Deployment Strategist
Probook · New York City · $110,000–$130,000 (stated in the posting)
ABOUT PROBOOK
Probook is the AI Operating System for the home services industry, transforming how plumbing, HVAC, and electrical businesses operate.
Our impact is real. Dispatching the right technician to the right job can mean the difference between a $300 "band-aid" fix and a $20,000 system replacement. By automating previously high-touch workflows around-the-clock, Probook ensures a consistent customer experience without the need for 24/7 live staffing. We unify our customers' processes into a single, scalable platform, giving businesses one place to run their entire dispatch operation.
THE OPPORTUNITY
The Deployment Strategist owns the post-sale technical and operational journey for new customers. 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
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.
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