Member of Product Staff

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 You sit with a handful of customers in one industry and own the product loop: learn how the work runs, turn messy asks into clear product, ship working apps yourself, and decide what should become reusable for every customer in that industry. You focus on one of three industries: financial services, telecommunications, or data centers. You map the workflows that matter, build the first version in Sycamore Forge with AI coding tools, put it in front of real users, and iterate until it sticks. When the same pattern shows up across accounts, you productize it for the core. You work with Applied AI engineers, Deployment Strategists, and the account team. Engineers own deep technical delivery. Strategists own the engagement, success criteria, and business outcome. You own customer signal in, shipped product out, and what should live on the platform. WHY THIS ROLE EXISTS Enterprise AI fails when customer feedback stays in notes and never becomes software people use. Someone has to sit close enough to see the real workflow, ship something that works, and decide what is one-off versus what belongs on the roadmap. That is this role. WHAT YOU WILL DO - Sit with operators and leaders in your industry (often with a Deployment Strategist). Learn how the work runs and what “good” looks like for the product. - Turn ambiguous requests into clear product: who it is for, what first version to build, and what not to build. - Ship working apps and agents in Sycamore Forge in days, not quarters. Put them in front of real users and iterate weekly or faster. - Connect apps to the systems customers already trust, within their permissions. - Iterate with users until the workflow sticks. Deployment Strategists own go-live dates, resourcing, and the commercial engagement. - Separate account-specific work from reusable industry product, and write that up so Engineering can put it on the platform. - Keep a simple industry product backlog, using accounts as evidence, not as engagements you own. - Demo what you built to customer executives. - Track product usage and whether the workflow changed. Deal success criteria and the business case belong to the Deployment Strategist. WHAT THIS ROLE IS NOT - Not a Deployment Strategist role. Strategists own the AE engagement, success criteria in the agreement, pilot program management, the account map, and the business outcome. You own the product and what becomes reusable across the industry. - Not owning one account’s expansion list. You use accounts to learn; you own the industry product backlog. - Not a Domain Expert who writes specs for someone else. You build. - Not a roadmap PM who only writes tickets. You ship working software yourself. - Not pre-sales that stops at the demo. - Not customer success that collects feedback without turning it into product. WHAT WE ARE LOOKING FOR - 3+ years in product management, or equivalent as a founder, early employee, solutions engineer, or forward deployed engineer who moved into product. - Industry experience in financial services, telecommunications, or data centers (see tracks below). - Evidence you have shipped working software yourself: links, repos, demos, or tools people used. - Strong discovery habits. You talk to customers constantly and turn what you hear into product priorities. - AI-native. You use Claude Code, Cursor, Codex, or similar daily, and can go from a customer call to a working prototype in a day or two. - Technical enough to ship in Sycamore Forge yourself and to spot where agents break: bad permissions, weak integrations, or outputs you would not trust in production. - Product judgment. You choose a useful first version and hold scope when a request would break the outcome. - Comfortable with enterprise customers: discovery, pushback, and briefing operators and executives. - Clear writing. You turn a messy conversation into a crisp problem and a first version worth building. - Comfort with startup ambiguity, broad ownership, and regular customer travel. NICE TO HAVE - LLM apps in production: prompts, tool use, MCP, evaluations. - Experience building for regulated or security-conscious enterprises. INDUSTRY TRACKS Financial services. Banks, capital markets, lenders, and fintechs. You might build for onboarding and review, alert triage, credit memos, or operations exception queues, plus governance workflows a firm can explain to a regulator. Helpful: time in or building for financial services; controls, audit, and model risk. Telecommunications and communications. Carriers, cloud communications, network and service assurance, and media. You might build for order-to-activation, network incident and ticket triage, customer care and billing disputes, or partner operations. Helpful: OSS/BSS, network ops, or telecom CX. Data centers. Owners, developers, and operators building capacity with small central teams and many partners. You might build for site readiness (land, power, permits, interconnection), procurement and long-lead equipment, construction milestones, and commitments to boards, lenders, and partners. Focus is the business of the data center company, not building control systems. Helpful: data center development, construction, energy, infrastructure investing, or GPU cloud ops. INTERVIEW PROCESS 1. A 30-minute introductory conversation. 2. A 30-minute culture fit interview. 3. A take-home app building assignment with a 30-minute presentation. 4. A 30-minute systems design interview. WHY JOIN - Build product directly from Fortune 500 customer feedback, not from someone else’s backlog. - Ship on Forge with Applied AI engineers and see your work in production in weeks. - Shape the platform through patterns you find in the field. - Join early enough to define how Product works at Sycamore. - Competitive cash compensation and meaningful equity. [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]