# Deployment Strategist at Sycamore

- Company: Sycamore
- What the company does: Sycamore Forge turns hard business processes into working software. Sycamore Guard governs every AI system from request to runtime. Backed by Lightspeed.
- Company website: https://sycamore.so/
- Type: Startups
- Level: Mid level
- Location: Bay Area
- Work setup: On-site
- Posted: 2026-10-21
- Apply by: 2026-12-05
- Apply: https://jobs.ashbyhq.com/sycamore/4b2bfbaf-37ae-49ff-a928-adc21ad7baa0?utm_source=1752vc&utm_medium=careers
- Page: https://www.1752.vc/careers/jobs/sycamore-deployment-strategist/

## About 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. Found on 1752vc Careers, the job board for startup and VC roles.

## What they're 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

Tags: GTM / Operations

Source: 1752vc Careers, https://www.1752.vc/careers/jobs/sycamore-deployment-strategist/