outcomes and efficiency.

Qualifications

• Currently pursuing an undergraduate or graduate degree, or recently graduated.
• Strong analytical ability with data-driven problem solving.
• Experience owning an analytical problem and driving to a conclusion.
• Comfort with ambiguity and operational follow-through.

Responsibilities

• Own analytical and operational problems end to end from framing to implementation.
• Run planning cycles, goal setting, and review cadences.
• Design and improve internal processes across finance, recruiting operations, vendor management, and commercial operations.
• Support pricing, deal structuring, and commercial analysis with the go-to-market team.
• Communicate recommendations clearly to founders, engineers, and customers.

Skills

Analytical thinking

Data fluency

SQL querying

AI tooling familiarity

Communication writing

Education

Undergraduate or graduate student

Recent graduate

Tools

SQL

Excel

AI tools

Job description

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 AI agents 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 building the model that decides how we price a deployment, standing up the reporting that tells us whether our deployments are actually succeeding, running the planning cycle that sets company priorities, or fixing 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, forming a recommendation, and being willing to defend it. The rest is operational follow-through, which is where most of the value is and where most people stop.

We are an engineering-led company, and this role is expected to be technical enough to keep up. You should be comfortable querying data yourself, reading enough of a system to understand what it produces, and using modern AI tools to do in an afternoon what would once have taken a week.

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 the work looks like

• Build the pricing and packaging model for enterprise deployments, and pressure-test it against the deals actually in front of us.
• Stand up the reporting that shows how deployments are performing: adoption, expansion, delivery cost, engineering time per customer, and make it something leaders actually use.
• Run a planning cycle end to end: gather inputs, surface the real tradeoffs, drive the decisions, and make sure the outcome is written down and followed.
• Take a broken internal process: candidate scheduling, vendor management, contract flow, expense handling, and rebuild it so it stops consuming attention.
• Analyze where engineering and commercial effort is going, and show leadership where it is not matching stated priorities.
• Build the operating cadence for a function that has outgrown doing it informally.
• Investigate a question nobody has had time to answer, and come back with a recommendation clear enough to act on.

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

Hard problems, real impact

Trust architectures, memory systems, multi-agent coordination. The foundational layer that makes AI agents work in production.

Small team, high ownership

Every engineer shapes the product and the culture. No layers of process between you and the work that matters.

Backed by the best

$65M from Coatue, Lightspeed, Abstract Ventures, Dell Technologies Capital, 8VC, and notable industry angels.

Grow with us

Competitive compensation, meaningful equity, and a genuine focus on your growth as the company scales.