Strategy & Operations

Sycamore Labs, Inc.; Palo Alto (CA); On-site; USD 180,000 - 280,000; Full time

Benefits offered by this job

Competitive cash compensation

Meaningful equity

Growth opportunities

Job summary

Sycamore Labs, Inc. in Palo Alto is seeking a Strategy & Operations generalist who can translate messy problems into clear decisions and drive impact across pricing, planning, and internal systems.

You will work directly with the founders and with engineering, commercial, and recruiting leaders. Most work is analytical—gathering data, interpreting it, and presenting defensible recommendations—followed by hands-on implementation.

Qualifications

• Strong analytical ability with data-driven decision making.
• Evidence of delivering implemented recommendations.
• Comfort with ambiguity and building new playbooks.

Responsibilities

• Own analytical and operational problems end to end, from framing to recommendation to implementation.
• Run planning, goal setting, and review cadence across the company.
• Design and improve internal processes in finance, recruiting operations, vendor management, and commercial operations.
• Support pricing, deal structuring, and commercial analysis with the go-to-market team.
• Take on unowned work and systematize it for scale.
• Write clearly for founders, engineers, and customers.

Skills

Analytical ability

Operational follow-through

Clear writing

AI-native

Technical fluency with data

Job description

Go-to-Market & Operations · Palo Alto · full-time

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.
• 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.
• 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.

Hard problems, real impact

Trust architectures, memory systems, multi-agent coordination. The foundational layer that makes agentic apps 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.