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Deployment Strategist

Sycamore· Go-to-Market & Operations
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Hybrid (Palo Alto)Full-timePosted 1mo ago

About the role

Own the business outcome of every Sycamore deployment from scope through expansion, coordinating with engineers and account executives to define success, manage pilots, measure results, and drive next steps.

Responsibilities

  • 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.

Qualifications

  • 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.

Skills

Required:Enterprise program deliveryValue case developmentExecutive communicationAI-native mindset

Benefits

  • Competitive cash compensation
  • meaningful equity
  • growth-focused environment
  • Hard problems, real impact
  • Small team, high ownership
  • Backed by $65M in funding
Last updated Oct 22, 2026. Interested? Apply on the company site.
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About Sycamore

The Trusted Agent Operating System

Sycamore: The trusted agent operating system for the enterprise.

Progressive Trust SystemAdaptive System GenerationContinuous ImprovementCollective IntelligenceTrust by designSecureCompliantAuditable
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