The RoleWe'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.
Who You Are- 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.
What You Will Own- 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- 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).
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 in nightly meal delivery credit and really good office snacks.
- Access: Direct access to world-class investors and advisors.
