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Salary: USD 110,000 - 130,000 / annual
Probook is an AI Operating System for the home services industry (plumbing, HVAC, electrical), automating dispatch and operational workflows to improve customer outcomes and reduce manual staffing needs.
As Deployment Strategist, you own the post-sale technical and operational journey for new customers. You are the bridge between sales and customer success, accountable for hitting deployment milestones and ensuring successful go-live. This is a project-ownership role with direct accountability for customer outcomes.
Key responsibilities:
- Run kickoff calls to set expectations on scope, timeline, and success criteria
- Build and manage deployment project plans, keeping stakeholders and internal teams aligned
- Present progress updates and overviews to customer stakeholders (operators to executives)
- Troubleshoot and resolve technical and workflow issues during implementation independently
- Train end users and drive product adoption beyond installation
- Identify and escalate deployment risks early
- Hand off cleanly to Customer Success once customers are live and stable
- Provide product and engineering feedback based on deployment patterns
You bring 2+ years of hands-on implementation, deployment, or onboarding experience at a SaaS company. You have run full implementation lifecycles independently, not just supported them. You are comfortable with structured stakeholder communication, project management, and learning complex products quickly. You have a strong ownership instinct—when something breaks, you solve it rather than escalate. You are organized, deadline-driven, and capable of managing multiple concurrent deployments.
Probook has achieved $XXM ARR in 18 months with $40M in funding from Sequoia and Andreessen Horowitz. The team is 60+ people, many from the home services space with deep customer knowledge. The company is building one of NYC's most talent-dense startups.
This is a five-day-a-week in-office role based in the NYC area.
