Deployment Strategist

Probook; Manhattan (KS); On-site; USD 110,000 - 130,000; Full time

Benefits offered by this job

Equity

Salary

Health

Perks

Access

Job summary

Probook, the AI Operating System for home services, is hiring a Deployment Strategist in NYC. You own the post‑sale journey from configuration to go‑live, coordinating across sales, onboarding, and success teams to ensure a smooth deployment.

You’ll run kickoff calls, manage deployment plans, present progress to stakeholders, and hand off to the Customer Success team once live. This role requires strong project leadership, hands‑on implementation experience, and the ability to drive adoption

Qualifications

• 2+ years in an implementation, deployment, or onboarding role at a SaaS company.
• Hands-on experience running full implementation lifecycle for a software product.
• Comfortable leading kickoff calls and presenting to stakeholders.
• Proven track record of meeting deployment deadlines and go-live dates.
• Strong ownership and problem-solving without escalation.
• Ability to learn a technically complex product quickly.
• Excellent written and verbal communication; translate technical detail for non-technical stakeholders.
• Organized and able to run multiple deployments without dropping details.
• Based in or willing to relocate to NYC; in-office role five days a week.

Responsibilities

• Run kickoff calls and set expectations with new customers on scope, timeline, and success criteria.
• Own end-to-end configuration and setup of the product for each account.
• Build and manage a deployment project plan with timelines and stakeholders.
• Present progress updates to customer stakeholders, from operators to executives.
• Troubleshoot and resolve issues during deployment, without routing to others.
• Train end users and drive product adoption, not just installation.
• Identify risk early when deployment falls behind or customer disengages.
• Hand off to Customer Success once the customer is live and stable.
• Provide feedback to product and engineering based on deployment patterns.

Skills

Implementation lifecycle

Project management

Stakeholder presentation

Technical onboarding

Kickoff calls

Time management

Job description

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 — 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 installedIdentify 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.