Head of Onboarding & Implementation Strategy

Rentvine, LLC.; Fort Myers (FL); Hybrid; USD 180,000 - 240,000; Full time

Job summary

Rentvine is seeking a Sr. Director to lead onboarding across our two product lines, shaping how data migration, configuration, and live portfolios are delivered to customers. You will define the operating model, pricing, and SOW framework, and own the end-to-end implementation lifecycle.

You\'ll manage a cross-functional team, align with Finance and Sales on margins, and scale throughput with process, tooling, and AI, while maintaining exceptional customer outcomes and retention.

Qualifications

• 10+ years in professional services, implementation, or onboarding, with 5+ leading leaders in a B2B SaaS environment.
• Direct experience owning a services P&L or cost-to-serve model — you can talk about margin, utilization, and scope creep in specifics
• Built or meaningfully reshaped a pricing and packaging model for services, not just executed against someone else's
• Comfortable writing and negotiating SOWs, and setting the guardrails others work inside
• Has integrated teams post-merger or post-reorg, and can speak to how they handled the people side
• Data migration fluency — enough to be credible with the technical team and honest with the customer
• Runs clean handoffs across functions — you've owned a stage in a lifecycle, not a silo, and can partner with an education team you don't control
• Vertical SaaS or SMB-to-mid-market experience preferred; property management, real estate, or fintech a plus
• Track record of scaling output without proportional headcount growth

Responsibilities

• Onboarding delivery for Rentvine and PMW. One team, one model. Data migration, configuration, and technical go-live across both products, including the integration of two teams into a single operating structure.
• Time-to-live. Own the implementation timeline through go-live and the handoff into customer education, who takes the customer from live to proficient.
• Implementation economics. Cost-to-serve modeling by segment and package.
• Pricing and packaging for onboarding. Design the tiers, define what's included versus scoped, and set the pricing model. Partner with Finance and Sales on approval thresholds and margin targets.
• Scoping and SOWs. Author the SOW framework, run the scope approval workflow, and be the escalation point on non-standard deals.
• Capacity and efficiency. Scale throughput through process, tooling, and AI — not primarily through headcount.
• The team. Lead and develop managers across both onboarding orgs; build the bench.

Skills

Leadership

Budgeting

Pricing strategy

SOW negotiations

Data migration

Job description

Rentvine is seeking a Sr. Director to lead onboarding across our two product lines, shaping how data migration, configuration, and live portfolios are delivered to customers. You will define the operating model, pricing, and SOW framework, and own the end-to-end implementation lifecycle.

You\'ll manage a cross-functional team, align with Finance and Sales on margins, and scale throughput with process, tooling, and AI, while maintaining exceptional customer outcomes and retention.