Head of Implementation

About the role

We're hiring a Head of Implementation to own how Probook gets customers live and keeps them successful. You'll lead our Deployment Strategist and FDE teams (roughly a dozen people today and growing) and build the operating system for delivery: a repeatable methodology, clear stage gates, and a capacity model that lets us scale without running hot. The team is talented but stretched, and implementation today is high-touch and under-structured. Your job is to bring order, repeatability, and scale: tighten the process, raise the bar on quality, work down the remediation backlog, and partner with our emerging Customer Success function on clean handoffs. This is a hands-on, in-the-field leadership role, so you'll be on-site with customers regularly. You'll report directly to the Chief Customer Officer.

Responsibilities

• Process & Methodology: Own and document the end-to-end implementation lifecycle from kickoff through hyper-care and steady state, with explicit stage gates and quality checkpoints that reduce corner-cutting and rework.
• Team Leadership & Enablement: Directly lead the Deployment Strategists and Deployment Engineering teams: set goals, coach, manage performance, and build onboarding and enablement as the team scales. Clarify roles and rebalance an overloaded team.
• Capacity & Operations: Build a capacity-planning and resourcing model tied to pipeline and backlog, and stand up reporting on time-to-live, quality, rework, and onboarding health.
• Remediation: Bring structure to the re-deployment program, remediating accounts that need to be brought up to standard.
• Cross-Functional Partnership: Define clean handoffs to the emerging Customer Success function, and coordinate with Support and Engineering on escalations and technical dependencies.

Requirements

• You've led complex, high-touch enterprise implementations and you know what great delivery looks like.
• You're a process builder at heart. You define stages, acceptance criteria, capacity models, and repeatable playbooks, and you make "live" mean the same thing every time.
• You're a proven people leader who has managed implementation, deployment, or professional-services teams, and you genuinely level people up through coaching and enablement.
• You've both built a team from scratch and turned around a team in disarray, and you're energized by doing both at once.
• You're comfortable in ambiguity and resource-constrained environments, and you'd rather install structure than wait for it to appear.
• You're NYC-based, comfortable in-office, and happy spending a large share of your time on-site with customers.
• NYC Based: Live in (or relocate to) the NYC area, comfortable in-office and ~60% client-facing.
• Enterprise implementation experience, having led complex, high-touch enterprise deployments end-to-end.
• B2B SaaS background, with a strong understanding of SaaS delivery dynamics.
• Proven people leadership of implementation, deployment, or professional-services teams.
• Demonstrated process-building: stages, acceptance criteria, capacity models, and repeatable playbooks.
• Comfortable with travel up to ~40% of the time.
• Strongly Preferred
• You've stood up a team from scratch and turned around a team in disarray.
• You've stood up or partnered closely with a Customer Success function.
• You've managed remediation or re-deployment programs at scale, and operated in a high-growth, scaling post-sales org.
• Nice to have: experience in the home-services vertical (helpful, but explicitly not required).
• 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 equity, on top of cash OTE.
• Salary: Up to $300K OTE (75% base / 25% variable).
• Health: Comprehensive medical, dental, and vision.
• Perks: $500 monthly stipend (food, gym, Uber, etc.), plus $25

Benefits

Additional Information

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.

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