THE OPPORTUNITYThe Deployment Strategist owns the post-sale technical and operational journey for new customers - from initial configuration through go-live to early adoption. This is a project-ownership role: you are responsible for hitting deployment milestones and go-live dates, not just holding a relationship. You sit between the sales handoff and the customer success team, and you are the person accountable for a customer's first experience actually running on the product.
WHAT YOU'LL DO- Run kickoff calls and set expectations with new customers on scope, timeline, and what a successful deployment looks like
- Own the end-to-end configuration and setup of the product for each new account
- Build and manage a deployment project plan, keeping timelines, stakeholders, and internal teams aligned to hit go-live dates
- Present deck overviews and progress updates to customer stakeholders, from operators to executives
- Troubleshoot and resolve technical and workflow issues that come up during implementation, without routing them elsewhere
- Train end users and ensure the product is actually being adopted, not just installed
- Identify and flag risk early when a deployment is falling behind, or a customer is disengaged
- Hand off cleanly to the Customer Success team once a customer is live and stable
- Provide feedback to product and engineering based on patterns seen across deployments
WHAT WE'RE LOOKING FOR- 2+ years in an implementation, deployment, or onboarding role at a SaaS company (title may vary: Implementation Specialist, Onboarding Manager, Deployment Strategist, Technical Onboarding Manager)
- Direct, hands-on experience running the full implementation lifecycle for a software product - not just supporting one
- Comfortable running structured kickoff calls, presenting to stakeholders, and managing a project plan independently
- Track record of hitting deployment deadlines and can speak to specifics (number of implementations run, average time-to-go-live, customer count)
- Strong ownership instinct - when something breaks, or a customer is stuck, you solve it yourself rather than escalating
- Comfortable learning a technically complex product quickly and becoming the go-to expert on it
- Strong written and verbal communication; able to translate technical detail into plain language for non-technical stakeholders
- Organized and deadline-driven; able to run multiple concurrent deployments without dropping details
- Based in or willing to relocate to the NYC area; this is a five-day-a-week in-office role
WHY PROBOOK- The Tailwinds: $700B industry with clear tailwinds: AI adoption, labor shortages, and generational transitions creating demand for operational modernization. We are defining the category, not fighting for share.
- The Traction: $XXM ARR in 18 months. Product-market fit proven; now we're scaling.
- Funding: $40M raised from Sequoia and Andreessen Horowitz
- The Team: >60 people, our founding team comes from the space and has spent thousands of days onsite with our customers. We live the space. We're also becoming one of the most talent-dense start-ups in NYC (MIT, Harvard, UPenn M&T, Waterloo, Citadel, Palantir).
Compensation & Benefits- Equity: Meaningful early-stage equity.
- Salary: $110,000 - $130,000 (Can flex depending on YOE)
- Health: Comprehensive medical, dental, and vision.
- Perks: $500 monthly Ramp card for commuting, meals, gym, etc. (plus $25 in nightly meal delivery credit) and really good office snacks.
- Access: Direct access to world-class investors and advisors.
