Deployment Strategist

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 own the business result of a customer engagement from the first conversation with the customer through to the expansion that follows. Our Applied AI engineers own the technical result: the workflow runs, the agent behaves, the integration holds under production load. You own everything around it. The engagement lands in scope and on the date, the value it created is measured in numbers the customer already trusts, and their leadership knows what to build next. You work as a pair with the engineer on every deployment, and with the account executive on everything above it. You program manage the work day to day, you build the map of the customer’s organization, and you are the person who says a use case is too large for a first release or that a go-live date does not survive the resourcing behind it. That is unpopular work, and it is most of what protects a deployment. You do not carry a quota. You are expected to know the heartbeat of the account better than anyone else at Sycamore. WHY THIS ROLE EXISTS A pilot that works technically and then dies quietly is the most common failure in enterprise AI. The agent runs, the demo goes well, and nine months later nobody can say what changed in the operating numbers, so the renewal conversation restarts from zero. Our engineers deploy fast, and that speed creates a second job. Someone has to agree what success means before the build starts, keep the first release small enough to reach production, measure the result the way the customer’s own finance and operations teams measure things, and turn one working workflow into the next five. That is this role. WHAT YOU WILL DO - Work the opportunity with the account executive before it closes: discovery, process walkthroughs, and a first release you would be willing to put your own name on. - Write the success criteria into the agreement: what gets measured, against what baseline, by when, and who on the customer’s side signs that it happened. - Program manage pilots and full implementations end to end: scope, resourcing, dependencies, milestones, go-live dates, and the weekly rhythm that keeps all of it honest. - Agree the business case before the build starts. Set the baseline, the metric, and the measurement method with the customer in writing, while there is still time to instrument it. - Measure and publish the outcome in the customer’s own terms: hours returned, cycle time, exception rates, cost per case, whatever their operating reviews already track. - Hold scope against pressure from both sides, and protect the engineer’s ability to ship something that works. - Build and maintain the account map with the account executive: processes, owners, budget holders, adjacent teams, and the politics between them. - Produce the ranked list of use cases and product capabilities the customer should take on next, each one sized, sponsored, and tied to a business owner. - Make the call on what should not be automated at all, and be able to defend it to the customer’s sponsor and to our engineers. - Bring a point of view to roadmap conversations. When the same need shows up across three accounts, make the case that it belongs in the product roadmap. - Hand expansion to the account executive with the evidence already assembled, and stay in the room for that conversation. - Feed the field back into product: which use cases repeat across customers, where measurement is hard, and what keeps deployments from reaching production. WHAT THIS ROLE IS NOT - It is not a customer success role that begins at go-live and reports on adoption. - It is not project management without a point of view on what should be built. - It is not a quota-carrying sales role. You do not own the number, though you own most of what makes the number possible. WHAT WE ARE LOOKING FOR - 6+ years in enterprise program delivery, consulting, value engineering, customer success leadership, or a deployment role at an enterprise software company. We will make exceptions for exceptional people in either direction. - Evidence you have carried complex enterprise implementations all the way to production, with real dates, real dependencies, and real internal resistance. - You have been in the room before a deal closed and shaped what got signed, not only what got built. - Product judgment. You can take a messy operational process and decide what an agent should own, what it should hand back, and what should stay human, then hold that line under pressure from both the customer and our own engineers. - The ability to build a value case an enterprise finance team will accept: a defensible baseline, an honest attribution argument, and numbers the customer can reproduce from their own systems. - Operational literacy. You can sit with a head of shared services or an operations lead, follow the process they describe, and find the steps where the cost actually sits. - The willingness to be the person who says no to scope, and the judgment to know when saying yes is the right call. - Enough technical depth to be useful next to an engineer. You understand what an agent can and cannot do, what an integration costs, and why a permission model matters. - Executive presence. You can brief a COO on outcomes in the morning and spend the afternoon in a process walkthrough with the team that does the work. - Commercial instinct without a quota. You can see where an account expands next and set it up for the account executive rather than closing it yourself. - AI-native. You use modern AI systems in your own work, and you can speak about agent capabilities and limitations from direct experience. - Comfort with startup ambiguity, broad ownership, and regular customer travel. INTERVIEW PROCESS 1. A 30-minute introductory conversation. 2. One 60-minute conversation on an enterprise implementation you ran to production, identifying and defending the business value the customer expected and received. 3. A working session where you take a real deployment scenario and present the engagement plan: scope, milestones, measurement approach, risks, and the expansion path that follows. WHY JOIN - Own the business outcome of deployments at a company defining a new enterprise category. - Work as a pair with engineers who ship, on deployments that reach production in weeks. - Prove value with real operating numbers instead of an adoption dashboard. - Shape which use cases Sycamore builds next through what you see in the field. - Join early enough to build the deployment playbook rather than inherit it. - 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]