Deployment Strategist

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

Own the business outcome of every Sycamore deployment: scope it before it sells, run the engagement, prove what it returned, and build the case for what the customer should automate next.

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.

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.

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.

• 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…