Deployment Strategist

About the role

The 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.

Responsibilities

• 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

Requirements

• 2+ years in an implementation, deployment, or onboarding role at a SaaS company
• Direct, hands-on experience running the full implementation lifecycle for a software product
• 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

Qualifications

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