Senior Director of Onboarding

Rentvine LLC; Fort Myers (FL); Hybrid; USD 150,000 - 210,000; Full time

Job summary

Rentvine LLC is seeking a Sr. Director of Onboarding to lead end-to-end onboarding across Rentvine and PMW, owning the scope, pricing, and packaging.

You will design the operating model, drive data migration and go-live, and partner with Finance and Sales to set margins and guardrails while building a scalable, cross-functional onboarding organization. The role is based in Bonita Springs, FL with remote options for nearby markets, requiring monthly travel to the Bonita Springs office for

Qualifications

• 10+ years in professional services, implementation, or onboarding.
• Direct experience owning a services P&L or cost-to-serve model.
• Built or reshaped pricing and packaging model for services.
• Comfortable writing and negotiating SOWs.
• Has integrated teams post-merger or post-reorg.
• Data migration fluency.
• 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.
• Time-to-live: manage implementation timeline through go-live and handoff to customer education.
• Implementation economics: cost-to-serve modeling by segment and package.
• Pricing and packaging for onboarding. Define tiers and pricing model; collaborate with Finance and Sales on thresholds and margins.
• Scoping and SOWs: write framework, manage approvals, and handle non‑standard deals.
• Capacity and efficiency: scale throughput via process, tooling, and AI.
• Lead and develop managers across onboarding teams; build the bench.

Skills

Professional services

Leadership experience

SaaS onboarding

SOW negotiation

Cost-to-serve

Pricing strategy

Data migration

Job description

company

About Rentvine

Rentvine is the fastest-growing property management software company in the industry, ranked #60 on the 2025 Inc. 5000 list. Our powerful, cloud-based platform helps property managers streamline operations, reduce manual work, and deliver a better experience for tenants and owners. Behind that innovation is a team-first culture that puts people at the center. We care deeply about building a company where smart, driven individuals can grow, feel supported, and do the best work of their careers. Our people aren't just part of our success—they're the reason for it.

Please Note: Rentvine is unable to provide employment sponsorship now or in the future for this position. Candidates MUST currently reside in the locations mentioned to be considered.

role

About the Role

Rentvine is property management software built for property managers. Onboarding is where a customer's decision to switch becomes real — data migrated, systems configured, portfolios live, website built. We're hiring a Sr. Director to lead onboarding across our product lines and to own how onboarding is scoped, priced, and packaged. You'll run implementation delivery end to end, and you'll own the commercial model behind it: service tiers, pricing, SOWs, and cost-to-serve.

It's a builder's seat. The teams and the customers are already here. The operating model and the services architecture are yours to design.

What You'll Own

• 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. Move faster without trading away the quality that drives our retention.
• 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. Keep Sales fast without letting scope walk.
• 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.

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

Location / Travel Requirements

• This role is based onsite/hybrid at our Bonita Springs, FL office, which is our preferred setup.
• We're also open to remote candidates based in one of these metro areas:
• Tampa, FL
• Miami, FL
• Orlando, FL
• Fort Myers, FL
• Atlanta, GA
• Remote hires will travel to our Bonita Springs, FL office once a month for 3-5 days to work in person with the rest of the leadership team. This is a recurring requirement, not occasional. All travel expenses are covered.

#LI-Hybrid #LI-DN1